Today on The Late Bloomer Show, I’m coaching Dana.

Dana is a badass who’s never been in a relationship—and she came to our session asking the question so many late bloomers carry:

“Are men going to see that as a red flag?”

In this episode, we go deep and get tactical.

💎 We create her Essence-Based Preferences in real time (including the exact words she’ll use to vet potential dates)

💎 Build a clear vetting plan so she never has to waste a weekend on a “blah” date again

💎 Make over her dating profile so it reflects who she actually is: adventure traveler, joyful weirdo, emotionally aware, deeply feminist

We also talk through how to show up confidently when you feel behind, how to stop apologizing for your inexperience, and how to date like you’re not dead yet.

💥 Work with Lily:

→ Main Character Dating: datebrazen.com/waitlist

→ Free Essence-Based Preferences workbook: datebrazen.com/workbook

→ Read Thank You More Please: datebrazen.com/book

Follow Lily everywhere:
📲 Tiktok
📸 Instagram
📺 YouTube Channel

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Show transcript:

Lily Womble (00:01)

Hey, gorgeous friends, welcome to another episode of The Late Bloomer Show. I’m so glad that you’re here. Today, I’m coaching Dana, who is a badass, who also identifies as a late bloomer, and this episode is one that you’re not gonna wanna miss, okay?

So Dana, in her application, said the biggest challenge is constantly making excuses and not prioritizing dating, and this is a vicious trend time and time again. She also said, when I sacrifice my joy—time with friends, hiking, biking, doing yoga—for a blah date, I just get annoyed, discouraged, and then go months without dating.

Dana has never been in a relationship before that is long term, and she is wondering if it’s ever gonna be possible for her, if it’s over for her, and if she was gonna date, how would she do it considering all of the men who are really wrong for her?

Inside this episode, I not only help her blast past those mindset blocks, we co-create her essence-based preferences. We get them on paper. It is a really concrete coaching session. I then help her come up with a vetting system to help her vet dates to know whether or not they’re in alignment with her preferences. And then we make over her dating profile intentionally and with all of the self-knowledge.

And we make over her dating profile together with so much joy and alignment and power. So this is an episode that you’re not gonna wanna miss with Dana. And she left feeling completely different after this episode, after this just hour together. And I know you will too.

Lily Womble (02:16)

Hey, Dana, welcome to the podcast.

Dana (02:20)

Hi, Lily, thanks for having me today. ⁓

Lily Womble (02:22)

I’m asking everybody that I’m coaching before we get into it, what’s a brag—any sort of celebration—and what’s your intention for this session? What do you want out of this?

Dana (02:32)

A brag, a brag is that I made it here. And you see my background in my healthcare career—I’m passionate about my job—but I am ready to deep dive into dating, everything you know about being a late bloomer, and all the things from your podcast. You know, perfectionist, career goal setting…

Lily Womble (02:58)

Yeah.

Dana (02:58)

…but dating has been on the back burner.

Lily Womble (03:02)

Yeah. And so what’s your desire for this session? Like if you could ask for a magic wand, really concrete outcome, what do you want?

Dana (03:11)

Well, I would say long-term concrete outcome would be a partner, a life partner. Short-term goal would be really to get back into the dating game. There’s a wall right now. I’m just resistant to get back into it and I want to enjoy it. I want to look forward to it. I want to do it so it’s not something that I feel is dreadful right now in my life.

Lily Womble (03:39)

Mmm. Yeah, okay. Not dreadful. Okay, great. That’s a great, great ⁓ minimum goal.

Dana (03:48)

Yeah.

Lily Womble (03:50)

So I want to read from your application—with your permission, obviously. You said the biggest challenge is constantly making excuses and not prioritizing dating. And this is a vicious trend time and time again. You have a mentally demanding job in healthcare, and the last thing you want to do after work is shoot the shit with a random tech bro. Tell me about this vicious cycle that you have found yourself in. How long has it been going on?

Dana (04:18)

I’d say most of my career, which has been about 10 years. I went full on—I moved from the East Coast to California. So that was a big transition to start a career. So it was like the big move, starting my career.

Really demanding first job at Planned Parenthood, which ⁓ I didn’t realize this, but my friend thinks I have a lot of trauma from that. Seeing a lot of shit working as a PA at Planned Parenthood. And so that made me—like I was always a feminist—but that made me more of a feminist. Like, you know, boys suck, I’m gonna be single my whole life. But really, I didn’t want that.

Lily Womble (05:05)

Yeah.

Dana (05:10)

And then after that job I moved, still in California, for a fellowship. So I just focused on that. And then I moved to Oakland, where I’m now living, to start a new job there. And I was only here for a year before COVID hit.

So I just always think there were a lot of transitional changes and, ⁓ you know, I dabbled with dating, would go on a few dates but nothing really stuck. And then I do prioritize fun ⁓ on the weekends, but I call myself a weekday grandma and a weekend warrior. So weekdays I’m just always tired after work, and then weekends I’m just like going non-stop. And so it’s finding the space to date between that.

Lily Womble (05:51)

Yeah. Okay, got it. Like living-for-the-weekend kind of vibes. Okay. Normal, normal, normal, especially as a healthcare professional and a PA.

Okay, so I just want to touch down on something that you said about feminism and working in Planned Parenthood and just realizing how much deeper that feminist value system goes for you. And you said, I’m a feminist, boys suck, and…

Dana (06:06)

Yes. Yes.

Lily Womble (06:29)

…you know, but I really wanted a relationship. And I think that’s a really common mindset that a lot of folks get into, which is that the very understandable anger toward a lot of men—who do suck.

They exist. And the ⁓ sort of hegemonic, power-over dynamic that our patriarchal culture continues to espouse and continues to socialize us within, which is male dominance, and then that trickles down into all sorts of behavior that sucks.

We can—I want you to hate, like that sucks. We need to imagine and build a different world. And I think that, that, you know, easier said than done, but like one step at a time as a collective. Both/and.

Feminism, to me, does not mean hating men or not wanting a relationship. Wanting a relationship is not mutually exclusive with feminism. Wanting a relationship does not make you a trad wife.

Dana (07:29)

Mm-hmm. Yeah.

Lily Womble (07:38)

Like, you know, we are human beings who exist in community with one another. We crave more community. We crave more belonging. Why wouldn’t you want a romantic partnership? Sounds fun.

Dana (07:49)

Mm-hmm. Yeah. Yeah.

Lily Womble (07:52)

How does this land for you?

Dana (07:55)

It sounds fun when you meet that right person. Yeah, when I observe relationships, whether it’s friends or patients, I’m like…

Lily Womble (08:00)

Yes.

Dana (08:09)

I would say more times than not, like, I don’t want that. But there are some relationships where I’m like, yes, they are it. They’re doing their thing. They’re vibing. This is a great couple. I would love that. Like that’s my goal, to find that relationship that is healthy and fun and just beautiful.

Lily Womble (08:32)

Yeah. Have you been in a relationship before?

Dana (08:36)

No.

Lily Womble (08:37)

Tell me about that. How do you relate to that?

Dana (08:38)

I think it’s definitely an insecurity, for sure. Feeling, you know, the whole late bloomer thing—that I don’t know what I’m doing. And that, you know, in my advanced maternal age, where I do want a family, yeah, feeling like, you know, will I know what I’m doing when the time comes?

Will I dismiss it? Just feeling behind, I think.

Lily Womble (09:09)

Yeah, and I’m hearing kind of the fear that you’re cursed a little bit, like you won’t — even if it comes, you won’t know what to do with it, or you’re gonna miss your chance. Does that resonate?

Dana (09:19)

Mm-hmm. Mm-hmm. Mm-hmm.

Lily Womble (09:23)

Tell me about that, like what comes up when I say that.

Dana (09:26)

Yeah, I guess, you know, there’s fear there for sure when that conversation comes up. And I think you just actually had a podcast about this — when I have that conversation, “When was your last relationship?” I kind of freeze. And it’s kind of like, why? What are they going to second-guess about that? Are they going to look at that as a red flag?

For me, if someone were to tell me that, I wouldn’t necessarily think it’s a red flag. I would just be more inquisitive to want to learn more. Like, did you prioritize your career like I did? Did you, you know, have family issues, or whatever it is? But I just think, like, looking from…

Lily Womble (10:00)

Mm-hmm.

Dana (10:11)

…the male perspective, that they might look at that negatively.

Lily Womble (10:16)

Mm-hmm. Mm-hmm. Yeah, it sounds like the character of men in your mind is sort of like… they’re not a great group to — like on the whole, it sounds like your brain has sort of decided that it’s unsafe or unwise to trust that some might be kind or understanding, like you are kind or understanding. Does that feel kind of impossible in your current mindset?

Dana (10:46)

Not impossible, but hard.

Lily Womble (10:50)

Why? Tell me about that.

Dana (10:53)

I think it’s changing. I think my generation — the men are changing and are becoming more emotionally intelligent. But not all of them are. Not all of them are. So it’s like, when a male is vulnerable on a first date, I find that attractive. When they say like…

Lily Womble (11:06)

Correct.

Dana (11:18)

…“I’m struggling with this,” right? Or, “I spoke with my therapist about this.” It’s like — that’s a green flag. You are in therapy. Yeah. Yeah.

Lily Womble (11:24)

Absolutely, absolutely. So are you vetting for that before you meet somebody?

Dana (11:31)

No, I don’t. I don’t know. I mean, I don’t know if anyone in their profile would be like, “Hey, I’m in therapy.”

Lily Womble (11:39)

Okay, so here’s what I’m listening for, Dana. Because I just want to give you really concrete next steps today so that you can get back into dating and start pursuing your desire wholeheartedly.

Dana (11:43)

Yeah. Yeah.

Lily Womble (11:58)

Because it sounds like this has been on your mind for a really long time and that you’ve, as you’ve expressed, felt like you’ve been in a vicious circle, vicious cycle. And I want to pop you out of there. Like, this is what you want — it’s possible. It is not too late, and it will require you to do something different. So are you willing to do something different?

Dana (12:06)

Mm-hmm. Mm-hmm. Yeah.

Lily Womble (12:19)

Great, great. Here’s what I’m listening for: I’m listening for friction in your love life, in what you want, and your difficulty believing that it’s possible. I’m listening for friction.

Whenever I hear friction — for example, what I’m hearing you say is that you want to find somebody who’s emotionally mature, who is a man, you’re dating men it sounds like, and that you want to date men who’ve done emotional work. Maybe they’ve gone to therapy, maybe they are reading great self-help books, or they’re getting coaching, or they’re listening to a podcast about male friendship and building them, right? Like that’s the kind of man — in one of your essence-based preferences — you want to feel inspired by and seen by, this person who is doing their emotional work, like I imagine you have done and are doing your emotional work. Yes?

So then when I listen…

Dana (13:06)

Mm-hmm. Mm-hmm. Yeah.

Lily Womble (13:15)

…what I listen for is: friction for you is that you don’t believe. You believe that they are very few, maybe really rare, that you’re not going to meet them. Yes or no?

Dana (13:26)

Yeah.

Lily Womble (13:27)

And that even if you are dating, you can’t vet for that early because it’s too intense a question to ask, or they’re not gonna put it in their profile. So do you see how that’s like a double bind you’re putting yourself in? You want something, it’s a struggle to believe it, but then you’re not vetting for it before you’re meeting somebody because you don’t think you can. So of course you would be in a vicious cycle of going on mediocre dates.

Dana (13:52)

Yeah. So vetting for that.

Lily Womble (13:58)

Well, yes, micro, macro. I want to hear everything that you find friction-forward in your dating life, and there’s a fix for it.

Dana (14:12)

Mm-hmm.

Lily Womble (14:12)

If the friction is — you said in your application: “When I sacrifice these joys, which is weekend time, friend time, hiking, biking, doing yoga. When I sacrifice these joys for a blah date, I just get annoyed and discouraged and go months without dating.”

So let’s increase the quality of the dates you’re going on by shoring up your preferences and your vetting process.

Dana (14:33)

Mm-hmm. Mm-hmm.

Lily Womble (14:34)

Do you see how we’re looking for the friction and coming up with a solution, which is rooted in self-permission rather than, “Well, this is just impossible,” and you have to do the needle-in-the-haystack thing of like, “Gotta go on all these bad dates to find a good one. I have to kiss all these frogs.” No, no, no, no, no. You don’t have time for that.

Dana (14:50)

Mm-hmm. Yes.

Lily Womble (14:55)

What are you thinking? Give me — like, I thrive on your thoughts and feedback, so tell me.

Dana (14:58)

Yeah. Yeah, I mean, I love that idea: vetting them. And I like — I sort of want to cut through the bullshit with like the quick back and forth when we met. But I also… and I feel like a lot of men are not honest in their profiles.

Lily Womble (15:23)

Mm-hmm.

Dana (15:24)

And that is a struggle for me too. I feel like when I meet them in real life, they’re not who they portray themselves to be.

Lily Womble (15:35)

Tell me in what regard it’s generally coming up. Is it height? Is it age? Is it something else?

Dana (15:38)

Well, one thing I’m very passionate about: I call myself an adventure athlete. So I love to travel and I love to be an athlete. And so like people pretend they’re outdoorsy in the Bay Area, but they’re really just working at their startup, you know, 12 hours a day. And that’s not their priority.

And so like — I actually think it was your podcast that mentioned to ask them, “What brings you joy?” pretty early on. And so even just like a few quick messages, I’ve started asking that. I think that’s a great vetting question. And then they don’t have a response. And so I’m just like, okay, next.

Lily Womble (16:10)

Yeah. Yeah, well, that’s a good…

Dana (16:26)

Like, “I don’t know, I’ve been working so much,” or, “You know, life’s been stressful.” Yeah, no shit. It has.

Lily Womble (16:34)

Yeah. Well, they are automatically disqualified.

Dana (16:38)

Yeah.

Lily Womble (16:41)

And coming from my perspective — I know it’s easy to say from somebody who’s not in your shoes, and I’m gonna say it anyway: your job is to become unbothered by the wrong people for you.

And what I think might be happening now is that you are perceiving a lot of people who are wrong for you, especially on dating apps. And then with your perception of how many people are wrong for you, it becomes an assumption that you’re making: “This is all. There’s nobody for me. It hasn’t happened now, why would it happen? I don’t like any of these people, why would I continue?”

When I’m coming from the perspective of: a dating app is just a silly little tool that has the potential to connect you with somebody cool. But you’re for the few, not for the many. So most people are going to be absolutely wrong for you. Most people are not — I think of like, everything is a spectrum.

Dana (17:23)

Mm-hmm. Mm-hmm. Mm-hmm. Yeah.

Lily Womble (17:46)

So outdoor adventure is a spectrum. You might be a 9 out of 10 on outdoor adventure. Tech bro who works 12 hours at his desk might be a 1 out of 10. You probably need a 6+ or 7+ out of 10. So it’s a spectrum, and people don’t know.

Like, this is why I love Essence-Based Preferences and helping you create your own bespoke definition. Because they might really believe that they’re outdoor adventurous, but their definition would be very different than yours. So you’re looking for somebody who has an aligned definition like you — like a 6, 7.

Dana (17:46)

Right. Yeah. Mm-hmm. Mm-hmm.

Lily Womble (18:15)

Which is why we need to vet for that. And those people are going to… You’re for the few, not for the many.

Dana (18:18)

Yeah. Yeah.

Lily Womble (18:35)

How is this striking you?

Dana (18:37)

No, I — yeah, that makes perfect sense. Yeah.

Lily Womble (18:42)

So let’s get to your — let’s talk about your preferences. Are you game if we like bang them out right now? Okay, cool. Do you have essence-based preferences yet? Have you created those?

Dana (18:45)

Okay. Yeah, let’s do it. Let’s bang it. I thought about it when I read your book. But I — you know, now that I’m on the hot seat, I can’t remember it, but I’m sure I could think of some now.

Lily Womble (19:03)

That’s okay. That’s okay. We’ll come up with some together.

If anybody listening wants to do this with us, you can go to datebrazen.com/workbook to get the Essence-Based Preferences creation guide.

So for anybody that doesn’t know: Essence-Based Preferences are like beneath the surface of a checklist. It’s your living, breathing documentation of what you want. So what would make you come alive across the table? Not just on a logistical level — though we can talk about, like, okay, you want this logistical age range, how do you hope that makes you feel?

But putting that aside for a second: the values and personality traits that you want. We need to create your own definition of those that is full of how you want to feel in the presence of somebody with that trait or value, so that you can more adequately know what vetting questions to ask, and so that you can more adequately find better people for you.

So everything builds on itself. Let’s start with the adventurous outdoor piece, because that feels important to you.

Dana (20:04)

Mm-hmm. Yeah, definitely.

Lily Womble (20:06)

What is a root word or phrase that we could use to describe this preference? Is it like outdoor athlete or like adventure? And do you need somebody who is also an athlete? Do you want that?

Dana (20:18)

Not necessarily. I would say adventure traveler because I want—I like traveling too, like international traveling.

Lily Womble (20:25)

Okay, got it.

Okay.

Okay, what kind of adventure do they pick when they’re picking a travel adventure? Ideally, if you asked them, “What was the last trip you went on?” and they gave you this answer, it would really make you see that you were kind of aligned in this preference.

Dana (20:38)

Yeah.

Yeah, yeah. So I would say like a cultural immersion outside of the country, doing something physical, whether it’s backpacking or hiking or biking or even like a yoga retreat maybe.

Lily Womble (21:06)

Okay.

Mm-hmm, cool, love it. And then how do you hope to feel in the presence of somebody who is this kind of adventure traveler?

Dana (21:20)

What I hope to feel with them doing this?

Lily Womble (21:22)

Yeah, how do you hope this preference makes you feel in their presence, right? When you meet somebody who is similarly, like really aligned in this, how do you feel in their presence?

Dana (21:32)

Yeah, like a best friend, like a best friend adventure buddy.

Lily Womble (21:39)

Amazing.

So what I’m hearing is like seen, safe, inspired.

Dana (21:47)

Mm-hmm.

Lily Womble (21:49)

Right? This isn’t somebody that you’re like neutral about or like, “Yeah, they do some cool things.” You’re like actively turned on by their interest in this. Does this resonate?

Dana (22:02)

Yeah, totally.

Lily Womble (22:04)

Cool. And then I think we should put something in there about like the spectrum of—like what’s the minimum acceptable number on the one to 10 spectrum of outdoor adventurer or adventure traveler that would be right for you? If one or zero on the spectrum is—no shade, people, all people have different preferences. There’s no judgment toward anybody, but maybe a zero is somebody whose ideal vacation every year is like a trip to a resort and staying at the resort and sitting by the pool for a week. That’s maybe one or zero. And 10 is like Victoria Falls, Kilimanjaro, going and skydiving, whatever. Where are you and where do you ideally want somebody else to land?

Dana (22:47)

Thanks. I would say I’m pretty—I would say like nine for me and I would want them to be at least a six.

Lily Womble (22:57)

Yeah.

Cool, what does six look like, maybe?

Dana (23:06)

They’re passionate about traveling. They like to have an active lifestyle. They might not need to be as extreme as me, which might actually be nice. Like I actually did Kilimanjaro last year by myself. But someone who’s like, “Hey, like—well, then I did a beach thing in Zanzibar—but like, hey, let’s do this. But like, we don’t have to be so extreme all the time.”

Lily Womble (23:17)

Yeah! Congratulations.

Yeah, so a little bit of balance. Love that. I love that. Okay, so now we have—I’m holding up the sticky note that I took notes on—we have your first EBP, Essence-Based Preference. I wanna get to three to five root words. We may not get to them today, but I want you, after this call, separately to complete that workbook, and I can send it to you. It’s also in my book Thank You More, Please as well. But I want you to have this love life vocabulary for yourself, because I would imagine that you haven’t spent much time on the best-case scenario.

Dana (23:37)

Yeah.

Mm-mm.

Lily Womble (24:05)

And it’s time to. Your worst-case-scenario planning has had a lot of exercise. It’s like if you were to work out just your quads, you know, they’d get really big and other parts of your body might feel weaker. You have not spent enough time thinking about what you want and your best-case scenario because of the fear that it doesn’t exist.

Dana (24:09)

Yes.

Yeah.

Yeah.

Yeah. Yep. Mm-hmm.

Lily Womble (24:29)

But here’s the deal, you’re not dead yet. One day you will die. One day you will die, I will die, we will all die. But you’re not dead yet. So I’m not gonna let you live like you’re dead in terms of like, it’s over. It’s not over. You don’t know that.

Dana (24:37)

Uh-huh. No? Yes. Yeah. Yeah yeah yeah. I like it.

Lily Womble (24:50)

Okay, let’s talk about your second essence-based preference. I think we should do something around emotional maturity or grounded confidence with emotional—like some emotional work. Like how are we gonna—what do you want in terms of the emotional awareness pieces?

Dana (25:08)

Yeah, I would say…I don’t—I mean, I don’t know if this is sort of a side tangent, but humor is important to me. I would want someone to make me laugh. And it sounds cliche, but I think humor is, you know, a big part of—like, if someone can make me laugh and…

Lily Womble (25:17)

Yep, tell me.

Mm-hmm.

Dana (25:33)

When I think of like long-term, like partner that I’m gonna die with, the Notebook couple, I want someone who can keep me on their toes, keep me on my toes and make me laugh. Yeah. I don’t know. I don’t know.

Lily Womble (25:48)

Yeah, cool. What type of humor do you like? What comedians, podcasts, TV shows? Like what’s your brand?

Dana (25:58)

I would not say dark, like just silly, goofy, like spontaneous, like quick-witted person, like not trying too hard to be funny. That’s why I loved improv because you know, you have to think on your feet. You have to just be spontaneous versus, you know, a stand-up, it’s like, it’s pretty rehearsed.

Lily Womble (26:05)

Whoa.

Huh?

Yeah.

Mm-hmm. You know what strikes me about improv and how you bring it up and how I love improv too, as you know, but it’s connective. It’s not a monologue at you, it’s a conversation between you. So it’s like somebody who listens well, who’s asking good questions, who’s like following up with something funny or clever, witty, in just kind of a fun, silly way, you know? So it’s connective. So I’m writing that down too. Like you feel this—like how do you want to feel?

Dana (26:32)

Yeah.

Mm-hmm.

Yeah.

Lily Womble (26:52)

Connected, right? Like joyful in their presence, like taken care of. When you’re in an improv scene with somebody that you don’t trust to land the plane or who is not very generous as a player, it can be very stressful. But when you’re with somebody who you trust to like—that you know that you’re in this together, that you’re going to be okay, like you’re doing something scary together—

Dana (26:53)

Yeah. Yeah.

Right.

Yeah.

I’m sorry.

Lily Womble (27:20)

—that’s connective and that’s like, you’ve got some ground-level trust.

Dana (27:25)

Yeah, totally, totally,

Lily Womble (27:27)

Yeah. So are there TV shows or like anybody specifically, do you like Parks and Rec? Do you like The Good Place? Do you like—okay, this is good to know about you. So you don’t watch TV. Do you watch any media or listen to podcasts?

Dana (27:31)

I actually don’t watch TV. Yeah. Or, not much, not much. I very much mean, yeah—being outside, traveling, exercising, yoga.

Lily Womble (27:48)

What are you doing for fun? I’m just curious. Amazing. Do you read?

Dana (27:58)

I’ve listened to audiobooks. Usually I’m hiking with an audiobook or spending time with friends, but I’m a very…

Lily Womble (28:05)

My God. As someone who is addicted to TV, I’m just like, I’m like…fun. This is so kind of unplugged. I’m a fan.

Dana (28:11)

I don’t know. I’m like the person where I—like I’m rarely in a hotel room, but I was in a hotel room in Boston in June and I was like, I don’t even know what to watch or what to order and I’m like Googling like, “Is this a good movie? I’ve never heard of it.”

Lily Womble (28:29)

Okay, somebody who—yeah, okay, this is so good and interesting. So TV and like pop culture, if somebody is like very pop culture-y, it may not resonate for you.

Dana (28:42)

Yeah, not so much. It’s not a deal breaker. I do—yeah, I do Instagram, Facebook, you know. But like someone who’s on video games all day might not be my vibe.

Lily Womble (28:44)

Yeah, are you on any social media? Okay. Cool, okay. This is really good information. This is really good. So the disqualifier for the humor piece would be, I would imagine, somebody really dark, sarcastic.

Dana (29:10)

Yeah, not necessarily. Sarcastic is funny. Like, I like the banter. Like, I like bantering with the person in a fun, loving way.

Lily Womble (29:11)

Would not be your vibe? Okay.

Banter, got it.

Are you looking for somebody who is generally seeking out the fun, seeking out the optimistic viewpoint versus, you know, more nihilistic? Okay, cool. This is all good to know. So like maybe more optimistic, grounded understanding of the world, I would imagine, but optimistic-ish with a healthy dose of realism, maybe? I’m saying things now. Okay, got it.

Dana (29:30)

Yeah. Yes. Yes, love it, love it. No, well said.

Lily Womble (29:52)

Healthy realism, cool. And by the way, I have several nihilists in my life who I love very much. Again, no shade, I’m reacting based on what I’m hearing you share. Okay, let’s talk about the feminist piece and the emotional awareness, emotional maturity pieces. Are those one and the same, like values-wise? Like tell me about which one you wanna talk about first.

Dana (30:12)

Yeah. Emotional maturity.

Lily Womble (30:21)

Okay, what does that look like to you?

Dana (30:24)

I think someone who is willing to be vulnerable.

Lily Womble (30:30)

Yep. How do you know when someone is willing to be vulnerable? What does that look like?

Dana (30:36)

Yeah, they’re open to having a conversation. They don’t just avoid. And they’re open to new perspectives. So yes, you can always listen, but if you’re not willing to hear the other side or—

Lily Womble (30:40)

Yep. Yep. Yep.

Dana (30:59)

—other people’s points of view, then you have to be… just like your mind has to be open, I think.

Lily Womble (31:06)

Yeah, yeah. So I would say the great vetting question for this preference might be like, what’s your favorite hot take? What’s your favorite unpopular opinion or something? And if you like disagree on something, how is it handled?

Dana (31:15)

Yeah. Right, right. Yeah.

Lily Womble (31:23)

Even if from the beginning, just lightheartedly, that can tell you a lot. I would also say willing to be vulnerable. Do you want to… sort of ideally, this person has been to therapy or something like that?

Dana (31:29)

Mm-hmm. Because it shows… Yeah. Yeah.

Lily Womble (31:41)

Yeah, because it shows—

Dana (31:44)

—because it shows, again, like emotional maturity or them wanting to better themselves. Yeah, self-awareness, yeah.

Lily Womble (31:51)

Self-awareness. Yeah, something that you can ask about with this preference before even a date is like, what’s your favorite thing you’ve learned about yourself this year?

Dana (32:02)

I love it.

Lily Womble (32:03)

Yeah, or what’s your favorite thing that your therapist says over and over and over again? Like something, you can add it lightheartedly, but it doesn’t have to carry with it like, do you go to therapy? Yes or no. But I do think that from the beginning, you are intentional about what you want. You, Dana, you know that you need somebody who has this like connective humor. These are all the root words that we’ve got so far: adventure traveler.

Dana (32:13)

Mm-hmm.

Lily Womble (32:31)

Emotional maturity. And you’re gonna vet for this. We’re gonna figure out this, we’re gonna help you with the system to vet for this after this. Okay, finally, is there anything we’re missing that you can think of?

Dana (32:39)

Mm-hmm. Mm-hmm. The independence too. I do not like codependent couples. I do think it’s important for any couple to have—

Lily Womble (32:47)

Uh-huh. Yeah.

Dana (32:58)

—you know, their separate friends, their separate hobbies, being able to do things on our own without needing to be attached at the hip at all times, without needing to ask everything like, hey, is it OK if I go out to dinner with my friend? Is it OK if I do this? Like just having our own likes and hobbies and lives outside of each other, I think is important.

Lily Womble (33:04)

Yeah. Yeah, cool. I’m hearing the vetting things within this category: friend group. So do you like to travel with your friends? When’s the last time you did something with your friends? Like making sure that they have friends that they care about. And how do they care about them? Tell me about that. You know, on a first date, you could totally ask something like that. Hobbies—they must have something that brings them joy and that they invest their time in. I think that goes into the self-awareness and self-care questions. Another question that I love people to ask is, how do you take care of yourself after a long hard day? What do you like to do to decompress, right? So these are how you vet for somebody who is the self-aware, independent, emotionally mature, adventurous traveler, humor piece. Values-wise, just like a feminist man, you know, especially with the context of you previously working in Planned Parenthood, I think it’d be really important. Does that feel resonant to you or not so much?

Dana (33:57)

Yeah. Yeah.

Lily Womble (34:22)

How would you describe that?

Dana (34:25)

Yeah, I mean, again, being politically aware. Like, I don’t really like to talk about politics, it’s sort of a side tangent, but also I think understanding the nature of my work and how tolling it can be. So having emotional support with that, like, you know, seeing 16 patients a day, dealing with emotional trauma, physical trauma all day long.

Lily Womble (34:43)

Yeah. Yeah.

Dana (34:56)

Having someone to come home to and being able to comfort me and being like, you know, I know you had a hard day. You know, so I don’t necessarily need to date a healthcare worker. I might not even prefer that, but someone who understands the nature of my work and what I do.

Lily Womble (35:02)

Right? Yeah.

Lily Womble (35:16)

This episode is brought to you by my free guide called the Essence-Based Preferences Creation Guide. You can get it at datebrazen.com/workbook. Inside this guide, I take you step by step through creating your essence-based preferences. EBPs, or essence-based preferences, are beneath the surface of your checklist. They are your love life vocabulary that describes exactly how you want to feel inside of the right relationship. And they make you magnetic toward that which is right for you. They help you vet people who are wrong for you out of your dating pool. They help you recognize when someone is right for you. So it eliminates any of that overthinking or anxiety and self-doubt in the process of dating so that you move forward faster.

You can fill out these essence-based preferences along with Dana and me in this episode by going to datebrazen.com/workbook to get your hands on this free guide. And you’ll also be on my email list where you get my feminist dating hot takes weekly. It’s a great place to be. So, go get your preferences workbook, start creating your essence-based preferences, because it’s your magnetic season, okay? And let’s fucking go. Now, back to the episode.

Lily Womble (36:27)

So I like this: politically aware, understands the nature of your work, and also like I would imagine pro-choice, pro-abortion-as-healthcare vibes. Is that resonant? Yeah, cool. And somebody who wouldn’t like actively hear about what you do and share their fucking hot takes about it, right?

Dana (36:38)

Mm-hmm. Yeah, yeah.

Lily Womble (36:56)

They hear what you do and the only appropriate response is, “My God, you’re a hero.” Do you know what I’m saying? Like you’re helping people.

Dana (37:02)

Yeah, yeah, I love that.

Lily Womble (37:06)

Anything else here that feels resonant to share or express for this preference?

Dana (37:13)

You know, back in 2020, we were considered heroes. I think that sort of has dissipated. Now we’re just, you know, back-of-the-line workers that still do the same thing, but it’s even worse in my opinion now than it was.

Lily Womble (37:19)

Yeah.

Dana (37:29)

You know, if he were in an industry of service, like a teacher or social worker, I find that or some type of field that is helping others—that’s a huge green flag for me.

Lily Womble (37:45)

Well, we need to add that to one of your preferences or make a new one. So I think like helping others could go into emotional maturity, but it also could be its own separate thing of like generous of spirit. Like that’s in the way that they have friendships, how they donate their time and/or money, how they think about the world and themselves within it, how they are aware of things going on in the world and how they actively care about them. How does this resonate?

Dana (38:18)

Yeah, being woke.

Lily Womble (38:20)

Yeah, being like, think just like—

Dana (38:25)

—doing something to make a difference. Like even if they’re not doing it for their career, you know they’re in tune, like maybe volunteering for a nonprofit or just having, yeah, having some awareness of what’s going on.

Lily Womble (38:44)

What kind of nonprofits ideally would they donate their time or money to?

Dana (38:48)

I don’t know. I don’t know. Yeah.

Lily Womble (38:50)

You don’t have to answer that if you don’t want to, yeah. For example, for me, I would want them to be donating to Doctors Without Borders for the humanitarian crisis in Gaza.

Dana (38:59)

Yes. Yeah, I would love that. Environmental. I’m like a big environmental sustainability [person].

Lily Womble (39:08)

That goes into the adventure traveler, right? That you’re not exploitative and you’re trying, I would imagine, trying not to be exploitative in the way that you travel, of the earth.

Dana (39:11)

Yeah. Yes, yes, yes.

Lily Womble (39:19)

And you’re thinking about that. Somebody who’s thinking about this, right? There are some people who you would ask this question, they’d be like, huh, I’ve never thought about it before. Those people probably wouldn’t be for you.

Dana (39:24)

Mm-hmm. Mm-hmm. Exactly. Like ecotourism. It’s sort of this sustainability type of mindset when you’re traveling, like looking for the company that might have better sustainability practices or, you know, when I hiked Kilimanjaro, there are certain companies that are approved by the society to say that they’re credible and they’re employing local porters. So yeah, having some eco-mindedness.

Lily Womble (40:01)

Yeah. Yeah, cool. Okay. Okay. So I think we’ve got a great lineup of essence-based preferences. We’ve got the connective humor, adventure traveler, emotional maturity, independence or grounded confidence—something about that, you can fine tune after this. Politically aware, or like human rights, or empathetic to the world and doing something about it in a small or big way. Empathy to others, cool. We can make that empathy. And like, I think the personal is political, so I think empathy can also be political, it can be interpersonal, it’s all of the above. And then the helping others could fit into one or more of these categories, but it could also be its own category.

Dana (40:35)

Yeah, empathy to others maybe. Mm-hmm. Mm-hmm. Yeah, I love them all. Feel good. I hope you write this down for me. Okay. Yeah, okay. I’ll make my own notes.

Lily Womble (40:57)

How do these feel?

I’ve written down some notes, and you’ll also be able to listen to this again and again. We’ll have the transcript and everything, so we’ve got you.

I want you to go into each of these categories after our call—or at some point soon—and flesh out: what does this look like ideally for them to be connective and improv-y on dates? Not that they have to do improv, but what kind of questions are they asking you? How are they showing up for you?

Dana (41:25)

In the air.

Mm-hmm.

Lily Womble (41:31)

All of this is ultimately about co-creation, Dana. The wrong men for you will not co-create. They will not ask questions back. They will only give one-word answers. They put all the emotional labor on you to carry a conversation, carry a date, check in afterward. They’re not for you.

Dana (41:36)

Yeah.

Yes.

Mm-hmm.

Mm-hmm. Yeah, the generic. The generics are no.

Lily Womble (41:53)

Let’s let the right people rise to the occasion and allow them to show you who they are. This will be both in person and online. So let’s talk about the vetting process, because the original friction you had expressed was that—

Dana (42:02)

Yeah.

Yeah.

Lily Womble (42:16)

You said, I need guidance, advice, a dating coach to navigate the complexity of dating. One who respects a woman’s independence, feminism, understands late bloomer mentality, and helps me get clarity and bring joy to a non-existent dating life. So let’s make your dating life existent. What do you want to do about it?

Dana (42:37)

What’s your advice to dive in and feel optimistic about it?

Lily Womble (42:44)

Okay, great. So, two-pronged approach: IRL dating and online dating. I’m going to encourage both for you because—especially for people who are healthcare workers, teachers, or single mothers—your schedule is very busy. So dating apps are a space that is very imperfect. They are not the answer, but they’re a space for you to meet somebody and set up a date. I would love if you chose, like—

Dana (42:54)

Mm.

Lily Womble (43:13)

—one weeknight a week to set aside for Pleasure Love Life Night.

Dana (43:16)

Mm-hmm.

Lily Womble (43:22)

On the nights where you don’t have a date, on that Pleasure Love Life Night, you are taking yourself on a date. To stop only living for the weekend, you do Pleasure Love Life Night. And when you get on a dating app, that will be your night to go on a date—if and when it comes from a dating app. Does that resonate?

Dana (43:28)

Okay. Okay. So the one night a week should be a date, or… okay.

Lily Womble (43:47)

With yourself, or with another human being who you meet through a dating app or IRL. Let’s just carve out that you’re making a night for your love life. And with your self-dates, you can work on your dating mindset. That’s another piece of this—it’s like the strategy and the mindset have to go together. So, how to not be so hopeless all the time? You can lean on the tools that I teach in this podcast, like—

Dana (43:52)

Okay. Okay.

Yes, okay, I like it.

Yeah.

Lily Womble (44:15)

SOFT: self-compassion, owning your needs, feeling your feelings, thoughts-not-facts. Do a brain dump of all your hopeless thoughts and take it through SOFT to coach yourself through hopeless moments, to bring more aliveness to this area. You get to be kind to yourself, own what you need, notice where it is in your body, allow it to rise, breathe into it. I’m willing to feel anything to be with you vibes—that’s a thought from Simba and Soul. And then “thoughts, not facts”: What else might be true? I’m trying something new.

Dana (44:45)

Yeah.

Lily Womble (44:47)

I’m learning how to have an alive dating life. I’m learning how to build more experience. I’m getting more clarity by showing up for myself. I’m not dead yet, I don’t know everything—so let’s fucking go.

Dana (44:58)

Mm-hmm. I love it. Yeah, I love it. Yeah.

Lily Womble (45:02)

Okay. And then strategy-wise, I want you on a dating app. And I want you to do one—not three. Let’s decide right now. I don’t want to force you to do anything. I’m thinking of myself right now as like the consultant to your CEO. So tell me: what do you want?

Dana (45:16)

Okay. I think I like the one-night idea without the pressure of it having to be a date. So, like, you know, I’ve set goals for myself where I’m like, I have to go on one date a week, and I have to go on a dating app every night. So I would put it on my phone, and then most nights just not do it. So I think one night a week just to prioritize dating—whether that’s myself or IRL—is doable.

Lily Womble (45:56)

Good, good. Why did you avoid getting on the dating app?

Dana (46:04)

Other things to do.

Lily Womble (46:06)

Yeah, sure. We’ve talked about how it felt like your perception of the wrong people really slowed you down.

Dana (46:14)

Yeah.

Lily Womble (46:14)

How do you think our conversation might impact how you interact with the dating app differently?

Dana (46:22)

I think the vetting process too. I feel like earlier this year I vetted everyone and was like, nope, nope, nope, nope, nope. But really having more intentional early conversations—yeah.

Lily Womble (46:38)

Yes. Can I see your dating app profile? Do you have it?

Dana (46:43)

I—

Lily Womble (46:45)

Okay, for everybody listening or watching on YouTube, I have Dana’s profile now pulled up in front of me. Let’s talk about your profile, Dana, to make it reflect your essence-based preferences.

Dana (46:55)

Okay.

Lily Womble (46:56)

Okay, so this is why it’s important to start with preferences, because everything builds on itself. So you start with preferences, then you figure out what vetting questions you need to ask. Then, how I do it with my clients inside Main Character Dating is they answer all of their own questions. Like, “What’s bringing you joy lately?” Have you answer that. And then that data becomes great stuff for your prompts—to make them intentional and really direct.

Dana (47:15)

Yeah. Yeah, love it. Okay, cool.

Lily Womble (47:27)

Okay, so I think your pictures look so great. I do want a picture with you more chest-up. I love the full body, I love the adventurous, but I want one of just seeing you. Yeah—like a headshot, but not stiff. Get a friend of yours, go on a friend photoshoot, and at brunch or on a walk, have them take a hundred photos of you.

Dana (47:40)

Okay. Okay, like headshot. And—okay.

Lily Womble (47:58)

Smiling, in a joyful moment ideally—and that’ll be great. So: “One thing you should know about me.” Can you read this to me? Because in the screenshot I see a little ellipses, I don’t see the full thing. So read to me what you have.

Dana (48:01)

Okay. I see—this is so, I need to update this—but it says: One thing you should know about me: I have a high-pressure job during the work week. With that said, one of my life mottoes is work hard, play harder.

Lily Womble (48:25)

Okay, so we need this to be more intentional. Everything in your profile is really valuable real estate. And so I think that one thing—you don’t have to choose this prompt specifically. Are you on Hinge or Bumble? I can’t really tell.

Dana (48:31)

Yeah. And this is Mitch.

Lily Womble (48:41)

So “one thing you should…”—let’s just keep this one for the sake of going through it and figuring out your best next steps. I think that “One thing you should know about me” should be about: I am an adventure traveler—

Dana (49:01)

Okay.

Lily Womble (49:01)

—who deeply cares about my patients, if you want to talk about that. Like, I am an adventure traveler who cares deeply about my patients and their wellbeing.

Dana (49:04)

Thank—yeah.

Lily Womble (49:15)

I’m really passionate about—and you could even say: I’m an adventure traveler passionate about climate change, caring for my patients, and being really silly in an improv class. Do you see how different that is? Because you were starting with: “Sorry, I have a high-pressure job. Sorry, I’m busy.” When it’s like—okay, you’re busy.

Dana (49:27)

Yeah, yeah.

Yeah. Yeah.

Lily Womble (49:44)

You have a high-pressure job. Great. What’s great about it? Why do you love it? What’s what? And I’m not saying that has to be your final answer, but we don’t need to start with an apology.

Dana (49:53)

Yeah, yeah, I like that.

Lily Womble (49:55)

Yeah. So I think that the energy that you bring to your profile is important because it can qualify and disqualify people. And sure, people aren’t as truthful about their profile or whatever. You’re going to snuff that out with your qualifying, disqualifying questions. Or on a first date, if someone’s not right for you, you’ll be able to bless and release more unbothered because of this new energy. Okay. Try to guess this about me: which of the seven continents I have not been to. Okay. This is getting to the adventure traveler piece, but I don’t think it’s a valuable use of real estate.

Dana (50:08)

Uh huh. Uh huh. Okay. Got it. Delete.

Lily Womble (50:26)

Because it’s not inviting dialogue, it’s like, “play this game with me,” and I want it to say more about you.

Dana (50:32)

Got it. Right. Okay.

Lily Womble (50:38)

Here are my favorite Hinge prompts. Here are my favorites:

• This year I really want to.
  
• My simple pleasures.
  
• Typical Sunday.
  
• My friends ask me for advice about.
  
• I feel most supported when.
  
• To me, relaxation is.
  
• If loving this is wrong, I don’t wanna be right.
  
• The key to my heart is.
  
• My favorite favorite is: I won’t shut up about.
  

Dana (50:45)

So cool.

Lily Womble (51:04)

Because that gives you a chance to really let yourself out. Together we could…

Dana (51:06)

Yeah, yeah. Okay, all good ones. I have to think about these, but yeah.

Lily Womble (51:16)

To me, relaxation is would be a really great one for you because that would qualify/disqualify someone who has a different view of relaxation. You could say like,

Dana (51:22)

Mm-hmm.

Lily Womble (51:28)

For me, it’s finding a hammock in a beautiful place and then going on a 10-mile run or something like that to really showcase that you are about an adventurous, very, very active lifestyle. And that you are a nine—you’re a nine out of 10 looking for a six out of 10.

Like, that’s not something I would say on your profile, but we need to exemplify that in how you answer these questions. So I put my favorites—the ones that I just read out—in the chat for you. But I mean, this is just the beginning. We just used that first one, “one thing you should know about me,” and I shifted your approach. I think we should change the prompt “try to guess about me” to something like “the key to my heart is,” or “I won’t shut up about.” So an example of a great…

Dana (51:45)

Love it. Right. Right.

Lily Womble (52:13)

“I won’t shut up about” is my client who said, I won’t shut up about the Washington Spirit, their championship run, their ownership battle, the awesomeness of women’s soccer, and the talent of the players. Looking forward to seeing them in action at Audi Field this year.

So it showcases her passion, that she travels for her passions, that she cares about women’s soccer, showcases her values. Here’s another example:

“We’ll get along if… you seek personal growth, are serious and playful, have integrity. You take care of yourself and know your way around your emotions. Practicing yoga is a plus.”

Dana (52:54)

That. Wow, good.

Lily Womble (52:56)

Do you see how different this is?

Dana (52:58)

Yeah. Yeah.

Lily Womble (53:00)

And then your final prompt that you shared: I’ll brag about you to my friends if you have a sense of humor, can give a killer massage. What else did you say? Because it’s got a little ellipsis.

Dana (53:10)

Let’s see. Have passions and hobbies that align with my own. You are not afraid of vulnerability, international travel, and epic adventures.

Lily Womble (53:25)

That’s a great start. I think that like, I’ll brag about you to my friends if… you love cultural immersion, travel with cultural immersion, you are game to like go to an improv class. If that matters to you—it doesn’t have to. You have an amazing friend group of your own.

Dana (53:35)

Okay. Mm-hmm.

Lily Womble (53:50)

And you go to therapy, right? Like, you could say that in your profile.

Dana (53:54)

Yeah.

Lily Womble (53:55)

And then something that I love encouraging folks to add to their profile is I’m looking for… Saying something like, Looking for a partner to live fully with side by side, then hopefully we go scuba diving on six continents. Something like that.

Dana (54:08)

Huh.

Lily Womble (54:11)

So I think after you make those shifts, you will have a more robust profile that’s more you. And that’s going to be really important for your confidence and feeling authentic and feeling like, “I’m putting it out there.” And then in terms of like the fear of “I have less experience,” I mean, role playing that just goes with the right people. It’s like, “Tell me more about that.”

Dana (54:21)

Yeah.

Lily Womble (54:37)

With the wrong people, they’re going to be like, “That’s weird,” which is an immediate disqualifier.

Dana (54:40)

Yeah. Right. Do you think—so someone actually, another coach at one point, said I should hint to that inexperience in sort of a different way, but to put that on my profile and ask, like hint, like, “Is this something you’re okay with?” Or no, don’t? Okay.

Lily Womble (54:59)

No, no, I disagree. I disagree. I think that’s the least interesting thing about you. Why would you put it on your profile, right? It’s not—it’s like, don’t. Like, if you really wanted to, we’d figure out a way to do it. But I don’t—don’t. It’s not something that is a disqualifier for the right people. It’s like, if you had a kid—

Dana (55:07)

Bye. I don’t really want to. Yeah.

Lily Womble (55:25)

I would say that’s a different story. Let’s put your kid on your—let’s mention somewhere that you’re a single mom. But it’s not like this is—I mean, this is just a temporary circumstance. Like, when you meet somebody, you’re looking for an emotional/physical connection. You’re not looking for a perfect match in level of experience.

Dana (55:30)

Yeah, no. Okay, I like that answer.

Lily Womble (55:51)

Yeah, don’t worry about it. Because I think that person was saying that more like, “Well, you want to protect yourself because some people wouldn’t be okay with that.” Well, then they would be disqualified.

Dana (56:01)

Mm-hmm. Yeah. Good. Okay. Awesome. Yay. Thanks, Lily.

Lily Womble (56:06)

Yeah, I’m excited for you. Then IRL—we are at the end of our time, we could talk literally for five more hours. This is why I love coaching on this. But I want you to set up an intentional dating app practice that is like 10 minutes every other day or something like that with one dating app. And I want you to celebrate your wins more and bring more collective belonging to this area of your life by texting a friend, “Hey, I’m intentionally—

Dana (56:15)

Hahaha. Okay.

Lily Womble (56:36)

—trying dating in a new way.” And open with your “what’s bringing you joy?” question. And then in the conversation, have a cutoff point of like after five days, I either ask them out and then we need to co-create a date. They need to be equally interested. Or I bless and release. But set a cutoff point. It could be five days, could be four days, could be 10 days. But just know for yourself, what’s your boundary?

Dana (56:38)

Mm-hmm. I love it. Bye. And.

Lily Womble (57:02)

So that you can be more prepared to cut it off when somebody’s a pen pal or not right for you. And you can also shoot your shot. And then if they say yes, their job is to help you co-create a date.

Dana (57:03)

Yeah. Yeah. Yeah, love it, love it. I can’t wait to re-listen to this because I’m trying not to take too many notes.

Lily Womble (57:20)

Well, it’s going to be so, so exciting to step into this new era of your love life. And also, sometimes it’ll feel like, “Oh, I backslid,” or “The dating app still sucks.” The dating app is not changing. You are changing—the way you set boundaries, the way you ask for what you want, the way you show up for what you want. And this is just one expression of showing up for what you want. In-person dating, joy building, asking a friend to help you, educating co-conspirators, and making eye contact in the wild.

Dana (57:40)

Yes.

Lily Womble (57:50)

And you have chapter eight, chapter seven of the Thank You More Please book to help you with that strategy or my podcast episodes.

Dana (57:57)

Awesome. Cool.

Lily Womble (58:00)

Well, thank you, Dana, so much. This was so, so fun to work with you and I can’t wait to hear your update.

Dana (58:02)

Thank you. I know, it’s amazing. Thank you so much. I’m so honored to meet you in real life. You’re exactly how you portray yourself in your book and your podcast. You’re amazing.

Lily Womble (58:12)

It’s so nice to meet you. Same back at you, and we’ll talk soon.

Lily Womble (58:24)

Thank you, Dana, for coming on the podcast to talk with me and thank you for your willingness to be vulnerable and to be coached. It was an honor coaching you. I had a blast and I hope that you feel more powerful in this process. I hope that you know that what you want is even more possible than you realized. And I am so excited for this new main-character-energy chapter of your love life.

Dana sent us a video updating us after this session on how she felt, what changes she implemented. So let’s get into that update.

Thanks again, Dana, and I want you all listening to go out and make one intentional change for your love life because you get to re-center yourself and your desires starting right now, and that will make you more magnetic toward the right opportunities and right people for you. You’ve got this, and I’ve got your back. Talk to you next week.