If you’ve ever hesitated to put yourself out there because what if they say no?, this episode of the Date Brazen Podcast is for you.
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We’re flipping the script on outdated dating rules that keep you passive and stuck. Instead of waiting, I’m teaching you how to co-create the dating life you want, how to shoot your shot like a boss, and actually enjoy the process (yes, really).

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Here’s what you’ll learn:
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Why I DON’T believe in the advice “If he wanted to he would”

Why “shooting your shot” is a dating superpower

The confidence shift that makes asking for what you want feel good​
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This episode is all about bold moves and big results. Listen now and start shaping your love life on your terms.

Links:

✨  Main Character Dating is open for enrollment. Join now. ✨

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 (00:00.238)

Hey gorgeous friends, welcome to another episode of the Date Phrase and Podcast. I’m so glad that you’re here because I’m about to share my hottest take that a lot of people will disagree with me on. And that’s okay, because I think that I’m right. And if you resonate, this episode is going to give you a guide to getting more of what you want this year. The thing that a lot of people in the dating world disagree with me on is that you need to shoot your shot 100 % of the time.

Literally, I want you to ask people out with abandon. I want you to tell people that you’re interested. I want you to go up to somebody out of the blue and say, hey, how’s it going? I want you to become that person who unabashedly, playfully, with unbothered energy, shoots their shot. And I think I know that this will get you more of what you want. So let’s get into this episode.

Hey, I’m Lily Womble, 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. Okay, let’s talk about…

why you might have been taught to not shoot your shot. You might have been taught, especially if you’re a woman or a person socialized as a woman listening to this, you probably were taught that it was a little too much to go up to somebody and shoot your shot, that it made you give away your power because if he wanted to, he would, and you need to let them come to you because keep a few of the cards to yourself and all of these things that I was taught.

like childhood about being a woman in my love life and my dating life were utter bullshit. Now, I do think that if you wanted to, you would. Let’s just unpack that for a second because I think that it’s a piece of advice that’s very cute to put in your little pocket and take around everywhere with you. But I don’t think that it’s necessarily great advice to date by. I do think the intention of it is so that you don’t do unnecessary emotional labor. I think that’s the intention, right?

Lily @ Date Brazen (02:30.542)

so that you don’t do all of the unnecessary emotional labor of shooting your shot and then planning the date and then micromanaging the date and then showing up early to the date and then checking afterward if the date went well. I do think that shooting your shot means that you have to expect co-creation, that being in the right relationship means that you need to expect co-creation. You are not going to be muscling yourself into the right relationship.

and the other person that you date is also not going to be muscling their way into the relationship. And I think that if he wanted to, he would for people who date men is in an effort to get you to stop doing all that unnecessary emotional labor, but really it puts you in the passenger seat. And personally, I don’t want to be in the passenger seat of a relationship. I want to be like two trees who are fully formed standing right next to each other. I want to be.

two cars driving to the same place together. I don’t want one partner to be the leader and one partner to be the follower. I’m talking about you expecting co-creation instead of expecting you to do all the work and them to do none or them to do all the work and you to do none. Like that’s not how human adult relationships work. And I think that that advice of if he wanted to, he would negate so much of the like nuance and context of people living busy lives. So

Shooting your shot is not about you doing all of the labor. It’s about playfully showing up. It’s about asking for what you want out loud and often. It’s about giving yourself the permission that you are the fucking main character of your love story and of your life enough so that you are willing to be awkward in the pursuit of getting what you want. Very similar.

to you getting a job. Now job search and dating, very different, right? Very different. Both and let’s use the job search as an example because it’s more neutral for a lot of people. In the job world, if you said, want my dream job and I’m not gonna ask for it because I’m nervous that if they think that I need them or want them that they’re gonna be turned off by that. And so I’m…

Lily @ Date Brazen (04:49.356)

just going to do my job, put my head down, and I think that the right job will come to me eventually. That’s not going lead to you getting your dream job, but it leads to you putting your head down and looking up 20 years later and being like, wait, I didn’t get what I because you didn’t ask for it because of the assumption that you were doing something wrong by asking for what you wanted because of the assumption that it was embarrassing to want what you want.

When did it become embarrassing to want what you want and ask for it out loud? yeah, because women and people socialized as women are taught to shrink their needs and desires so as not to disrupt the status quo. Okay? So now, alternatively with your dream job, you could say, I’m looking for my dream job and this is what it looks like, this is what it feels like, basically essence-based preferences for a job. And you know, I’m gonna start to ask for connections.

with my colleagues, I’m going to start to put it out there, what I want to do, even if it’s jumping tracks a little bit from my traditional career path and what I studied in school. I’m going to try and I’m going to put myself out there. I’m going to go to that conference, even though I’ve never been in this lane before and I haven’t been a manager before, I haven’t been an entrepreneur before or whatever it is. I’m going to put myself in these places where opportunity is rich and in those places of opportunity, I’m going to

really challenge myself to give my business card out to five new people and I’m going to follow up on those leads and I’m going to and what it will happen is that the right people for you in this context will sort of rise to the top. You’ll go to coffee with somebody and they’ll have an idea for you and you’ll take them up on it. It’s a co-creation in that way of you asking for what you want and knowing what you want with granularity draws it to you.

As opposed to taking a back seat with what you want and just saying, it’ll come because of fear of shooting your shot, because of fear of being awkward or looking desperate or whatever the fuck. You not asking for what you want leads to you not getting it. You, alternatively, asking for what you want means getting more of it. Now, like I tell my clients, when you shoot your shot, like I’m gonna teach you how to in this episode.

Lily @ Date Brazen (07:04.372)

It will lead to, it’s like riding bigger and bigger waves. If you were a surfer, you’re going to have access to so much more epic views. So many more epic views and moments where you’re on the wave top and you’re just becoming an expert surfer and that you’re on the wave top and you get to see the world from this new vantage point and more opportunities are there. And you’re like able to go to more places around the world to surf more opportunities, more opportunities. also means when you learn how to shoot your shot, when you learn how to become an expert surfer that you’re going to wipe out more.

Becoming an expert surfer, becoming someone who shoots their shot does not mean that rejection won’t come. In fact, it’ll come more often. Why? Because more opportunities will also come. When you get more opportunities, more rejection comes part and parcel because life is 50-50, 50 % hard, 50 % amazing.

And so the more you can normalize that rejection is going to come and it may not mean anything about me is a good baby step thought or rejection is going to come and I have the skills to care for myself through it with the self compassion that I’m learning on the date brazen podcast with the skills of mindset work of self permission that I’m learning with this podcast and my therapy, whatever you’re doing for your personal development, you can become unstoppable. You can release rejection as a deal breaker for you shooting your shot.

When you know how to have your own back, when you know how to care for your nervous system, I talked about in the last episode, episode 230, the idea of releasing fear in dating means doing self-compassion more often, means being in the practice of reducing cortisol and increasing resilience by being kind to yourself, by being mindful of those old default thoughts that pop up that say negative things like, see, you’re broken or see, you’re weird or see, it’s never gonna happen. Hey, default thought, hate thought, fact.

recognizing thoughts not facts is mindfulness. And also being in community, that’s self compassionate. Not being alone, normalizing your experience with other people who are doing this work with you is self compassion. you get to expect that when you shoot your shot, it’s going to lead to more opportunities. That when you shoot your shot, you are in the practice of getting what you want. You are in the practice of asking for what you want and therefore getting more of it. So.

Lily @ Date Brazen (09:22.04)

To start, I want you to really start embodying the identity of someone that gets what they want. Okay? Doesn’t mean that hard things don’t happen. Again, doesn’t mean that waves and crashes won’t happen and wipeouts won’t happen. It just means that you’re human and you’re trying something new. Get in the practice of acknowledging that you get what you want. Try this on. This week, do a thank you more please challenge. Whenever you get something that you want, for example, you’re hungry and you…

go outside your house to go get lunch and your favorite restaurant doesn’t have a line and you can just skip to the front. Thank you more please. I get what I want. Right? When you are really hungering for a friendship conversation and you text your best friend and they are available right away to chat. Thank you more please. I get what I want. This mindset of I get what I want will only help you to shoot your shot more IRL and online. It doesn’t mean that you won’t

not get what you want sometimes. It just means that you’re acknowledging that you also get what you want because probably confirmation bias mode in your brain, which is very normal, you just want to be safe and right, has been showing you all the evidence that you don’t get what you want. See, nobody approached me at that bar, I don’t get what I want. See, nobody asked me out on a dating app, I don’t get what I want. Let your brain be your human brain, practice self-compassion for all those times that you thought that you didn’t get what you wanted and you didn’t and you were rejected and it really hurt, both and.

As a both and, try on for size this week, where am I getting what I want? And how might I get more of what I want in my dating life by asking for more? Okay. So shooting your shot, asking someone out first, for example, or approaching a cutie at your gym or at a restaurant or at an event, it’s not giving away your power. It’s opening yourself up to opportunity. It’s opening yourself up to co-creation.

So how to shoot your shot IRL to open yourself up to more opportunity. It use my flirting 101 guide that I did in episode 229 called flirting 101 to learn how to flirt. It’s super simple. It’s just joyful courageous connection where you go up to somebody say hey, or you ask a genuine question. You start a conversation if they turn toward you their body language is turning toward you. They’re yes. Ending the conversation by keeping it going.

Lily @ Date Brazen (11:44.536)

Questions are being shared. eventually, five to 10 to 20 minutes in, ask, so random question, are you single? And then the conversation will go from there. Either they’ll say, no, I’m not single, and you’ll feel a little like, God, I can’t believe I did that. And then you’ll dip, fine, I’m willing to feel anything to be with myself. There’s nothing that I could say, do, or feel that would make me want to stop being my friend. Offering that to yourself really helps. Those are two thoughts by Simone Sol, a coach I admire.

You can, they could respond, are you single by saying, yeah, I’m single. And I’m not really interested in dating. Ew, awkward. That’s okay. Not a deal breaker. You can dip, no problem. They could also say, yeah, I’m single. And are you? And then you could say, yeah. Do you want to go to coffee? And then they could say, yeah, here’s my number. And then you can say, cool, I’ll text you. And then you could text and co-create a date. That’s co-creation. That’s shooting your shot. If you’re out and about,

Use the flirting 101 guide to approach somebody and ask a question and see if they’re interested to have a conversation. If you are at the gym, same, same approach somebody, say, Hey, how’s it going? Or, Hey, do you have any tips for this machine? I could use a little help if that’s genuinely you could use a little help. or you could just say, Hey, how’s it going? It’s not that deep. Come with a spirit of playful energy, right? Whenever you notice like desperate anxiety,

Like I gotta shoot my shot because Lily told me so and I’m not gonna get anything that I want because I’m not shooting my shot. Take a deep breath.

Say to yourself, like, this is normal. It’s okay that I’m nervous. And maybe I’m willing to try something new. Maybe it’s possible that something new could happen for me. Maybe I haven’t met my right person yet and shooting my shot is going to feel awkward and that’s okay. And then go forward with playful energy. People ask me, how do I shoot my shot at work? And for that, I would say you need to take that through a little bit of a decision matrix.

Lily @ Date Brazen (13:48.736)

Ask yourself questions like, are they my supervisor? Are there work policies involved of like, it’s not allowed to date at work? If you have a barrier to dating somebody at work that is super legitimate, then I would say, say thank you more please to the crush that you have in your own brain and keep it pushing in your dating life outside of work. If you’re self-employed and this person is somebody that’s a vendor or somebody that you work with, ask yourself before shooting your shot,

Could this lead to losing that business and am I willing to do that if I shoot my shot and it doesn’t go well? I think that it’s not that deep. I would just ask myself those questions to gauge whether not it was right for me to shoot my shot in a work scenario. More often than not, it might lead to complications that you don’t really need. And you can say thank you more please to that crush and keep it pushing. And or if the worst that could happen is that you might feel a little bit awkward.

Then shoot your shot. Being in the practice of shooting your shot means opening yourself up to more opportunities. It means co-creating with the right people. It means that you are more likely to get what you want. You are more likely in the job scenario that I mentioned a little while ago, you’re more likely to get your dream job if you’re opening yourself up to those opportunities and asking for connections and support more often.

You’re more likely to get what you want in that job scenario. Again, if you know what your dream job looks and feels like, if you know the essence of your dream job, the leadership treats their staff like this and they have this kind of benefits package and they have this kind of company culture, right? You know the essence of that job and that place. You’re much more likely to attract those aligned opportunities than not when you know the essence of what you want. Same, same with essence-based preferences in your love life. When you know the essence of that relationship,

How does it feel to be in their presence? What personality traits and values did they have that you find attractive? And how do you know that they have those personality traits and values? What questions are you asking to gauge that? Those qualifying, disqualifying questions. Knowing what you want with granularity means you’re more likely to find it, not in a rigid way, but in a way that encompasses the essence of that relationship that you’re looking for, how you want to feel. Shooting your shot similarly, asking for what you want out loud and often.

Lily @ Date Brazen (16:11.02)

means that you’re so much more likely to find it. So in terms of the like, if he wanted to, he would advice, I think that shoot your shot doesn’t mean doing all of the work. means showing up. Sending the first message on a dating app doesn’t mean you’re doing all the work. It just means you’re showing up and expressing interest and kicking something off. Asking someone out first looks like on a dating app or in person looks like saying, Hey, do you want to take this IRL or Hey, do you want to go to coffee sometime? Co-creation would sound like

Yeah, how about this date? Yeah, awesome. How about this neighborhood? Yeah, awesome. How about this place in this neighborhood? I have heard it has really good coffee. Amazing. See you there. And then they text you to confirm and then you show up and then they text afterward, right? That’s a co-created date versus do you want to go out? How’s this time? How’s this place? amazing. Okay, great. I’ll make the reservation and do everything for it. That’s muscling. That’s not what we want. We want a co-created date. And when you shoot your shot and do it with playfulness and expect co-creation, the right…

opportunities flow. Lastly, go shoot your shot. All it takes is 10 seconds of freaking courage. Go shoot your shot right now with a crush or with a work opportunity or with a friend that you want to make. Shoot your shot in the DMs. Shoot your shot wherever you can, wherever it feels aligned and exciting and playful. Go do it. What do you have to lose? This is your one wild and precious life. You’ve got this and I’ve got your back. Go shoot your shot. Bye.

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 datebrazen.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.