In this kickoff to the Late Bloomer Series, Lily gets real about how to tell a date you’ve never been in a relationship—without spiraling, oversharing, or self-abandoning. If you’ve ever felt behind in love, this episode will help you embrace your story, communicate with confidence, and stop making your dating history mean something it doesn’t.

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Show transcript:

Lily @ Date Brazen (00:00.259)

Hey, gorgeous friends. Welcome to another episode of the Date Brazen podcast. I’m so glad that you’re here. Today kicks off my brand new series for the podcast called the Late Bloomer series, all about your most frequently asked questions and worries and doubts about being a late bloomer in your dating life. This series is going to eliminate so much of your self doubt, so much of your spiraling thinking and rumination, just gonna give you very clear action steps.

to overcome some of the most common questions and worries that I hear every single day from late bloomers. Because I was a late bloomer. I was somebody who did not have much dating experience. I came from the deep South where I was taught that a woman should be less, that I was too much, too sensitive, too bossy, too intense. I had a high school boyfriend who I was like deeply, deeply in love with.

and also didn’t have much physical experience because I was very much in the evangelical Christian love weights community. So when that boyfriend broke up with me, literally telling me you’re too much, I can’t make this stuff up, I went into adulthood really feeling like I needed to shrink myself in order to belong, that I needed to make my wants and needs less in order to attract a romantic partner.

And I entered adulthood not really knowing how to date. I was deconstructing my love weights background. I was kind of ready to have sex, ready to get it in, ready, but didn’t know how to do it at all. Didn’t know how to date, didn’t know how to ask for what I wanted, didn’t know how to tell people that I had never been in an adult relationship, didn’t know how to tell people I had never had sex before.

I was dating in San Francisco and New York at the time in my 20s and it felt like so shameful to have not had a quote adult relationship before. I felt like a total late bloomer and my overthinking and anxiety about what do I say? When do I say it? It’s gonna freak them out. They’re gonna run away. This is another reason why it’s not gonna work out for me, right? All of that was like so paralyzing.

Lily @ Date Brazen (02:18.736)

And I know for some of you, you might be listening to that and you’re like, Lily, I’m living that in my 30s or 40s or 50s, what have you, your 20s, LOL, I’m over here still in my whatever age dealing with this. I just want you to know you’re not alone. I want you to know that I coach people every single day inside of my program, Main Character Dating on this exact topic of how to find love as a late bloomer. I did it with these tools that I’m gonna share with you in the Late Bloomer series.

Went from feeling a Gallate Bloomer so anxious and so much overthinking, so much rumination, so much worry all the time, and shrinking to feeling confident in who I was and what I wanted, feeling emotionally safe enough to take risks, to put myself out there to shoot my shot, even if it meant being rejected, I was emotionally safe enough to take risks and I celebrated myself along the way. I felt free, I was giving my number to cuties.

I remember I gave my number after doing this work for myself to a waiter and I went on a date. The skillset that I’m going to teach you in these episodes for the Late Bloomer series, the skillsets that I teach you in this podcast, in my book, Thank You More Please, A Feminist’s Guide to Breaking Dumb Dating Rules and Finding Love available now. Literally everywhere all books are sold. Those skillsets are exactly what have helped not only me, but

Hundreds of clients come home to themselves, own what they want and find it, attract it with more joy than they thought possible, or confidence than they thought available to them. So that’s why I’m so excited to invite you into this warm buttery series of the Late Bloomer series. Today we’re starting off with a bang. The subject, how to tell somebody that you’ve never been in a relationship. Let’s get into it.

Hey, I’m Lily Wonville, former top matchmaker and founder of Date Brazen. After setting up hundreds, I realized that with coaching, women could match themselves better than anyone else ever could. With my unconventional feminist approach, I’ve helped women around the world build courageous and self-trust-filled love lives, and now I’m here to support you. Get ready, because I’m about to share the exact steps you need to attract a soul-quenching partnership and feel amazing about yourself along the way. This is the Date Brazen podcast.

Lily @ Date Brazen (04:44.248)

I am so excited to announce the sponsor of this episode is my free guide to creating your essence-based preferences. This is a free 14-page workbook that I have created for you to really give yourself permission to want everything that you want, to stop worrying about being too picky, there’s no such thing, and to discover how you want to feel in the right relationship. This free essence-based preferences guide will help you cast the vision for your future partnership.

It’s not a rigid checklist and it’s not an open-minded pile of mush, especially if you’re a late bloomer. It’s gonna ask you the right questions to help you get to the bottom of what it feels like to be in the right relationship. Again, even if you’ve never been in a relationship, this guide will help you get clarity on what you want and how to communicate what you want out loud and often. Essence-based preferences are one of the core skills.

that my clients who find the best relationships of their lives regularly say is how they knew that person was their person. Like pretty quickly after meeting them. Essence-based preferences are a subtle proofing force. They’re gonna help you get to know not only what you want, but how to vet for it. Once you know what you want, once you have this vocabulary for your love life, you can start vetting for it. And after every single date.

Tune in with your intuition using that rubric. It’s just gonna clear up so much of the overthinking and confusion that so many people face in dating. Essence-based preferences are your living, breathing documentation of your desires. It’s how you wanna feel in the right relationship. What turns you on and makes you come alive across the table. It is also going to help you be open to being surprised by the package the right people or person comes in.

Because a rigid checklist is sort of like a wall going up. Must be this height exactly, this location exactly, this job exactly, X, Y, Z. That is keeping you from being surprised by the right person. On the other end, we have people who are taking their hand completely off the wheel saying, I just want somebody nice with a job. In which case you’re not wanting enough. Coming in the middle with essence-based preferences is going to allow you to be open to being surprised by the right person while still holding your preferences and boundaries.

Lily @ Date Brazen (07:03.684)

while still being powerfully picky. So go to the link in the description of this episode or go to datebrazen.com slash workbook to get your hands on this free 14 page guide. I cannot wait to hear what your essence based preferences are. And it’s a great thing to do with your friends on a Friday night. It’s sort of like a vision boarding session for your future relationship. And again, it’s totally free. So go get your hands on that guide. And with that, let’s get back into the episode. Okay.

Late bloomers. I define late bloomer as anybody that feels behind in their dating life. So if that’s you, listen up, whether you have never been in a relationship or you’ve been in one a long time ago and you’re embarrassed at how long ago it was, or you just got out of a 20 year marriage and you’re embarrassed about not having dated before or whatever. If you feel behind in your dating life, this is for you. You are afraid of being asked, when was your last relationship on a date?

because you’re afraid that your answer will be a deal breaker to people. And underneath that assumption and fear is just the general desire to be safe. The general desire not to be rejected because humans fear rejection like we fear death because neurobiologically that makes sense. When we lived in caves, being rejected meant being put out of the cave and dying of exposure. So it makes total sense why you have this fear of rejection. Also, you have a desire because you’re listening to this podcast.

You want to find the right relationship and you’re afraid that it doesn’t exist for you. And so if you go on a date, you know, for some of you who feel like late bloomers, it’s like, God, if I, if I could find a date or if I had the courage to get on a dating app or just start dating, if I could just get on a date, okay, you’re on the date. Then you think about being asked, so when was your last relationship? And you’re afraid that you’re going to say the wrong string of words or that any string of words won’t be enough.

for the person sitting across from you. And that inevitably it’s gonna lead to them saying like, gross, weird, that’s so weird of you. What’s wrong with you that you haven’t been in a relationship in X number of years or ever, what’s wrong with you? And then you’re afraid that that person’s reaction means and will affirm your fear that you’re just gonna die alone. Am I hitting something here for you? Is this resonating? I think if you

Lily @ Date Brazen (09:29.26)

are listening to this, it probably does resonate at some level, right? You’re afraid of the confirmation that your worst fear is like alive and well, that your lack of relationship history is weird and a turnoff and a deal breaker for everyone, right? I’m gonna tell you something. You need to stop centering the people who are wrong for you in whether or not you believe yourself.

I’m going to say that again. You need to stop centering the people who are wrong for you in whether or not you believe yourself. Not trying to date because of a fear of someone else’s opinion. While understandable, you want to be safe. Not dating for fear of their rejection or opinion is centering them and their one person opinion in whether or not you believe in your own desire for the right relationship. How do you find the right relationship?

You practice dating messily with self-compassion. Period. The way that you find the right relationship is by giving yourself permission and want what you want, trusting yourself, hopefully building that skill of self-trust so you know like, I’ve got my back no matter what. And then just doing it messy, doing massive messy action. That is how you find the right relationship. It’s not a deal breaker that you haven’t been in a relationship before. It’s not that deep.

Now I hear you saying, you’re wrong, Lily. People have thought I was weird. And those were the wrong people for you.

So hard to internalize, but so true. Those people were the wrong people for you. Okay? Stop centering the wrong people for you and whether or not you believe what you want is possible. It’s the same fear that comes up for most people around anything. Yeah. So you’re not abnormal for having this fear that you’re going to say the wrong thing or that you have the wrong history to find a relationship. Everybody has this fear at some level about something in their life, right? Whether it’s about, you know,

Lily @ Date Brazen (11:36.122)

the whether or not they want a family, whether or not they want to be child free, whether or not they want to pick up their life and move across the world. And they’re afraid that the person they speak to is going to not want that. so they’re not going to try to date because everybody’s got fears. And something that I think is really tough for folks who identify as late bloomers and why I love my job so much is because the anxiety and loneliness present and isolation present.

for people who identify as late bloomers is so fucking high. And it’s exacerbated by silence. And a lot of late bloomers choose to stay silent, choose to not talk about their dating lives with friends even, because they’re afraid of their worst fears being confirmed. And they’re afraid that they are weird, that they haven’t been in a relationship, that it’s never going to happen. They’re afraid of their friend’s judgment, or they’re afraid of a date’s judgment. So they stay silent and then isolation continues. And then…

Maybe shame is present, right? And it just becomes a hot soup of loneliness and exhaustion. So I’m here to tell you that this is figure-outable, that you’re really not alone, that your relationship history is not a deal breaker to finding the right relationship. Your lack of relationship history is not a deal breaker to finding the right relationship. People who were late bloomers find love every single day. I was one of them.

I know many of my clients who were late bloomers who were afraid that what they wanted wasn’t possible. let’s just, I just want to level set with that normalizing, right? Hopefully it feels like a big old quilt that we’re laying over all of our laps together. You are normal. You’re in the right place. This is figure edible. Now let’s get down to the how. Okay. So the how of it all, there are a couple of like things that people do that I think you should stop doing if you’re

doing them, okay? One is avoiding dating altogether because you’re afraid of somebody’s reaction. I want you to start owning what you want and going after it. This is our one wild and precious life, in the words of Mary Oliver, and you’re not dead yet. I think that’s a piece that a lot of people are forgetting. This is our one wild and precious life and you’re not dead yet. So why not try something new? Yeah? Why not try something new? You don’t know everything yet. You probably are a high achiever. You’re probably super ambitious. You’re probably convinced that you do know everything yet you don’t.

Lily @ Date Brazen (14:01.264)

Okay? It’s possible for you to learn something new. It’s possible for you to meet someone new. It’s possible for you to learn a new skill, AKA why you’re here, to learn how to tell somebody that you haven’t been in a relationship yet. Another thing that people are doing that I think you need to stop if you’re doing it is over explaining. Yeah? So you don’t owe anyone your story, period. You don’t owe anyone your story. And I think I’ve seen so many people…

who when asked, because we do this role playing thing inside of main character dating sometimes, where we role play this conversation, I’ve done it several times in this community, it always is so fascinating and also ends up being so empowering for folks. Because when you practice the worst case scenario, generally it’s like, why haven’t you been in a relationship? And then they say, because…

I really was, I don’t know, ha ha, they make a joke of it or they start over explaining and telling all of the details. by the way, when my clients share the details of why they haven’t been dating, tales of paralyzing fear, tales of caregiving for a parent for decades or a friend for decades or a sibling for decades and not having any time for themselves and just not learning that skill of dating.

or whatever, I’m always so understanding. I’m always like, it makes sense. Why you haven’t dated, it makes sense why you haven’t found a relationship yet. It’s not a personality flaw. It’s not that you’re so repulsive that nobody wanted to be with you. It’s just a life circumstance that you haven’t dated yet. So.

So I’m always so understanding and I just think about if I exist, then I know there are people that exist like me out there who will also be understanding, especially those who are on a date with you. So I don’t think you need to over explain for someone to empathize with you. You don’t owe anyone your story and I don’t want you to over explain yourself out of fear that over explaining will lead to a better outcome. It probably won’t in a date scenario.

Lily @ Date Brazen (16:08.196)

But when a client is telling me this and they’re nervous and we’re role playing, I’m always like, totally get it. I pause the role play. like, first of all, I totally get it. Makes total sense. And back in the role play, in the role play scenario, I then give sort of the worst case scenario. Like that’s super weird. Like why that, that, that feels like a, like a flimsy excuse or whatever. And then I get inevitably like a feeling of disgust in my body. I stopped the role play again. I say,

Who is that person who would say that to you? A jerk, not a person that you would value their opinion, huh? On many other things, huh? Why are you letting the fear of their judgment and opinion drive you and your actions? You powerful badass. But I digress. So I don’t want you to over explain. I want you to just stand in your truth, own your space. You don’t owe anyone your story.

when you have established trust in a relationship, in a new relationship, sure, share your story in more detail. Talk about your story in more detail. But when we’re talking about a first, second, third date, you don’t owe anyone anything. Here is how to answer the question succinctly and powerfully, to own your space, to own your story, and to move on. Somebody asks you, so when was your last relationship?

your brain’s going to be freaking out, freaking out, freaking out. But luckily we’re practicing right now. I want you to say the words out loud after I say them to practice whatever resonates. Okay. And save this episode to listen to again and again, if you need to take notes, whatever. All good. Do what you need to do to learn this skill of standing in your truth, standing in your power, answering open and honestly, because I don’t want this to stop you from trying to date. Back to the question. So have you dated much? When was your last relationship?

Actually, I haven’t dated very much. I’m reprioritizing dating in my life, trying to find the right person and excited to make new connections. That’s enough. You don’t have to be like, actually, I’ve never been in a relationship before and this is my first date ever and I’m really nervous and I hope it’s going well and I hope you like me and I hope that I don’t burn out and stop dating like I did five years ago when I tried this last time, but at least I got in the door this time.

Lily @ Date Brazen (18:29.633)

And I got in the door this time and maybe that’s a success.

Lily @ Date Brazen (18:37.326)

You know what? I’m reprioritizing dating in my life right now. I’m excited to find the right people, excited to have some fun connections. And I haven’t dated very much, but I’m excited to be here now, period. And then what if they follow up? Lily, what if they follow up with, when was your last relationship though? They could ask, they could be curious. They might want to talk about their own past relationship, whatever. You could just say, I honestly haven’t had that many relationships.

had prioritized other things in my life and now dating intentionally is the priority. I have, I’m going to repeat it so you can repeat it after me. You know what? haven’t had a relationship because I haven’t prioritized dating before now, but now I’m really dating intentionally and feeling good about it. Now I’m really dating intentionally and excited to make connections. The more you can practice that out loud and unclench your butthole while you do.

and take deep breaths, the more prepared you will be in that scenario. watch for their reaction. So there’s two things here. There’s your nervous system and your response, your fear of what their response could be and navigating that and being compassionate towards yourself. Self-compassion says, of course I’m freaking out about this, makes total sense. I’m just afraid of the outcome that’s really normal. And I’m here with you. I’m not alone. Offer that to yourself.

So there’s the you part, which is very clear. You’re in charge of how you treat yourself, how you talk to yourself. You are in charge of how you respond. You are in charge of how you allow yourself to hold firm in your power and like own your story, but not over explain because you don’t owe anyone your story. And then there’s the, what are they going to say? Right. And what am I going to do if they say something or another? Maybe they’ll say,

Okay, that’s weird. Okay. In which case their reaction would be information. Information like here’s how I would want somebody to respond to me. And here’s how people did respond to me on some dates. They would lean and be like, that’s interesting. You know, you’re so great. Why didn’t you date very much? I just didn’t. You know, I was prioritizing other things. I lived in the South. I didn’t really vibe with any of the people around me.

Lily @ Date Brazen (21:03.524)

What about you? When was your last relationship? Right? That’s one version of a response. Another version is sort of the like, weird. You’re so weird. Bless and release. Yeah. You can practice after that conversation, going to the bathroom, taking three deep breaths, deciding to come out and be like, you know what? I’m done. I hope you have a good night. You can do that. All of this is made up. Okay. Alternatively, they could just be curious and like lean in. That’s a

qualifying response. You’re looking for a qualifying response, not a disqualifying response. And if they’re genuine, if they’re curious, then you can answer in so far as you want to. And if they ask a question that you don’t want to answer, you can always say, I don’t really feel like talking about that, or I don’t feel comfortable talking about that on a first date or whatever. You can always say that, but this level of communication will require you to be uncomfortable.

This level of communication will require you to allow an awkward silence. This level of communication is asking you to stand in your main character energy instead of shrinking. And that’s gonna be scary at first. So that’s okay. You can learn new things anytime you want to with practice, with imperfect practice. Be willing to be bad at this first. Be willing to stumble over your words a little bit and not know exactly what to say.

practice. So remember, their response is information about them. And if you do experience a rejection or a heartbreak after having this conversation, that’s really tough. And with the skills I teach you in this podcast, with the skills I teach in my book, thank you more, please, with the skills of self compassion, all of those tools are what you can call upon to move through the post date vulnerability hangover, because you will have one.

No matter what the response, I think you’re going to have one. And I want you to know that for the right person, they’re going to be curious, not judgmental. For the right person, they’re going to say, tell me more. Or they’ll ask another question. With the right people, they’re going to be curious, not judgmental. Because why? The right person also wants to be with you. And if you want, can prepare for this date conversation for the future with the four step communication guide that I wrote about in my book.

Lily @ Date Brazen (23:23.634)

adapted from the work of Jameson and Gower from their book, Radical Alignment. Radical Alignment has this great communication framework tool in it where you name four things. Your intention, so my intention is to respond to the question, when was your last relationship? And after your intention, you claim your concerns. What am I concerned will happen? What’s my worst case scenario? You write down, they leave or they judge me or they are mean.

Then you write out your boundaries. What is your plan when and if a worst case scenario thing happens? When and if a concern happens? Four, what’s the best case scenario? What are your dreams? What could happen with the right person? If you prepare with that list, you’ll be fine and you’ll be more prepared to enter a date and to have a conversation that is deep and that you might be asked, when was your last relationship in? And that you’re gonna be fine in. The right person is looking at you saying,

I hope they like me. The right person is looking at you saying, I feel really lucky I’m on a date with them. The right person might be like, I can’t believe they’ve dated, not dated before because they’re so fucking great. The right person for you is gonna feel lucky to be with you, period. You are uniquely qualified for the love of your life. And I know this because I’ve seen it happen hundreds of times. Think about when you made a new friendship and it was a really fun new friendship and you became really, really close. How lucky you felt to be their friend and how-

Lucky they felt to be your friend. The same is possible for romantic connections as well. You just have to be willing to try something new and be uncomfortable in the pursuit of your main character energy and in the pursuit of your desires. That is episode one of our Late Bloomer series. I am so excited for you to put this into practice. I really want you to write yourself a big old permission slip. I have permission to take up space on a date. I have permission to not over explain. I have permission.

to share this sentence. And if I want to share more, can, but I don’t have to. I have permission to do this on my terms. And then use this episode to maybe even role play with a friend. Talk to them about your concern, your fear about saying this on a date and bring up this conversation. Maybe do one version where it’s like worst case scenario and then take a deep breath together, maybe hug, and then do one version where the person is just really your kind of person, generous, kind, curious.

Lily @ Date Brazen (25:46.931)

and it’ll help you to get it in your bones. Like, you know, I haven’t had many experiences or haven’t had a romantic relationship and I’m really prioritizing dating now, excited to find the right connections, period. You’ve got this and I’ve got your back. Go download that guide to creating your essence-based preferences at datebrazen.com slash workbook so that you can start to build your love life vocabulary, start to cast the vision.

for this amazing, curious, kind, generous partner that you are magnetizing to you just by claiming what you want and taking up more space in your love life. So go download that guide. I cannot wait to hear about your essence-based preferences. I cannot wait to hear about how these conversations go. You’ve got this and I’ve got your back. Talk to you next week. Thanks for listening to the Date Brazen podcast. If you liked this episode, then you’re gonna freaking love my book. Thank you more please. It’s my proven step-by-step feminist guide

to breaking dumb dating rules and finding love. You can buy it anywhere books are sold and then get a juicy bonus at datefrazen.com slash book. The bonus is the dating life fix. My top 10 podcast episodes to get unstuck right now. And be sure to subscribe so you never miss an episode. You’ve got this and I’ve got your back.