275. If I Was Your Dating Coach This Summer, Here’s What I’d Tell You to Do

Overcoming Dating Fear & Rejection

If you’ve never been in a relationship before, or never been in a good one, and you identify with feelings of anxiety, hopelessness, or overwhelm when it comes to dating, and you just feel like it’s impossible for you to find love and it’s all over. This episode is for you.

This is exactly what I would do if I was your dating coach in the next three weeks, so you could build a joyful dating life, attract the best dates of your life, and make the right relationship inevitable this summer.

Inside Episode 275:

  • Why “it happens when you least expect it” is actually desire suppression in disguise, and what to do instead
  • How to build your matchmaker protocol: claim your essence-based preferences so you stop settling before you even get to the starting line
  • The vetting questions I used as a professional matchmaker to qualify the right people and disqualify the wrong ones without mind drama
  • Why rejection feels like death (it’s biological, not dramatic) and how to build a bounce back plan so it stops running your dating life
  • The Bounce Back protocol: a step-by-step rejection resilience plan you can write in your notes app right now

Work with Lily:

Show transcript:

 Lily (00:37)
Hey, gorgeous friends, and welcome to another episode of the Feminist Dating Show. I am so glad that you are here. If you have never been in a relationship or you’ve never been in a good one, and you identify with the feelings of anxiety, hopelessness, or overwhelm when it comes to dating, and you just feel like it’s impossible for you to find love and then it’s all over, this episode is for you.

This is exactly what I would do if I was your dating coach in the next three weeks inside of my program Main Character Dating, so that you could build a joyful dating life, attract the best dates of your life, and make the right relationship inevitable this summer. Main Character Dating is open for enrollment right freaking now until tonight, June 16th, 2026, at midnight Eastern, when we close our doors. The next time we open will be fall. And I really want you to utilize this highest opportunity time of the year this summer for IRL dating, especially.

And that’s what we’re gonna do inside of main character dating. So here’s what I would do if I was your dating coach. First of all, I would tell you that you need to detox from desire suppression. What do I mean by that? I need you to recognize where you’re trying to convince yourself that you don’t want a relationship because you’re afraid that it doesn’t actually exist or that wanting it makes you repulsive to the right people because it happens when you least expect it. I have never heard such a terrible piece of dating advice in my life as it happens when you least expect it.

Let’s call that what it is. Desire suppression. You are afraid that what you want doesn’t exist. And so your brain has done that human brain thing and centered the people who are wrong for you in whether or not you believe your own desires. You might be judging your own desire to find the right relationship because you think it makes you less of a badass feminist. No, wanting things doesn’t make you less of something else, it makes you human.

You want something and it’s not here yet. So of course you want romantic partnership in this life if that’s what you want. It’s so fun, right? Like you get to want fun and joy and pleasure in this life. So you are not less than also because you don’t have it yet. That’s that crappy double bind that I think patriarchal conditioning puts all of us in, especially women and people socialized as women, is this idea.

That wanting a relationship is pathetic and not having one already is pathetic, right? This like really crappy double bind. So I need you to identify if you are suppressing your desires in any way for romantic love, notice where patriarchal conditioning might be putting you in that crappy double bind. And I want you to give yourself permission that desire is your birthright. That’s a quote by Dr. Juliana Hauser. And it’s time for you to stop suppressing your own desires out of fear.

Because what’s the alternative? I really want you to play this out. You stop wanting what you want, which is really impossible, by the way. And then you just spend years with this dull hum of like, what if I had just tried differently? What if I had just shown up differently? What if I had actually asked for what I wanted? Learning how to attract and thrive in the right partnership is a simple set of skills. It is proximity to opportunity plus courageous behavior in the face of that opportunity.

It is building a feminist dating strategy where you know what you want. You ask for it without apology and without shrinking yourself. And you even raise your standards so that the wrong people for you see themselves out and the right people for you become apparent. This is essentially about not silencing yourself anymore at any level. Not silencing your desire for what you want in this one wild and precious life, in the words of Mary Oliver. Not silencing your desires when you meet somebody because you’re afraid that it’s gonna scare them off. No, say what you want.

Right. If you haven’t realized your desires yet, if they haven’t come to fruition yet, then let’s go. More is possible than you currently realize. And if you haven’t seen that the kind of people that you’re going on dates with prove to you that what you want exists, then I just gotta tell you, the right people for you are invisible to you right now. You just haven’t met them yet. So together, I want to build a feminist dating strategy with you that makes you a magnet for the right people and helps you confidently take up space with your desires. So

That’s the first thing I would say to you as your dating coach. Stop suppressing your desires. Then I would have you build this first skill of a matchmaker protocol. This is where you claim how you want to feel in the right relationship, even if you haven’t been in one yet. I need you to understand with clarity what you want in the right relationship so that you can actually start attracting it instead of settling before you even get to the starting line. This means claiming your essence based preferences.

Not a rigid checklist, not an open-minded and just nice with a job, but a living documentation of how you want to feel in the right partnership and what qualities make you feel that way. This applies to both logistics like the age range stuff, ⁓ the height stuff. You need to know how you want to feel with each of those sets of preferences logistically.

So for age range, you might want to feel like they understand your place in life. You’re in a similar place in life. They understand your references. You really like it’s about understanding, essentially, perhaps for you. So once you know how you want to feel with the right with the age range that you want, you can be open to being surprised by the package somebody comes in. If they’re plus or minus three to five years, either way on your age scale, right? This is where I hear a lot of people freaking out about like, my God, they’re too young for me, or my God, they’re a little too old for me, whatever. They’re not who I imagined.

But do they make you feel the way you want to feel though? Then keep going. That’s your metric. You are subtle proof when you have the metric of essence-based preferences. Then you also need to know like the personality traits and values that you want and how you hope those make you feel. So inside main character dating, my co-coaches and I go through this process with our clients that has you identifying the personality traits and values that you want.

With how they make you feel. Because this is the recipe for being open to being surprised by the right person and being settled-proof in the process. Because after every single date, I want you to tune in with how you felt on the date to gauge whether or not that person had the traits that you’re looking for, whether or not that person is the right kind of person for you. Once you know that, then I would have you build a vetting system. So

When I was a top professional matchmaker, I vetted over a thousand people for my clients on the phone. I would get on the phone with them, I would ask them a series of questions, not just do you want a relationship check yes or no? But I would be kind of sneaky. I would, based on my clients’ essence-based preferences, which I had them create with me, then I would go to this phone call and ask specific targeted questions to see whether or not that person had the qualities that my client was looking for.

I know how to help you build the question system, the communication system that you need for both IRL and online dating so that you can be your own expert matchmaker, so you can qualify the right people with ease and disqualify the wrong ones without mind drama. Okay. So when I was a matchmaker, these are the questions that I would use to have someone show me who they were. Because in the words of Dr. Maya Angelou, when someone shows you who they are, believe them the first time.

So you’d ask questions like, what’s bringing you joy lately to see how they answered? Or what’s made you laugh hardest lately to see how they answered? Or what are you hoping to find in your dating life? That’s one I really need you to ask before a date or on the first date. This will not scare off the right person. It will qualify you for the right relationship. The right person is also looking for someone who answers these questions in the way they’re looking for too, right? And you are uniquely qualified for the right person for you.

The way that they answer the question, you’re not looking for a rigid answer, but you’re looking for a spirit of generosity in the way they answer the question, it says everything about them. And when they ask the question back, you can share more about you and what you’re about, further qualifying and disqualifying, because you can share more about yourself and what you’re looking for, who you are, what lights you up. And this will allow you to see who the right people are and who the wrong people are faster.

So you know what you want. You have a vetting system to find it with a matchmaker protocol. I would have you shooting your shot after creating these things, challenging yourself to get out of your comfort zone this summer, to leave your couch, leave your house and meet cuties IRL and online with this simple step-by-step matchmaker protocol. Okay. Cutties outside of your house exist. You just need to go and have a spirit of openness to find them.

Summer is the highest opportunity time to be dating, especially in person. And I don’t want you to waste it believing that your dating life is over or that there aren’t people out there who are for you. They exist, they’re invisible to you right now, and you can go outside your house in search of them. So the second thing that you definitely need is a bounce back plan. Okay. Finding love, is simply about two things: proximity to opportunity and courageous behavior in the face of that opportunity. So when you have those two things.

You’re gonna be putting yourself out there. You’re gonna be meeting amazing people. It’ll be an expansion of opportunity. So there will be the possibility of rejection. It’s gonna suck. It’s gonna suck. Rejection sucks. If you we fear it, like we fear death neurobiologically, that makes sense because we were lived in caves. And when we were rejected, we were put out and we died of exposure, right? But why might you be stuck right now? Because you’re so afraid that rejection will mean something about you and your love life.

That you avoid it and then you avoid opportunity as well. Living courageously means rejection will happen, and rejection gets to be neutral when you have a bounce back plan. You need a step-by-step bounce back plan, aka a rejection resilience plan that when something hard happens, you have a system to follow for yourself to not only continue to put yourself out there powerfully and confidently, but to meet the right people for you and be unbothered by the wrong people for you, to de-center.

The people who are wrong for you and whether or not you put yourself out there. This is essentially again about stopping self-silencing, stopping letting the people who are wrong for you determine the outcome of your future. in your notes app of your phone, write down your rejection resilience plan or bounce back plan. Number one, you need to plan for your brain to freak out.

The thoughts that your might your brain might have are really mean to yourself out of self-protection and survival. You might have the thought this will always happen to me. I’m a loser and no one wants me. here’s more evidence that I’m unlovable or undesirable. How embarrassing. I’m such a failure and everyone can see. Woof, right? But your brain is a survival organ, right? It’s just trying to be safe. Secondarily,

In this notes app, I need you to write down S self-compassion. We’re gonna write down S O F T. S stands for self-compassion. That sounds like a very loving. Of course, I’m struggling like this. Of course, my brain is serving up these hard thoughts. I’m not alone. Oof, my brain is such a human brain right now. And fierce self-compassion might say, and we’re gonna move through this together. Like mama bear energy, like, and we’re gonna figure this out. We figured out hard things in the past, and it might be possible that our lives.

Aren’t over that that rejection didn’t kill us. So let’s do this together. Then third, you’re gonna write, ⁓ own your needs. You’re gonna write down a poo-poo platter of what you might need in a hard moment after rejection. Call a friend, send up the bat signal over text, eat a good meal, go on a walk, jump up and down, yell into a pillow, cry, wallow for a bit. If you’re in main character dating, you can ask for coaching, right?

You can text your therapist. What needs might you have? Again, we’re planning ahead to be less bothered by the experience of rejection, which just comes part in parcel with a more courageous life. Then we F feel our feelings. This is the part that everybody loves so much, except they don’t, because it’s the hardest part. And we’re taught that feeling your feelings makes you like a wallowy, like self-indulgent person or that it’s gonna last forever. But no, notice where is the feeling? What is the feeling?

And say to yourself, I’m willing to feel anything to be with you. A quote by a coach, Simone Sowell, that I really love. 90 seconds is all it takes. The Nagoski sisters in the book Burnout found that if you take like 90 seconds to feel your feelings, it closes the stress cycle instead of prolonging the feeling. What actually prolongs the feeling is if you deny it, if you say, I shouldn’t feel this, I shouldn’t feel so bad. It it’s not a big deal, right? Rejection just happens. No, feel those hard feelings.

of shame, embarrassment, whatever the fuck it is, so that you can move through it instead of getting stuck in it. Then finally, T, thoughts, not facts. It might be true that this is a hard moment and it will pass. It might be true that my human brain is just making up a story to keep me safe and I don’t have to believe it. I’m learning how to move through rejection faster. This hard moment is just a part of it. It might be true that I just haven’t met my person yet. This person wasn’t my person.

Ouch, and I’m gonna move forward. It might be true that rejection is just a filter and not an indictment on me or my future, and it still sucks really hard. I’m here for you. Finally, it might be true that maybe just maybe this is a part of a courageous big life, and I am safe. This is where you write down a useful and true baby step reframe thought to practice to build a new belief about yourself.

That will propel you forward because why? Thoughts create feelings, create actions, create results. So if you practice these thoughts that are more useful and true instead of toxic positivity, it’s all gonna be okay. Shut up, shut up, fear and shame. Like you’re you’re wrong. Don’t don’t don’t believe me. No, no, no, no, no. Don’t don’t try to muscle your way out of this. Move through this human experience with yourself with this protocol that I’ve just outlined for you. And then practice that new baby step reframe out loud and often.

It doesn’t matter if you have perfect belief. It matters if you go after what you want with the matchmaker protocol and the bounce back plan. That’s what makes finding the right people inevitable for you. And that’s what we do every single day inside of my program, Main Character Dating, which is open for enrollment until tonight, June 16th at midnight Eastern, June 16th, 2026. Even if you’ve never been in a relationship before, inside this program, side by side by your coven cheerleaders, you are gonna build.

A joyful dating life that makes attracting and thriving in this right relationship inevitable. Guess what your coupled friends may or may not have? Rejection, resilience. They may or not may not have self-trust in their relationship. They may or may not know how they want to feel in the right relationship. Maybe they just stumbled into a relationship. This program, this work is preparing you again to not only attract, but to thrive in the right relationship.

when that person shows up and surprises you because they exist, they’re just invisible to you right now. And how you show up matters to how you attract them. When they show up, you will want these skills and tools to help you thrive in that relationship because you know it’s overwhelming meeting the right person for you. You know what’s overwhelming receiving what you want. So

I want you to be practiced at trusting yourself right now so that you can, again, make attracting and thriving in the right relationship inevitable. In the next three weeks in main character dating, you are going to be doing the dating reset that I have for you, where you’re gonna be building your essence-based preferences, your matchmaker protocol, the vetting questions. You’re gonna be building your bounce back plan. You’re going to be building your online dating profile with essence-based preferences and the vetting questions.

We are going to be one-on-one reviewing your dating profile to make sure that it sings with everything that you need it to sing with to vet people before you even meet them. we’re also gonna help you come up with your communication plan so that you are unbothered by people who are wrong for you. You have a bless and release plan, you just let them go and you are going after the right people for you with even more quickness

we’re gonna build an IRL plan with you side by side. So, where do you need to go outside of your house? What do you need to do when you’re outside of your house? How can you learn how to flirt your way and build a flirting ladder to start practicing being your most courageous, flirty self, even if you’ve never flirted before, even if you’ve never been approached IRL before? This will have you becoming your own magnetic matchmaker for yourself and your love life. This is about becoming.

The most courageous magnetic version of you. And it’s based on the principle that your life isn’t over and that more is possible than you currently realize. So let’s fucking go. That’s what we’re gonna do in the next three weeks alone inside of main character dating, so that you can launch your most joyful dating life on day 22 And then for a year, you are going to be shooting your shot, going outside of your house, being courageous, flirting, going on the best dates of your life.

Submitting your dates for feedback so that we can one-on-one with our feedback system help you to heal your picker.

And it means 74% of the client’s dates are better than the last. They’re moving forward toward the right relationship. And the remaining percentage of people, ⁓ the 26% of people whose dates aren’t better than the last, they are being coached on how to bless and release swiftly. So they’re not wasting their time with the wrong people. So they’re settle-proof and they’re moving toward the right next date faster.

So check the link in the description of this episode for the link to join us in main character dating. We only open three times a year, and summer, as I’ve said, is the highest opportunity time for IRL dating specifically. And I really want to support you in taking advantage of that. Me and my small group coaching team can’t wait to be your dating coach officially. ⁓ the community is already so amazing, they can’t wait to meet you.

And if you just did these two things, the matchmaker protocol and the bounce back plan, your whole dating life would change. And that’s just the on-ramp in main character dating. So if you want to learn more, go to the link in the description of this episode. And I can’t wait to talk to you next week. Bye.