Dating can feel like a rollercoaster of emotions—excitement, hope, fear, and sometimes, pure panic. In this episode, we’re tackling the fear that keeps so many incredible people stuck on the sidelines. If you’ve ever thought, What if I get rejected? What if I say the wrong thing? What if I’m not enough?—this one’s for you.

I’ll walk you through how to move through dating fear with self-compassion, community, and a whole lot of self-trust. Because here’s the truth: fear is normal, and it doesn’t have to be in the driver’s seat.

You don’t have to be fearless to find love—you just have to be willing to take messy, brave action toward what you want.

Hit play, and let’s reframe your fear into power.

Takeaways:

✨ Self-compassion isn’t just nice; it literally helps your body handle stress better.

✨ Feeling afraid to date? That’s human. You’re not alone.

✨ Messy action beats overthinking every time.

✨ The right person won’t need you to perform or say the perfect thing.

✨ If you desire more, it’s because it’s possible for you.

Let’s go get you what you want.

Get your free Essence Based Preferences Guide ​here​.

Work with Lily:

Get Lily’s Book, Thank You More Please HERE.

Follow Lily on Instagram and Tiktok.

Subscribe to Lily’s Youtube channel HERE. 

Show transcript:

Lily @ Date Brazen (00:00.046)

Hey gorgeous friends, welcome to another episode of the Date Raising Podcast. So glad that you’re here. We’re gonna dive right in and my intention for this episode is to give you my hottest takes because I know that you have been delaying trying dating for a long time or you’ve gotten stuck after like a really disappointing date or attempt and you’re not like taking action for what you desire, which if you’re here probably is.

a joyful dating life, the right relationship, you’ve probably been stuck from taking action because of fear. And so in this episode, I’m going to outline exactly how to get over the fear of dating, whether you have been in no relationships or you just got out of a 20 year relationship. Let’s get into it.

Lily @ Date Brazen (00:48.879)

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 show you 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.

I’m gonna be really direct with you because I don’t think there’s time to waste. Not because you’re behind, not because you are less than because you’re single. I don’t believe that shit. I believe that you are whole and amazing right now and I don’t believe that your relationship status has any bearing on your value as a human being. Both and, you want something and it’s not here yet. That’s very normal, that’s very human, understandable. And because you want something and it’s not here yet,

My mindset is like, let’s fucking go. Your desire is your birthright. As one of my colleagues and friends, Dr. Julianna Hauser says, what you want matters. It’s not a matter of like, I wanna hurry up and date because there’s something wrong with me and I need to fix it and I need to prove that I’m not broken. No, no, no, no, no. You want something. So I want you to center your desire as evidence that what you want exists.

I’ve talked about this on the podcast before, but like the Wright brothers didn’t know that a plane could exist. They had a desire, a thought, they worked out it, they iterated, they failed. They faced a lot of rejection, I would imagine. Their desire was evidence that a plane could exist. Your desire for the Wright partnership gets to be evidence that it exists. And you don’t have to believe me right now, that’s okay, because it’s hard to believe that what you want exists, especially if you’ve never seen it or…

you’ve never been in a relationship before, or you just got out of a really bad relationship. I was in all three of those places. I felt like a late bloomer. didn’t have sex until my mid-20s, which compared to my peers, I felt light years behind. I felt so embarrassed by my lack of experience, both in dating and sex. I let that embarrassment really dictate my actions, and I would…

Lily @ Date Brazen (03:11.266)

accept attention and accept dates and accept relationships from people who were not right for me, who were not meeting my emotional needs, but who just wanted to be with me. And so I thought that proved that I wasn’t broken. I also, when I was in a really toxic relationship, I remember settling again and again and again. And this man in front of me met none of my emotional needs. It felt so comfortable because I thought that I was too much.

And I thought that to be in a relationship meant to feel lonely because that’s how I felt in all my relationships. I just say all of this to say that if you are afraid to start dating, I totally understand why you probably are afraid. You’re probably afraid of being in the wrong relationship. You’re probably afraid of rejection. You’re probably afraid of being judged. You’re probably afraid of those fears being true that you aren’t.

worthy of relationship, that you are broken, that you are weird and too much and also not enough at the same time. You’re afraid of those fears being true. I’m here to tell you on the other side of that fear, when I started learning these tools that I teach on this podcast, like self-compassion, like knowing my essence-based preferences, like willing to be awkward in the pursuit of what I wanted, when I chose to learn those new skills, my dating life,

became an act of self care and became actually fun and felt free. And I ended up having so much fun and meeting the love of my life as the bonus result. And I want the same for you. So on the other side of this fear, on the other side of not knowing how to date is just learning some new skills. That’s all you gotta do. And they may be uncomfortable, but I’m here to tell you that what you want is on the other side of you trying something new.

your life, because you’re watching this, because you’re listening to this, is not over. Hopefully our lives will be long. And so by you being here, it’s just evidence that your life isn’t over, that there’s more life and more experiences to have. And I am very serious about you getting what you want, you learning how to overcome this fear of dating.

Lily @ Date Brazen (05:29.327)

to get into the relationship that you want, to express your agency in your dating life because you’re alive and you’re vibrant and you’re on this planet right now. I’m very serious about you getting what you want. So let’s learn some fricking skills so that you can get over this fear of dating. Skill number one to get over the fear of dating is to practice self-compassion. Okay, you may roll your eyes. You may say, Lily, you’ve talked about this so much. I don’t get it. Here’s the deal.

In a 2014 study out of Stanford, it found that the practice of self-compassion, practice being a verb, not just a one-time thing, the practice of self-compassion reduced cortisol and increased resilience. The reason you’re stuck in fear is because your cortisol is high and your resilience is low. The way that you reverse that trend is by practicing self-compassion. As defined by Dr. Kristin Neff, there are three components of self-compassion. Number one, kindness over

Instead of judging yourself for having this fear, instead of talking to yourself like, shut up fear, you’re not right, Lily’s right, I love this one precious life and I’ve got to live it and shut up fear, I’m going to do it anyway. That is what I call the aggressive opposite voice, also known as some toxic positivity. Shut up fear, it’s okay, it’s going to be okay, I’m going to be great, it’s going be great. No.

Kindness over judgment. You’re judging yourself for having this fear. You’re human, you’re soft, you’re squishy. You’re afraid of being rejected because rejection feels like death because when we lived in caves, rejection literally meant death. So neurobiologically, it makes sense why you have this fear of dating because dating is vulnerable, okay? So kindness over judgment. Wow, it makes sense why I have this fear. This fear makes total sense. Instead of blaming yourself for not having experience yet, or instead of blaming yourself for

not having figured this out yet, why don’t you just be kind to yourself? I know it’s so much easier said than done, both and just try a little baby bit of it. Kindness sounds like giving yourself the benefit of your context. So if you are afraid of dating because you’ve never dated or you haven’t dated in a long time, giving yourself the benefit of your context could sound like, it makes sense why I’m afraid of dating because…

Lily @ Date Brazen (07:50.157)

I haven’t done it in 20 years or I haven’t done it ever. And that makes sense because I was caretaking for a relative and I really didn’t have the emotional capacity to date or it makes total sense why I fear dating because I went through such a horrific breakup and I never want that to happen again. It makes total sense why I have this fear coming up. It’s just trying to protect me. Kindness over judgment. Number two, as defined by Dr. Kristin Neff, the three pillars of self-compassion. Number two,

Community over isolation. Normalize that you’re not alone. I talk to so many amazing human beings every single day. Many of them decide to join us in main character dating because of this reason, among other reasons, that they are done feeling alone, that shame breeds in silence. And if you’re feeling shame about your lack of dating experience or about your experiences in the past, or you are afraid you scare people off because of your

or ambition or your amazing doctorate or you’re afraid you scare people off because of your big personality like I was, it’s okay. You’re not alone. If you’re afraid you scare people off because you’ve never been in a relationship before, you are not alone. And if you feel shame about any of that, it’s just gonna breed in silence. The more you can bring yourself into the light, into community, into belonging, the more you are willing.

to share with a close friend that you love and trust, hey, I’m really fearful in my dating life and here’s why. The more you can allow yourself to be held and belonging, the more subtle proof you are in this life. What happens when you are feeling lonely and isolated in your dating life, and I’ve seen this from my own personal experience, is that you are so much more likely to settle.

because loneliness and isolation feel like your status quo, you’re more likely to choose a relationship or a situationship that perpetuates your status quo. Why? Because the brain is more interested in being right than learning something new. It’s more interested in being in a comfort zone, even if that comfort zone is one where you feel lonely, than it is in learning something new and being in belonging, because you have the fear that people are gonna judge you when you step into the light, when you step into community.

Lily @ Date Brazen (10:08.978)

That just means you gotta find the right community for you. And that’s why I started this podcast, to normalize the shit out of your experience and give you a different path forward than the shamey, self-blamey, lonely status quo. Community over isolation is self-compassion. Third and final pillar of self-compassion is mindfulness over over-identification. Okay, so these are Dr. Kristin Neff’s words. I’m gonna break them down for you, make them really, really clear if they’re unclear.

Mindfulness just means being aware of your thoughts. Thoughts are sentences in your brain. Thoughts are not facts. They are emotional interpretations of the world around you. They are sentences that your brain makes up because of any given scenario or circumstance. For example, I look outside right now, it’s pretty gray in New York. I could, and it’s rainy and it’s a little snowy and sleety. I could look at that circumstance of

It’s gray outside my window and I could say, God, it’s so gloomy and this kind of day gives me no energy, I hate it. That could be a thought that I have. It’s a thought, not a fact, it’s a thought. It’s an emotional interpretation of that circumstance. An equally possible thought could be, ooh, cozy day in this gray, cold weather. Let me cozy up with a blanket and make my…

a little Harry Potter playlist and get cozy. How fun. That’s an equally possible thought. Thoughts are not facts. They are emotional interpretations of the world around you. And you get to be aware of your thoughts and with self-compassion, create new baby step thoughts that produce more feelings and actions that lead you toward what you want. For example, being aware of your thoughts sounds like

You having the fearful thought, I’m never going to find somebody, what I want is impossible. Okay, you’re having that thought. Fine, you’re human. I want you to be aware of that thought, mindful of that thought when you have it. Instead of trying to push it away, instead of trying to push it down so far that you don’t hear it anymore because it feels so true. What if you were just like, okay, that’s a thought, not a fact. It feels true right now because I practiced it a bazillion times, not because it actually is true. So.

Lily @ Date Brazen (12:34.984)

you acknowledge the default thought. Mindfulness over identification. Over identification is saying, holy shit, I’m having this thought. That means that it’s a fact. Better push it away because it’s really scary. And I don’t wanna think that about myself. Mindfulness, just say, hey, I’m having this thought. It’s not a fact. That’s really normal, self-compassion. And it might be true.

that that’s just a human thought. That’s the like baby step reframe. Instead of going to toxic positivity, instead of aggressively opposing that hard thought, just be like, you’re thought, not a fact. And it might be true that you’re just a thought. It might be true that more is possible than I currently realize. Self-compassion is the salve to that dating fear. It is holding yourself, turning toward yourself like you would a close friend. You’re lingering in that fear because you’re not only fearful, you’re blaming yourself for being fearful.

And that creates even more stuckness. So the more you can normalize your experience, the more you can acknowledge your thoughts as they appear in your brain as thoughts, not facts, the more kind you can be to yourself, the higher resilience you’re gonna have and the lower cortisol you’re gonna have, the lower stress you’re gonna have. This is the mindset work that is really crucial to getting over the fear of dating. And then,

When you have gone through that, when you feel a little more possibility, when you feel a little more opening to trying something new because suddenly you have more emotional safety in your body, you’re not trying something new because you don’t feel safe to do it yet. Self-compassion will create more safety in your nervous system and your body to try new things. That’s why when you’re on TikTok or Instagram or YouTube, whatever, I’m on all three platforms. Hello, at-date prison.

Okay, when you’re like looking at a coach’s stuff and you’re like, I wanna do this and I wanna start dating, here’s the checklist. And if you have fear in the way, if you feel constipated with all of that fear, you’re not gonna take the actions. No matter how good the actions may seem, no matter how powerful the actions may seem, you’re not gonna take them because of the fear. So to get over the fear, you gotta do the mindset work. You gotta sit down and do those three things.

Lily @ Date Brazen (14:44.052)

Kindness community and mindfulness like literally five minutes in your journal I’m going through each of those pillars writing yourself a little self-compassion Letter dr. Kristin Neff if you haven’t been able to tell I’m a big fan Come on the podcast dr. Kristin Neff on her website self compassion org She has free five minute ten minute 20 minute self compassion meditations. It’s why self compassion is a crucial

pillar of my work, not only in my book, thank you more please, but in my programs. I teach it in my own way of course, but this shit matters to you getting over your fear and trying something new. Now, once you do that work of creating the emotional safety in your body, you get to move on to the action steps, which we’re gonna talk about right after this message from our sponsor.

Let me know if this sounds familiar. You’ve been climbing the ladder at work. You’re basically a badass. You have amazing friendships. You go on beautiful trips. You indulge in self-care regularly. And you have a little bit of a secret. You want to find the right partnership and you’re afraid that it’s too late. You’re afraid that it came so easily for your friends and not for you because something’s wrong or because you’re broken somehow. You’re not.

And the way that you were taught to date is stuck in the patriarchal dark ages. The way that you were taught to own what you want and attract more was based in an old paradigm where you had to shrink your needs and desires. There’s a reason why dating has felt miserable up until now. It’s because you maybe haven’t been centering yourself enough and you maybe have been putting up with so much less than you deserve for fear that what you want isn’t possible.

there is a different way forward. All of this is why I wrote my book, Thank You More Please, A Feminist Guide to Breaking Dumb Dating Rules and Finding Love, which is going to be your step-by-step guide to detoxing from those toxic dating apps that have you stuck in a download delete cycle. You’re going to finally own everything that you want without apology with essence-based preferences, and you’re going to learn how to create an intentional, joyful dating strategy

Lily @ Date Brazen (17:01.938)

both online and IRL, one that magnetizes the right partner to you. In this book, I not only share my personal story of how I went from feeling like a late bloomer to meeting the love of my life with these exact tools, I share stories from my clients who did the same thing. And now I want you to pick up this book and start attracting the right partner with a joyful dating life. You can get this book, Thank You More Please, anywhere books are sold.

And you can get a special bonus at datebrazen.com slash book. You are right on time for this. I can’t wait for you to read Thank You More, Please. Now let’s get back to the episode. So how do you start dating if you’re just now getting over the fear of dating? I’m so glad you asked. I have a whole episode of the podcast, episode 136 called Where Do I Even Start?

that outlines like all the steps that I would recommend if you’re just starting dating, especially if you’re just getting over this fear of dating, to do it messily and effectively. So that includes the essence-based preferences. It includes choosing, qualifying, disqualifying questions, just a few to gauge whether or not somebody has your essence-based preferences, both online and in person. That looks like asking something intentional like what’s bringing you joy lately or what’s made you laugh the hardest lately or…

Who do you look up to? Who are you admiring and why? Or what are you proudest of that you’ve created in the last year? These deeper qualifying, disqualifying questions will allow you to see who’s right for you and wrong for you pretty quickly, both in-person and online. I also recommend having a dating app plan that is boundary as hell. I recommend one dating app, 20 minutes a day, no more. Put your phone down when you get activated.

Do this self-compassion work when you notice that you’re feeling upset after a dating app because they’re hard on your brain, body, and nervous system. You’re seeing faces and you might see a face that looks like your ex or you might be reminded of those old default thoughts that you’re working to move through with self-compassion. So be kind to yourself with a dating app. No notifications and open every conversation with a match with an intentional question like what’s bringing you joy lately?

Lily @ Date Brazen (19:19.442)

and do not do the extra emotional labor of making a bespoke message for every single match. That’s unnecessary. You can just open with, hey, Shelly, hey, Ben, love your profile. What’s brought you joy lately? And then once you create some like momentum with your online dating life, even if that’s just getting on for 10, 20 minutes a day, even if you don’t have so many matches, it doesn’t really matter because your metric of success needs to be how

you move forward messily, how you try new things, how you care for yourself when fear pops up. If you measure those things, which are within your control, you will be moving forward so much faster than if you measured success by the number of matches or messages that you had, or by the number of dates you had on your calendar. If you fully commit yourself to centering your desire, knowing your preferences, choosing to take messy, massive action,

choosing to care for yourself when you are activated with self-compassion, you are going to move forward so much faster. You are not going to burn out. You are not going to get stuck. And you are going to magnetize the right kind of people to you because of how much space you’re taking up with your desires. Again, your desire for more gets to be evidence that it exists. I also, as you know, if you’ve listened to the podcast, love in-person dating. There are whole chapters on in-person dating and dating app strategy with a feminist lens in my book, Thank You More, Please.

and in my program, Main Character Dating. Episode 164 of the Date Brazen podcast on Apple Podcasts or Spotify or wherever you could podcasts is all about doing in-person dating if you’re scared to start. So I really recommend you dive into that episode for all of those juicy strategies. So how do you get over the fear of dating? You practice self-compassion and you do it messily. You do it imperfectly. You let yourself off the hook for all of those perfectionistic standards that you have for yourself.

and you just take one messy step forward at a time. That is how you date and find love without like rigidity, without patriarchal dating rules telling you to be small and play small and be embarrassed for your lack of experience. No, no, no, no, no. You’re right on time. What you want exists. Your desire for more is evidence that exists. You can’t say the wrong thing to the right person. You are for the few, not for the many. You know what you want. You get to take up space with what you want.

Lily @ Date Brazen (21:44.87)

Owning what you want and asking for it means that you’re more likely to find it. And you can also build hope at any time with a thank you more please challenge, meaning go out of your house and look for tiny slivers of evidence that what you want exists for seven days and keep track of the evidence. And when you see a cutie and you make eye contact and you smile, say thank you more please. When you have a flirty conversation with your barista, say thank you more please as you’re exiting the coffee shop. Own what you want.

Be unafraid to care for yourself and your nervous system along the way. Acknowledge this is fucking vulnerable. It is hard. And you get to want what you want. So let’s fucking go. You’ve got this and I’ve got your back. Can’t wait to talk to you next week. Thanks for listening to the Date Brazen podcast. If you liked this episode, then you’re going to 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.