In episode 283, I’m getting personal about how people pleasing made me settle in dating, friendship, and work, how it led to panic attacks on my lunch break, and the three-step formula I used to quit, one small choice at a time.

→ I thought I was and wanted “too much,” and how that kept me in a relationship where none of my emotional needs were met

→ How people pleasing was showing up in every relationship in my life, from texting clients at 10 p.m. to making every single plan for my friend group

→ How you can go from feeling sick with people pleasing, like I was, to building an expansive, joyful life as the main character

→ The unconventional way to use guilt as your roadmap to give yourself more permission

→ The three-step formula I used to quit people pleasing and build main character energy, even when I was afraid

Main Character Era — my small group 6-month mastermind for people-pleasing burnt-out feminists to build rock-solid self-trust and finally get what they want in love, friendship, and work — applications close tonight at midnight.

💎 Apply for Main Character Era: https://datebrazen.com/era

Work with Lily:

💎 Get the book, Thank You, More Please: https://datebrazen.com/book

💎 Join the Main Character Dating waitlist: https://datebrazen.com/dating

💎 Download my free Essence-Based Preferences Creation Guide: https://datebrazen.com/workbook

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💎 Follow me on TikTok: https://www.tiktok.com/@datebrazen

💎 Follow me on YouTube: https://www.youtube.com/@DateBrazen

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Show notes:

Lily @ Date Brazen (00:37)
I want to talk to you about people pleasing

specifically for dating. So I want to talk a little bit about that and how it came up for me. And in this live, I’m going to give you a formula to stop people pleasing tonight in one small, simple way that is going to start freeing you and showing you how you can live freer in the rest of your life.

So I don’t know, like almost 10 years ago now, I had what was like a really shiny life on the outside. I you know, felt like a late bloomer. And I had never had an adult boyfriend I had had like a high school boyfriend during my like love weights period where I thought that I was gonna like marry him and be a preacher’s wife

And when after I had like unpacked that and deconstructed that evangelical identity, I still felt like a late bloomer. I like literally didn’t know what to do in my dating life. And so when I started swiping, I was like sort of throwing spaghetti against the wall. I was like, I mean, he seems nice enough. They seem nice enough. Whatever. Okay. So I was settling on the dating app before I even went on a date. I don’t know if you can relate, probably you can. But

So I saw this guy on the dating app, and I thought, he looks cute. Actually, the piece of the story that I don’t really tell, you know, there’s so much to my life that isn’t on the internet. But I actually didn’t know if I wanted to go on a date. So this is my first people-pleasing thing. I didn’t know if I wanted to go on the date. I didn’t know if I was attracted to him. I didn’t know if he had been like communicative enough over text. So instead of trust, he asked me out on Bumble, and instead of trust.

Trusting myself to either say yes or no, I put it to a vote to my coworkers who I was with at the at that time. And I said, look at this guy. Should I go on a date with him? Yes or no? Again, felt like a late bloomer, didn’t know what I was doing. And so I literally put my phone up to my coworkers. I was like, You tell me, is he cute enough? Is he, is he, is he nice enough? Like, what do you what do you think? And they were like, Yes, go on the date, please. Like, you have no experience. You should definitely go on the date.

So I went on the date. He was like 25 minutes late. And so I sat there and he came in with a backpack and he was very disheveled. And I then proceeded to get like really drunk with him. And we did share a connection. We did have some big laughs.

And then afterward we made out and I felt like it was really sexy and cute. And then we we we did some fun stuff, and then like s very suddenly I started falling in love with this person. Okay. So then he tells me he loves me too. We’re now like two weeks into dating, saying I love you. It was wild stuff. Okay. Then we’re in a committed relationship. my god, I met this guy, I wasn’t sure I was gonna go on a date. I I am now in a relationship.

And talked about monogamy and we talked about that we wanted the same things and we talked about he was like meeting my checklist. He was really smart and kind and interesting and progressive and all these things, right? Check, check, check. We end up starting this committed monogamous relationship, and then we go on a trip together. It was Paris. Wow. Wild, wild first few months of a relationship. We go to Paris, and this man, on the first night in Paris, is sitting across from me and says,

is so shaky and nervous. I’m like, what’s going on? He’s like, Lily, I and you have to imagine before I get to this part, you have to imagine that I feel that my life, my dating life, is finally together. I, after so many years of not having sex, of feeling like Lily Bloomer, of feeling like like nobody likes me. My friends are always the ones that are ones that are chosen and I’m never the one that is chosen. And I don’t feel very attractive and all this stuff. You have to imagine like I am riding high on feeling chosen.

Even if there are a few things that are out of alignment, even if there are a few like yellow flags, I’m still like it’s shiny from the outside. I’m chosen. Okay. Then this man says to me, on the banks of the Seine in Paris, Lily, I need to tell you something. I need to be in an open relationship, to be in any relationship. And no.

Shade to people who are poly intentionally love ya. No shade to people who are open and want to be. But in that moment, my body knew that that was not the right choice for me. But because I was socialized to people, please, coupled with my desire to appear normal and to be in a relationship to prove to me that I was worthy of one, I said.

Sure. Sure, I’ll be in an open relationship with you. And he was like, whoo, okay, great. Glad to hear it. and then we began this relationship where I was doubting my wants and needs constantly because I thought they were too much. I want monogamy, that’s too much. Can’t do that, Lily. And I’m in love with this person, my first adult boyfriend. I’ve got like I I don’t know I again, I’m sort of like, well, I don’t know what I want. I can’t trust myself. Maybe I do want too much. Maybe I am too much. Maybe I

Maybe all these th and by the way, that lined up very neatly with the ways in childhood that as a young girl, I was taught to people please in order to be safe and to belong. So I the pipe was primed for me to be in a terrible toxic relationship where none of my emotional needs were met because I was taught from a very young age to people please and to acquiesce to other people’s wants and needs in order to belong.

People pleasing was my sort of like the way that I got by. And it honestly was pervasive beyond just my dating life. I was a top professional matchmaker at this same time. at that time, I didn’t have much control over my work life. there wasn’t much institutional support. I was texting my clients at 10 p.m.

People pleasing, like, yeah, we’ll definitely get on that tomorrow, right? I don’t know if you can relate with responding to Slack messages at 10 p.m. or 11 p.m. after you should have closed your laptop long ago, but you have this nagging, pervasive sense of, I’ve got this urgency to help people fix, to help support, to help caretake to people please in order to feel safe in your body and to feel like you are okay.

I know that I was really struggling with that in my work life. I was like burning the candle at both ends, people pleasing my clients, like people pleasing instead of owning a boundary and standing firm in it and trusting myself. In my you know, in in in my friendship life, I again I had this story that I was too much and I didn’t ever have a friend group. And then I had a friend group. finally have a friend group. my God, I’m somebody host friend group. And I was in New York.

And like it was so magical, I thought. But on the inside, I was making every single plan for them. I was texting them first always. and they just like weren’t interested in the kind of friendship that I really wanted, but I thought that I was too much for wanting reciprocal communication, for wanting them to text me first sometimes. And so I just want to show you how I was living.

So deeply and people pleasing that I could not see the forest for the trees. It was not only in dating in this relationship where none of my emotional needs were met. It was also in work and in friendship because I believe that the way we do one thing is the way we do everything. And so I I I really like struggled with shedding people pleasing. It felt like a foreign language. What do you mean? I mean, I would hear like therapists, I had started therapy already.

I’d hear therapists say like set a boundary or like you know trust yourself. But I didn’t know what any of that meant in practice. I didn’t know how to do that. I didn’t know how to shed the immense visceral fawning fear that came up when I wanted to make a decision that went in the face of what somebody else wanted for me. Like this boyfriend that I like was sort in love with at the time. I didn’t know how to do that.

And so the turning point for me was when I was having panic attacks on my lunch break. I literally became sick with people pleasing, with giving pieces of myself away to others in order for me to feel okay. And I remember it was honestly when I started to build date build date brazen and that I started to understand that.

Quitting people pleasing was a skill set. That quitting people pleasing happened one choice at a time. And at the time I was doing this by myself and building Date Brazen at the same time. And now this skill set of quitting people pleasing, it’s called main character energy. And it is buildable. It is three things that I’m gonna share in a second, but it is buildable. And I learned through like practicing it.

one small choice at a time.

I learned how to build an expansive, joyful life where I am a main character. My life isn’t perfect, but it’s expansive because of this skill set that I build and built and honed over years of main character energy. And now in main character era, my mastermind that I’ve led for the last four years, through with dozens of people building main character energy, quitting people pleasing daily.

Building this skill set so that they could heal their burnout, heal their people pleasing, and step into their most epic lives imaginable in love, friendship, and work. Now I get to accelerate their progress into main character energy with them over six months of intensive accountability-filled, one-on-one coaching-filled, coaching over six months in this small group with me azure group and one-on-one coach. So here is the skill set that helped me emerge from that toxic relationship.

quit people pleasing and build my company and build a reciprocal friend group as well. Because again, the way we do one thing is the way we do everything. There are three things that you need to know. Three things. Number one, you need a no guilt permission slip. When you feel guilty, like okay, for example, in your dating life, you find somebody on a dating app who is nice enough, but and they ask you out, but you’re really not feeling any attraction. And you feel guilt

Over not wanting to go on a date with them.

Instead of feeling the guilt and like being like, ooh, guilt’s scary. No. I want you to follow the guilt and notice how it is telling you where you need to give yourself permission. So many of you, and I was living this way too. Like a hall monitor was going to come and save me and like give me permission. That I that’s why I felt like I needed validation from that group of my coworkers about like whether or not I went on that freaking date.

It’s why I felt like I needed permission from my matchmaking colleagues and bosses to start Date Brazen when I first came up with the idea, which I ended up having to like really release the people-pleasing fantasy that people would understand what I wanted to do. And I had to strike out on my own with main character energy. You need to follow where you feel guilty for doing something that you want to do and write yourself a permission slip on paper. Literally becoming the decider.

Instead of waiting for the hall monitor to come and give you a pass. I need you to write yourself a permission slip. Even if you still feel guilty, we are following the guilt and choosing to write a permission slip. For example, I felt guilty for wanting to leave my matchmaking job. I felt guilty for wanting to leave the clients at the time that I was supporting in that matchmaking job, which I knew wasn’t the right fit for me long term. I had been there for years.

and I was really good at it, but I knew I needed to build date brazen. I knew in my body. And I needed to follow the guilt. Those clients would be taken care of by this institution that I worked for, right? But I needed to follow the guilt to get myself permission, right? I felt guilt for as wild as it sounds, that boyfriend that I had who literally

He wanted to be open, so I was open. He didn’t want to talk on the weekends, so I didn’t talk on the weekends. He didn’t want to truly, when I talk about this relationship, people are like, What? You were in this relationship? I’m like, yeah, it is wild what people pleasing will do to if you let it take over your life, it will. And it was in mind taking over. I was like living way out of alignment with what I wanted. I felt guilty for asserting my needs, but what did I need to do at that time? And what did I do to break up with him?

Followed the guilt and gave myself the permission that I needed. Okay. That’s the first step. Permission. Permission. Number two, self-trust. A lot of y’all and I thought that self-trust could only come after I’d had proof that I could trust myself. Okay. I thought my picker is terrible. I’ve been in this terrible relationship. I can’t fucking trust myself. What was I thinking? I can’t trust myself. With my friendships, I can’t trust myself to pick friends.

Or to text them or to to wait for them to text me first. I can’t trust myself. I I’ve always picked wrong in work. I can’t trust myself to build a business. I’ve never done it before. What are you even talking about? But the fallacy that I was under at that time that you might be too, is that self-trust is contingent on a perfect track record.

So many of us are using our past indecision, mistakes, fear, avoidance, using our past as evidence against the future we want to build for ourselves. And instead, self-trust is this generative thing that you can build choice by choice for yourself that is values-driven. So, what I mean by that.

Is this how you build self-trust? You need to, and this is what we do in main character era. This is what we’ll do on our kickoff call. I’ll help you identify your two core values. For me, my two core values are courage and belonging. Okay? So whenever I am with a decision, or whenever I feel I I feel the guilt, I notice it, I write myself a permission. So, Lily, you have permission in that case to break up with this guy. Lily, you have permission to break up with this.

Job and start your own business. So you have permission to go after a new kind of friend group, right? Permission, okay, done. But then comes the self trust part. One decision at a time, evaluate. Instead of casting a group poll out to your friends, be like, what should I do? And getting like five or six responses back that all say different things. Instead of researching another loop.

Instead of going to another therapy session where you’ve talked about this for the last two years, this decision you want to make, this thing you want to change, in st instead of doing that, right? Out instead of outsourcing just for a second. I love therapy, but like just for a second. What are your two core values? And what decision would be most aligned with those values? Tiny if you’re overwhelmed, you need to break it down further into a smaller decision. And then

You need to make the move with the 10 second dare. I’m taking a talk about that in a second. And then what does self-trust do? It may, it’s not contingent on a perfect decision. It’s not contingent on everything working out exactly how you’d hope the first time. It is contingent on did I make that decision in alignment with my values? If so, I get to be proud of that, I get to learn from that, and I get to make the next best self-trusting decision, even if I want to change.

My mind a little bit, Self-trust is not contingent on perfection, and that’s where a lot of people get stuck in building it. It is built small moment by small moment. It is built one choice at a time aligned with your values. Then the final step in this three-step process to build main character energy to quit people pleasing is the 10 second dare. This is massive, messy action.

And if you feel stuck in dating, if you felt like a light bloomer and you felt like I can’t date, I can’t date, I can’t date, I’m so afraid of dating, I’m so afraid of flirting in person. I’m so afraid of like I’m so afraid of trying. I’m so afraid of of looking foolish. I’m so afraid of this is where, with permission and self-trust, which is just essentially like safety in your body, a little bit more safety in your body to try new things and to be safe on the other side of it because you’re what? Being guided by your values.

Massive messy action, the 10 second dare is taking 10 seconds to do a thing. And this is where a lot of people get stuck in perfectionism too. I don’t know what to say. Well, what if you just said something and trusted you couldn’t say the wrong thing to the right person? I don’t know how to act on a date. Well, what if you decided that it was okay for you to you had permission to be awkward? You trusted that you would be okay on that date and that you would take care of yourself no matter what. you don’t have contingent self worth.

Because you have main character energy. And then you did 10 seconds of courage to ask a question, to go, to step in the date, to ask someone out, right? In a work scenario, that could look like permission to log off when you log off, trusting yourself that when the anxiety spikes, I have a plan. I’m gonna breathe through it. I’m choosing my value of, for my example, courage to guide this decision.

And no matter what, tomorrow I’m gonna be okay. I’m gonna break this cycle of overgiving at work. Then massive, messy action, the 10 second dare, the third and final step is 10 seconds of courage to keep closing the laptop, 10 seconds of courage to keep stopping that pattern of people pleasing and overgiving in order to belong. In your date, this applies to dating, friendship and work, it applies everywhere, but especially for clients who feel like late bloomers, who haven’t dated very much, or who have felt like they’re re-entering dating after a long time away.

This skill set of main character energy is going to change everything for you. Permission, self-trust, massive, messy action. It changes everything. It is the key in the formula to stopping your people-pleasing pattern. It is the key to taking your life back from that soul-sucking force called people-pleasing. And in main character era, this six-month mastermind that just opened for the first and only time this year.

Applications are open right now. go to the link in the description, to find out more. But basically, in main character era, we are going to help you quit people pleasing, build rock solid self-trust, and get what you want finally in love, friendship, and work. Because in the program, we help you build a hundred audacious self-serving dares. We help you, I help you step by step with your core values, with an audacious vision map.

We’re gonna come up with a vision for your love, friendship, and work life that feels audacious and self-serving and joyful. And I’m gonna help you break those big visions down into manageable dares that you’re gonna use this formula on permission, self-trust, massive, messy action, so that you can heal your burnout, so that you can start a consultancy business that you’ve always wanted to start so you can start dating joyfully and flirtily for the first time in your life.

So that you can finally ask your boss for that thing that you’ve been waiting to ask them. One of my clients, Katie, she came into the mastermind and she was like, I feel drawn to this. I don’t know exactly why. My friends would think that, like, what are you doing thinking about this? Because to them I looked like such a main character. But she knew she was living in her comfort zone and she knew that she was people pleasing every single day. She just couldn’t break out of that pattern. And so with Katie, when she came in the mastermind,

She was in a coven cheerleaders immediately of people that had her back who were going through this with her. And she had me as her coach holding her accountable every single week to her dares and her desires and to quit people pleasing. And all of that support led her to asking for a sabbatical at her company. Nobody had ever asked before for one. And she received it, a three-month sabbatical.

Because she came up with the pitch and she used 10 seconds of courage to do the pitch. She also realized that she wanted new friends. And so through the mastermind, she built a brand new core group of friends through joy-building activities that we helped her cultivate and build together. And we helped her build up, build the follow-through muscle, build the decide and done muscle, build the boundary muscle so that she could feel more empowered.

In her day-to-day life and in building new friendships. She built a whole new whole new core group of friends after the ma during the mastermind. And afterwards, she was like, My calendar is full of events with people that I didn’t know before this. This is wild. For my client Jackie, she came in so burnt out. And what is burnout? It’s fundamentally a disengagement from your needs. It is people pleasing, leading you into the ground. Okay. Burnout was hitting Jackie hard. And through this program,

And through the weekly group coaching, the daily written coaching, the dares one-on-one review that she got every single month with me from me. Jackie used main character energy to heal people pleasing by re-engaging with her needs. Jackie was able to identify what she really, really deeply wanted outside of people-pleasing her family, outside of people-pleasing at a job where she had to overgive in order for everything to run. She was the leader that everybody looked to.

She used the Hundred Dares Project to plug those people-pleasing leaks to heal her burnout. She realized she wanted to move across the world. She always knew in the back of her head that it was so dream, but she had been waiting, waiting for the perfect moment, waiting for her family to understand, waiting for the job to be exactly right. She also had been waiting to start her own consultancy business, which had been on the back burner forever. She started through main character era.

A an environmental consultancy business giving thousands of grant funding in just six months, literally, because she plugged the league of people pleasing and stepped into her main character energy. That and her story is wild, and these results are pretty typical in the program. She ended up attracting the sexiest dates of her life when she moved abroad because she was in her main character energy in the place that she felt self-trust had guided her to. My client.

my client A, who came on the podcast, she was a scientist and a poet. And she came into the mastermind feeling like, Am I even allowed to want to get this level of support? Is this too self-aggrandizing? Is this too self-indulgent? And she felt in her bones that this was the right next step for her, both for accountability, because otherwise she would not follow through on her big audacious dreams.

She was so deep in people pleasing that she couldn’t see straight. And because of the community, and because of the high level of coaching that we give every that I give every single week in this room, it’s a small group and we go fast together and we start your dares on day one. So client A had poetry in a drawer that she had been writing and hiding from people. She also, in her work life, was a scientist, she worked in a lab.

And she would never reach out to like scientific collaborators who she admired. She would never, she’d be like, Who am I to do that? You might notice that pattern for yourself. in dating, she was dating good on paper matches that did not feel exciting on the inside of them, on the inside of those dates. And so she was settling in all these ways, in her poetry, in her work life, in her dating life. By the end of main character era, A had a

Completely new energy because of her main character energy that we that I coached her in embodying, right? She took that poetry out of a drawer, applied to speak at a poetry conference, and got accepted to speak at a poetry, share her poetry at a conference. Hell yes. She started reaching out to scientific collaborators and decided she wanted to apply for a grant that she wouldn’t have otherwise because before she was stuck in this like people pleasing playing small mode, right?

With main character energy, she knew exactly how to start and follow through on this dare. And she won that grant. It was more than she invested in the mastermind. In her dating life, she was like before feeling like, I I I don’t know if I like this person. I don’t know if they’re right for me, but I need to go on a date because they’re good on paper. Afterward, she fully felt confident. She rebuilt, she did this without me knowing. And she brought it to the group coaching program, the group coaching call that week, and I was like floored in the best way.

She literally rebuilt her dating profile in the most joyful, fun way to literally be a bachelorette profile. She did a like a photo shoot with roses. She was like scripting her profile like it was like a bat because she loved the bachelorette. And so she scripted like she’s the bachelorette and this is her show. And like I was just thrilled. And she was having so much more fun with dating and going on much sexier dates, by the way.

Because of main character energy. And before she felt like a shrunken version of herself who was never going on dates that felt exciting because of people pleasing. And main character energy was the solve for all of that. These are just some of the examples of the results that my clients get in main character era. Clients are generally one of four types. They’re either the caretaker, taking care of everyone else before themselves.

They’re an overthinker. They’re researching all the all the time, never following through because of the the fear of being of of of doing the wrong thing, stuck in perfectionism. They’re the therapy grad, they know all the things, they’ve done all the therapy, done listen to the podcast, but they still feel stuck and aren’t taking action and don’t know why, because of the paralyzing people pleasing. Or they’re the blocked builder, where you know you have something on your heart you want to build, a dating life, a business.

a a promotion, a creative project, but you feel really blocked in building it and you don’t know why. These four types, this program was built for you, and will help you in your love life to step into your main character energy fully, to start flirting unapologetically, to start shooting your shot unapologetically, to start attracting the best dates of your life and the juiciest love life that you can imagine. It’ll help you in your work life to step into your power and agency as you step into your leadership with main character energy, whatever role you play.

And it’ll help you in your friendship life to build and foster reciprocal friendships that feel amazing on the inside because you will be showing up differently for yourself with your main character energy. And we are open for enrollment right now. Applications are open until next week. So we close for the first like we’re opening for the first time. We’re gonna close for the final time this year. We only open once a year, this mastermind, and it’ll be a small, powerful group with me as your coach.

And a small coven cheerleaders going alongside you. You get weekly, three times a month group coaching with me. We go three weeks on, one week rest for maximum integration. You get daily coaching, written coaching with me. in circle, you get a friendship building hub, you get one-on-one support monthly in Dares review. So I am reviewing and helping you come up with your Dares every single month to hit the Hundred Dares project effectively.

I’m gonna help you break down your big audacious goals into manageable small dares along the way so that you can hit your goals in the program in love, friendship, and work. and what else? we kick off with a virtual kickoff retreat, a Saturday retreat with just you, me, and this small covenant of cheerleaders on September twenty-sixth. So only like a week and a half away, we begin. And I would love to help you kick off this fall prioritizing yourself.

Making yourself a priority, finally quitting people pleasing for good, and stepping into your main character era, which will look like attracting the most expansive opportunities, finally having your back with self-trust, finally having more joy and pleasure and play in your life because of how you step into your main character energy. And again, attracting incredible things as a result. So all you gotta do to apply, it’s a 10-minute application. The questions alone will increase your main character energy.

So if you even have an inkling of curiosity about this program, go look at the application and start filling it out and submit it. You can, after submitting that application, you’ll be sent an email if you’re the right fit. And if you are, then you can either schedule an hour-long sales call with me that we’ll schedule sometime this week or early next week. And I’m actively filling the program, which is why I want you to take advantage of this moment

Fill out that application. Help help like yourself understand where your main character energy is right now, where you’re struggling. use that application as a self-assessment tool, and then we’ll have a sales call to talk all about it and to see if this is the right fit for you. I it’s an honor to be here. I love opening main character era. I’ve done it for the last four years. The results are incredible, and now it’s your turn to prioritize yourself.

applications close on Tuesday and so like let’s go. Let’s fucking go. I’ll talk to you soon.