Ever catch yourself thinking: “Why would they like me? What’s wrong with them for wanting me?”

This sneaky belief keeps so many late bloomers stuck in self-doubt, playing small, and avoiding the very love they crave.

In this episode, Lily gets personal about how this thought showed up in her own love life—even when she met her now-husband—and shares the powerful mindset shifts and tools you need to bust through this myth for good.

Inside:

✨ Why this belief is so common for late bloomers
✨ How it blocks you from trusting healthy connection
✨ The ACK tool to start rewiring your brain for worthiness
✨ Real-life reframes to help you believe, “Of course they like me!”

Listen now and start stepping into your main character energy—for love, dating, and beyond.

Work with Lily:

Learn about her signature program, Main Character Dating: datebrazen.com/waitlist

Book: Thank You More Please

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Show transcript:

Lily @ Date Brazen (00:00.409)

Hey gorgeous friends, welcome to another episode of the Date Brazen podcast. I’m so glad that you’re here. Today, I’m going to be busting through one of the biggest myths that you as a badass late bloomer probably believe, or maybe you sneakily believe under the surface, which is this thought that I don’t trust anybody who would want to be a part of my team, AKA, if they’re into me, what’s wrong with them? Okay, it’s a very common story for people who feel behind in their dating lives.

I felt this story, I believed this story. In fact, when I started dating my husband, Chris, I internally had the thought like, what’s wrong with him that he’s into me? Because I, because of some childhood wounds, because of some bullying that I experienced as a kid, because of growing up being told that I was too much, too sensitive, too bossy, too intense. And then after not receiving much romantic affection or interest for much of my…

you know, like young adulthood, high school into college into young adulthood living in San Francisco and then New York, I didn’t receive very much romantic attention. And so I internalized that lack of attention and really believed that something was wrong with me and that I was broken and that I needed to make myself smaller or shrink or fix myself in order to be attractive. So when I met Chris, it was a real shock to my system.

because he liked me, he felt like safe and he felt like exciting and attractive to me. And I was immediately, I mean, in addition to being kind of gooey and falling for him, I also had this thought underneath the surface, like there must be something wrong with him. I’m waiting for the other shoe to drop because someone like this can’t be into me. And so in this episode, we’re gonna uncover this belief. We’re going to untangle it together and I’m gonna offer you an alternative.

so that you can actually believe your worthiness and start attracting better dates than you thought possible while knowing that you’re worthy of them. So let’s get into it.

Lily @ Date Brazen (02:10.896)

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. Here’s how to heal this pattern of believing.

that why would they be into me or there must be something wrong with them because they’re into me. To heal this pattern because it’s keeping you stuck, it’s keeping you doubting yourself, doubting your desires, playing smaller than you need to and it’s sexy summer, okay? I am in just pulling back the curtain. I’m in my room where I record these podcast episodes. If you’re watching me on YouTube, you may see me like start to glisten. That’s because it’s summer in New York City and to record these podcast episodes, I turn off my AC.

Okay, first to heal this pattern, you gotta name it. Okay, we’re gonna use my tool, AK, that I’ve talked about in previous episodes to start to name and heal this pattern of you playing smaller than you need to. And side note, you might have experienced people being into you in your past that you’re not into. And you might have internalized that as see, that’s evidence that people that I’m into aren’t into me and their quote must be something wrong with somebody if they’re into me, I must not be attracted or they must not be.

a personality fit or whatever. And I’m gonna urge you to not make that mean anything other than you’ve met people who are into you who you weren’t into. It doesn’t have to be that deep. It doesn’t have to mean everything about what’s possible for you and your love life. And so I urge you in this episode to be really aware of the stories that you’re making up based on your past experience and how confirmation bias, AKA it’s never gonna happen. So your brain searches for evidence to prove that story.

right in order to be safe. See how confirmation bias might have been creeping in to your love story, to your love life. That’s why I see so many late bloomers getting a cycle of burnout, self-doubt, stopping dating altogether, which is fine. Nothing wrong with being single. In fact, singleness is amazing. You get to be single if you want to be single. And if you want to find the right partner, you get to do that also with more self-confidence, with less self-doubt. And that’s why this episode is here.

Lily @ Date Brazen (04:37.02)

So let’s go back to ACK. I’m gonna say it again memorably so that you capture it and hold onto it and put in your little pocket. ACK, acknowledge, compassion, kind reframe. First you gotta acknowledge, hey, I’m having this thought that if someone’s into me, then there must be something wrong with them. If you’re having that thought, if you’ve struggled with that in the past, or maybe it’s nobody that I’m into is gonna be into me. A lot of my clients feel like they’re cursed quote unquote,

They haven’t experienced mutual attraction before with somebody. They’ve been attracted to people who haven’t been into them, people who have been into them, who they haven’t been into. So I just want you to acknowledge, stop and acknowledge, okay, my brain is having this thought, okay? The thought then creates the feeling in your body. Maybe the thought is nobody that I’m into is into me. And then the feeling that you have is maybe some despair or anxiety.

maybe even shame, yeah? So the thought then sparks the feeling that then sparks the actions. This is basically the model by Brooke Castillo. I didn’t get trained in this coaching school, but I find this tool really helpful just to like, again, put in your pocket to understand your thought then sparks a feeling that then sparks actions. Like if you’re having thought, nobody that I’m into is into me.

and then you’re having the feeling of shame or despair or anxiety, then the actions that you take from that place might be hustling more, proving your worth, going out with people that you’re not into, or it might be under-functioning, like laying on your couch and stopping all dating altogether, even though you have this deep desire for the right partner, you are like shrinking and going into your safe hidey hole, which again, there’s a time and space for that level of healing and self-protection, both and when you’re ready, I want you to.

putting yourself out there. But that thought, nobody that I’m into is into me, or what’s wrong with them that they’re into me, creating the hard feeling, creating actions that are not moving you forward, and it’s creating the results of you don’t get what you want this summer or ever. Yeah? Because what you want is on the other side of main character energy and trying, like giving yourself permission to try, learning how to trust yourself as you try, then taking massive, messy action to try new things.

Lily @ Date Brazen (06:55.547)

to meet new people, to make new connections, to believe that you are worthy of what you want. So that is maybe what your brain is doing now. So I just want you to acknowledge it. It’s like diagramming a sentence, like looking at how my brain might be interpreting the circumstance of I’m feel, I haven’t been on many dates or I haven’t been in many relationships. Acknowledge it, acknowledge the thought, acknowledge the current state of affairs in your brain. That’s number one. Number two, compassion.

Let me talk about it again and again and again. It’s not going away. This the practice of self compassion is three things as defined by Dr. Kristin Neff. Mindfulness over over identification. So even acknowledging the thought that you’re having is a thought not a fact is self compassionate. Community over isolation. I’m not alone. This is really normal to struggle with feeling behind in my dating life or feeling shame about being behind in my dating life or you know not trusting.

that people will be into me. That’s a human experience. There may be nothing wrong with me except that I’m having some thoughts. That’s not a bad thing. It’s just human of me. How human of me. Third and final, tenant of self-compassion is defined by Dr. Kristin Knapp. Kindness over judgment. Imagine you’re sitting next to yourself on a park bench and you’re laying all of these hard thoughts out there. Nobody’s gonna be into me. I can’t trust people that are into me because something’s going to go wrong.

What would kindness sound like? What would your best friend who always knows what to say, what would they say to you? It makes sense you feel this way. Of course you’re struggling. This is really vulnerable. Whereas most of y’all and myself at times, many times in my life, because I’m human, go into self blame mode, shut down mode when it comes to having hard thoughts that feel like the truth because you practice them a billion times like people aren’t gonna be into me.

And you might say, Lily, nobody’s been into me or the people that have been into me, I’ve not been into. So like, these are not just thoughts, this is lived experience. And I would say, yes, yes, you have lived experience. Both and, if your lived experience right now was all that you would ever experience, you would be dead.

Lily @ Date Brazen (09:13.334)

Period. You are not dead. You are alive. I hope you’re gonna be alive for a really long time. I hope we’re gonna stick around and see how your story unfolds. Because you’re still alive, there is change that is possible. There are new opportunities that are possible, and you need to get yourself in the way of those aligned opportunities. And the way that you do that is by acknowledging the hard thought that is keeping you in a hidey hole of…

comfort zone and stuckness, have compassion for it, like we just talked about. Then final ACK, K-kind reframe. Kind reframe. It might be possible that I haven’t experienced everything yet. It might be possible that this thought is not a fact. It might be possible that I haven’t met everyone yet. It might be possible that I am enough.

starting with it might be possible so your brain can latch onto it and build a new neural pathway from there because what’s happening for a lot of folks who are trying to manifest love is that you are reaching for the goal thought. It’s possible. I am enough. Those are beautiful affirmations. I want you to practice them. But if you don’t believe them right now, then that work isn’t enough to building a new neural pathway. You have to start from a more accessible place.

It’s trying to believe like something that feels really inaccessible. Like I am enough. I am beautiful enough. I am sparkly enough. I am interesting enough. I am amazing enough. I am worthy as I am. Those are things are all true. I believe and know, but if they don’t feel true to you right now, then it’s like asking you to run a marathon tomorrow without any training. You’ve got to train.

your brain is really smart in a lot of ways, but really primitive in another lot of ways. Okay? It just wants to be safe and learning something new doesn’t necessarily feel safe all the time, which is why we use this self-compassion tool to create more emotional safety as you practice something new. I hope this is making sense. So more accessible thoughts start with it might be true that it might be possible that it might not be impossible that

Lily @ Date Brazen (11:37.267)

And then from there, you practice them out loud and often. You catch yourself in the default thought. Nobody that I’m into is into me. Hey, hey default thought, acknowledge it. Hey, I’m having this thought. Acknowledge it, take a deep breath. Compassion, ACK, compassion. It’s normal to have that thought. That’s a hard human thought. I’m here with you. Okay, kind reframe. It might be possible that I don’t know everything yet. It might be possible that more is out there.

One of my favorite baby step reframes for the kind of reframe step is it might be possible that I want something that’s not here yet, so let’s fucking go. It might be possible that I want something that’s not here yet, so let’s fucking go. This is not an end of the story moment. This is actually this podcast episode is an invitation to the next chapter. And that might sound a little corny, but I don’t care.

Change is possible for you. I’ve seen way too many people who feel like late bloomers in their dating lives, myself and my clients, to build this new self-concept where they believe in their worthiness, they believe in their enoughness, they start dating from that place, they start attracting better dates and opportunities than they thought possible, then they get into the best relationships of their lives or they trust themselves so hard that they attract new opportunities in work or in friendship. Like this is up-leveling your altitude.

but you need to practice thoughts to build to that new altitude that feel accessible now. For example, at a client who on a coaching session was working on this thought that she was undesirable and it really felt like mud in her spokes. It was like really hard and deeply ingrained from a lot of past experience, a lot of practice that I’m not desirable, I’m undesirable to keep herself safe. And so we acknowledged it, we used ACK. We acknowledged it. Then I said, what might self-compassion say?

And her response was, I am desirable. And I said, cool, cool, cool, let’s pause. That’s true. Like you are, you can be to yourself, you can be to the right people. Like that’s true, but you don’t believe it yet. So it’s not gonna actually help. She was like, wow. She was thinking that self-compassion was this sort of like projection onto her desired state of being desired self-belief.

Lily @ Date Brazen (13:57.417)

But really, self-compassion is just meeting yourself where you’re at right now and saying, that’s a really hard thought. I’m really human for having that thought. Then kind of reframe, it might be possible that I’m learning how to feel desirable for myself and then to other people who are right for me. So that’s step number one, ACK. If you’re struggling with feeling attractive, if you’re struggling with believing that somebody is gonna be into you, if you’re struggling with this thought like,

I don’t trust somebody who wants to be on my team like I was struggling with, then that step is going to change your life alone. I also want to say that distrust of new experiences or lack of belief that new experiences will happen is just very human. And so I’m here to tell you that if you are listening to this episode and you’re like, it’s impossible for me to believe that I’m worthy enough or that I’m desirable enough because I haven’t experienced that level of validation before romantically, especially in my life, it’s normal.

not to believe that something new will happen in your life. Why? Because your brain wants to be safe and right over learning something new. And it’s deeply vulnerable to put yourself out there to gather new evidence that you might be desirable enough, that you might be amazing enough, that you might be worthy as you are. That takes vulnerability to gather that new evidence. And to build that new belief, that takes a lot of vulnerability.

So that’s why in a couple of weeks we’re doing an episode on rejection resilience, because I think that a lot of folks are struggling with the potential for rejection in order to build new experiences in your love life and life in general. So that’s what we’re going to work on in a few weeks. So don’t worry, I’ve got you, but just know that it’s just really normal to distrust potentially new experiences. And I hope that that normalization gives you some permission to start playing around because our brain, it’s

It’s plastic. It’s neuroplastic. never, it’s not plastic, obviously, but we have neuroplasticity is what I’m trying to say. And the brain can change. Your circumstances can change. Your opportunities that you attract can change. Your level of confidence can change. And you can become the version of yourself who believes, hell yeah, I’m worthy of what I want. Hell yeah. People that are into me, of course they are. Hell yeah. I am undeniable.

Lily @ Date Brazen (16:18.207)

We’re building toward that in this podcast together, especially if you feel like a late bloomer, it is possible. And just know it’s normal if you don’t trust that it’s gonna come. I’m over here in Brooklyn believing it for you until you can believe it for yourself. The other thing that I want you to do to build this new belief is to practice curiosity over certainty. So you might feel certain that you’re not enough or that it’s not gonna happen or that it’s all over. And I want you to really train your brain to be more curious than that.

It’s sort of why I created the Thank You More Please Challenge because people were coming to me saying, it doesn’t exist, it’s not possible, there are no cuties in my area. And I said, okay, cool, I hear you acknowledging those human thoughts. Go do a Thank You More Please Challenge outside of your house. Go gather 10 slivers of evidence that what you want exists. When you see those things, when you experience those little micro moments of connection or flirting, say thank you more please out loud to recognize the small wins.

that do mean something. The brain loves small wins. Neuroplasticity loves small wins. So along the way, I really want you to reframe from certainty it’s never gonna happen, it’s not possible, anybody that’s into me, I’m not into, okay.

More curiosity, please. Might it be possible for you to go do a thank you more please challenge this week to gather 10 moments where you received compliments, where you received a little bit of attention or validation that you didn’t expect. Thank you more please. Some other action steps that you can do to start building the belief, start building the baby steps toward what I want is inevitable, I’m amazing, like I’m the shit. Building toward that, here’s some things that you can do.

because you deserve to feel that way about yourself. This is your one wild and precious life in the words of Mary Oliver. So why not think the best of yourself? Okay, some concrete action steps. Go do a thank you more please challenge where you notice 10 things going well, where you’re receiving support, validation, affection that you didn’t expect in a fun way. Like go say thank you more please to those 10 things. Go set a goal for yourself to give five compliments.

Lily @ Date Brazen (18:33.097)

go give five compliments. I’ve given this challenge to a couple of my clients and it’s going so, well because inevitably when you give more of what you want to receive, you receive more of what you want. So give five compliments and then whenever you receive a compliment, whether it’s in that conversation with that person that you’re complimenting or otherwise, your job is to say, thank you, thank you, thank you, I received that, thank you, I appreciate that. Instead of being like, no, no, no, no, no, thank you.

Finally, the 20 in 2 challenge, the bragging challenge that I teach inside of main character dating, where you can set a timer for two minutes and then try to write down 20 reasons that you are awesome while you love yourself. If you don’t get to 20, that’s okay. It’s a practice. So, and the two minutes can be kind of a fun time-bound way to get things on paper, to get out your head a little bit and onto paper. Like, why are you awesome? Why do you love yourself? And if you are struggling with coming up with some reasons,

and you have a close friend who you could talk to about this, send them this episode. Say, I’m working on believing that I’m the shit. I’m working on believing that people who I’m into will be into me. And I would love to know why you think I’m special. And I would love to share my thoughts on why you’re special in return, but I’m working on this thing about bragging and I just wanna know, what do you, like, this is really vulnerable, eek, but like, what do you think is special about me?

And then you could like build your list from there from your friend’s thoughts about you. And suddenly you just have more, you have more gristle for the mill. It’s a gross saying, but you have more information to start building off of, to start owning your awesomeness, to start stepping into your power and your love life and beyond. So the two tools that we talked about really were ACK in this episode, acknowledge, compassion, kind reframe about any thoughts that you want to start.

emerging out of any beliefs you want to start emerging out of about your desirability about possibility in your love life about Believing that the people you’re into will be into you in the future using a CK to build a new neural pathway and then Neuroplasticity loves small wins So how can you build some small wins to put in your belt to start? Creating more evidence in your brain that you are enough that you’re awesome that you are desirable

Lily @ Date Brazen (20:55.433)

the right people. get to be desirable to yourself, for yourself. Using that 20 and 2 challenge, the bragging challenge to get there as well. You’ve got this and I’ve got your back. If you liked this episode, then you’re going to freaking love my book, Thank You More Please, A Feminist’s Guide to Breaking Dumb Dating Rules and Finding Love. I have a whole ass chapter about bragging to build your belief in your worthiness. I have a whole ass chapter on how to do that in person.

how to date in person. I have a whole chapter on a feminist takedown of dating apps. It’s such a fun read if I do say so myself. And it’s full of my personal stories from my love life that I know will help you feel less alone in this journey. And so if you want to get thank you more, please go anywhere books are sold or go grab the audio book and you can get a special bonus at datebrazen.com slash book, which is called the dating life fix. And it has 10 issues that you’re probably facing in your dating life.

and exactly which podcast episodes to listen to to fix those problems or clean them up and move forward within 10 to 30 minutes. So you’re definitely going to want that bonus. And all you have to do is buy the book anywhere and enter your receipt number and you’ll get that bonus in your inbox. Again, that’s datebreason.com slash book and the book is sold anywhere books are sold. And I am so grateful to be in your earbuds whenever I am. I’m so grateful that you’re listening to this show. It’s been five years over five years of

growing and recording the Date Brazen podcast. So I’m really grateful that you’re here and I’m really grateful for your support. Have a great week and I’ll talk to you soon.

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.