The way you do one thing is the way you do everything.

So when you’re stressed about the question “when is the right time to have sex??” and outsource your answer to another dating expert or another tiktoker, I hear an opportunity to build a life changing skillset that will create clarity for this question (and all questions)….

That skillset? Self-trust.

When you build the skill set of self-trust, with sex, with friendships, with romance, with work, it all gets more easeful.

Episode 281 unpacks what this question is really asking and gives you a framework to come to your best answer, whatever it is. Not just for this. For everything.

Because the skillset of self-trust will help you get clarity everywhere.

Inside this episode:

→ Self-trust defined: the firm reliance on the integrity of yourself. It does not mean everything goes your way. It means you will have your back no matter what happens.

→ ACK. Acknowledge, compassion, kind reframe. The self-coaching tool Lily teaches in main character dating, applied to a decision you have been agonizing over.

→ The small self-trusting decisions that you can make today that will start to build self-trust.

💎 Join my free live training, Quit Being the Best Friend: How to Stop People Pleasing and Finally Get What You Want in Love, Friendship, and Work Without Overthinking and Anxiety: https://datebrazen.com/best-friend

💎 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

💎 Follow me on Instagram: https://www.instagram.com/datebrazen/

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

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

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Show transcript:

lily (00:00)
Hey, gorgeous friends, welcome to another episode of the Feminist Dating Show. I’m so glad that you’re here. Today, I’m gonna give you the definitive answer of when is the right time to have sex when you’re starting to date somebody? Wouldn’t it be so nice if I had exactly the right answer for every single one of you? Well, so this is a question that I get all the time in main character dating: When do I have sex? Do I wait to have sex?

I a lot of stress is around this question, a lot of fear, a lot of anxiety, a lot of I’ve got to get it right or else. And so today I want to unpack what this question really is asking and what it means for your self-trust. And I’m gonna give you a framework to decide not only the answer to this question, but the answer to everything in your life with a more self-trusting framework so that you can actually trust yourself instead of outsourcing your

Trust your rules, your actions to another TikToker, another expert. Because honestly, you are the keeper of all of your best answers. And if you don’t believe me yet, I’m gonna show you how right after this.

episode is brought to you by my upcoming live free training that I’ve never ever offered before. And I’m so excited to see you there live. It is called Quit Being the Best Friend: How to Stop People Pleasing and Finally Get What You Want in Love, Friendship, and Work Without Overthinking and Anxiety. It is Live. I am teaching it on September 15th.

And inside, you are gonna learn how to build main character energy in your life today, even if you feel like a late bloomer, even if you overthink every decision, even if you have a dream in a drawer that you’ve been blocked from starting to build for years. I’m gonna teach you how to get up off your couch without overthinking and anxiety, start shooting your shots, start getting what you want without all of the people pleasing nonsense that you’ve been socialized to do in life.

And we’re gonna heal that shit and get you on your main character journey toward the love life, the friendship life, the work life that you desire. Maybe you’ve felt like you secretly desire, you haven’t said it out loud yet, or maybe you have known for a long time what you want and you’ve been stalled out and going for it. I’m gonna teach you how to get up off your couch with main character energy and start creating that shit in the real world.

Starting on September 15th. So you’re gonna want to be there live. Go to the link in the description of this episode. I cannot wait to coach your face off there. And on that live call, doors open to my mastermind main character era, which only opens once a year. And I can’t wait to share more soon. Okay, let’s get into the episode. Okay, I get this question a lot, as I said in the intro, when should I have sex? I shouldn’t have sex at this time because

The old-fashioned dating advice of like, who would want the cow if you gave the milk away for free? Such sexism. Okay, in that piece of advice. maybe you’ve listened to a dating expert who says you should always wait until the third date to have sex. Maybe your mom said, wait until marriage. Maybe you follow a TikToker who you really enjoy their content and they say, the only reason I found

Love and the found the person who was right for me after years of dating is because I waited three months to have sex and that proved to me that they really wanted me and that they were gonna stick around. Okay. Right. Underneath all of this, when should I have sex? this person said this time is the fearful voice thinking that there is a right answer that makes someone else stick around, that there is a wrong time to have sex and a right time, and that by following someone else’s rule, you’ll get it right.

But better pick the right person and the right rule to follow, or else so much pressure. So much pressure. And honestly, underneath it all is a lack of self-trust, a fear that you cannot trust your decisions. Because, you know, the thing that I hear and have experienced for myself is that, if you trust yourself and it doesn’t work out, then you were wrong and you aren’t trustworthy. I see this a lot.

For people who feel like late bloomers, in this idea of like, I can’t trust myself, I’ve never been in a relationship before. I can’t trust myself, I’ve never dated before. I can’t trust myself, fill in the blank. I haven’t gotten what I wanted, so I can’t have self-trust. Underneath that, we’re spelunking today, y’all. Underneath that is this idea that there’s a perfect, unique set of the there’s a perfect set of circumstances that would lead you to being trustworthy. And to be trustworthy, you have to have gotten

All that you want already to know that it’s okay to trust yourself because you got what you want. It’s this conditional relationship with yourself that’s got to stop because it’s stressful, but also because good things happen when you learn how to trust yourself. This is a lifelong skill we’re talking about that’s gonna have you not only you know, having more pleasurable connection with yourself, but with others.

You’re gonna when you build the skill set of self-trust, like I’m gonna talk about today, with sex, with friendships, with romance, with work, it all will get more easeful when you have the skill set of self-trust.

Okay, so for the sex thing in particular, I get that it’s vulnerable as hell. It is hard to know who will stick around and who will leave, who is in alignment or who just wants to have sex. Some people lie, right? Some people say, I want a relationship so badly, and then like they are really intentional. And then when you have sex, they ghost or whatever. Some people misrepresent themselves. I get that the idea of the rule.

Is that there’s a perfect amount of time that will solve for this variable. But I’m here to tell you that the wrong people are the wrong people are the wrong people, just like the right people are the right people The perfect and right answer for you of when to have sex and when to wait is self-trust. Because all of this shit is made up. All of it. And what will help you figure out the right time for yourself is this simple skill set that is buildable.

Of self-trust. I believe and know that the way you do one thing is the way you do everything. So I picked this question of like when’s the right time to have sex, both because I hear it all the time and I want to help you come to your best answer, whatever it is, and because I know that this is a microcosm of a deeper conversation about self-trust.

So maybe you clicked on this title because it had sex in the title. And maybe you’re listening to this episode and you’re like, whoa, we’re gonna be talking about something way deeper than just when do I have sex for the first time. Yeah. Welcome to the way you do one thing is the way you do everything. Okay. So let’s define the concept of self-trust together, shall we? Psychology today, this is a quote from psychology today. Self-trust is not trusting yourself to know all the answers, nor is it believing that you will always do the right things.

It’s having the conviction, the belief that you will be kind and respectful to yourself regardless of the outcome of your efforts. Acknowledging, and this is my editorializing, like acknowledging you’re not in control of how things go. It’s not like if you have perfect self-trust, everything will always go your way.

The definition of self-trust is the firm reliance on the integrity of yourself. This is dependent on your values to make decisions that are right for you in any given moment. So in main character era, my mastermind, we come up with your two core values in our kickoff retreat, happening on Saturday, September 26th. The doors open soon to this cohort, September 15th. Okay, but I digress. So we come up with your two core values in the kickoff retreat.

We also use the Audacity Map to identify the self-trust gaps in your love, friendship, and work life, i.e., where do things not feel in alignment, where are you feeling sticky, stuck, whatever. Then we build out 100 self-trusting dares based on your values and where you feel stuck. So we are essentially from the bottom up, top down, aligning your choices with your values and helping you do so.

With the act, the practice of self-trust. Let me use an example from my own life to sort of define this self-trust. I went on a date with Chris, my first date with Chris, and it went really, really well. It was so fun. It was connective. He I was freezing cold. It was cold and rainy outside in November tw 2017. And he held my hands to warm them up. And it felt just like so, I just remember feeling like,

Electric, this just warmth, not a and not it didn’t feel chaotic, it didn’t feel like overwhelming. I just felt very dropped into my body and this like warmth in his presence. I felt seen, safe, held, belonging, all the things in my essence-based preferences that I wanted to feel. We kissed at the end of that date. I had to go somewhere, he had to go somewhere, and we kissed, and it was so great. And I trusted myself to.

Like I felt like, yes, this feels right. I want to kiss him. And then later on that night, I actually went over to his house because he he at the time was room his roommate was a friend. Or he had roommates who were my friends. And I went over under the guise of like, let me just hang out with my friends, knowing that Chris was there. Okay. And Chris and I ended up doing really sexy things that night, right? And I came from this like evangelical love weights background.

where I didn’t have sex until I was 25. I felt really eternally behind. And I know that a lot of people share that. so by the time I met Chris, I didn’t really have much sexual experience, but I trusted myself because of the way he made me feel, felt in alignment with my essence-based preferences. I trusted myself and his, you know, w how he was presenting to me.

I trusted myself to do sexy things that night, even if I had been nervous. And I I also wasn’t really into casual sex. So I was making the choice that, like, no matter what happened with this person in the future, which I had an inkling that this was something deeper than just one night. I trusted myself to do sexy things. And eventually, I think in the first week had sex, and it he was my forever person. This is why I don’t, you know.

It is all rooted in self-trust. You can be with somebody who is not the right person and wait three months to have sex with them and they’re still not the right person. You can not wait and have sex on the first date with somebody that eventually is your life partner. You just really never know. All you have is self-trust with this is why I want you to tune in with how you feel. We’re gonna talk about how to tune in with your self-trust in a moment, but like tuning in with your values, tuning in with how you wanna feel, tuning in with whether or not they are generous in their communication and their

style of being. And then tuning in with your body of like, what do I want? Now, I want to introduce a little bit of like nuance here because I think the concept of what do I want can be clouded by scarcity, can be clouded by fear, can be clouded by self-doubt,

And I’m gonna teach you in a moment a strategy to move through that fear, to move through that scarcity, to come deeper into self-trust that is in alignment with your values and in alignment with what your body wants.

You can also have moments where your body wants to like bang it out, but you know the person across from you isn’t your forever person. And as long as it’s consenting and as long as you’re like putting on the table what you want, like you can say, I I’m ex I would love to hook up. I’m not really looking for anything serious, but I’d love to hook up. You can you can be honest, right? And be in alignment and integrity with your values and have sex if that’s what you want.

You can also know that, you know, if if you know for you that sex is difficult to extricate from an emotional connection, and you know the person across you want a deep emotional connection and you with a future partner, and you know that the person across from you doesn’t really want a partnership, they’re just looking for a hookup. You can know for yourself whether or not having sex with that person would serve you and your self-trust. Right? This is introducing more nuance.

through the lens and framework of self-trust so that you can make the right decision, decision by decision, for you, instead of a blanket rule, basically outsourcing your self-trust to a dating expert who is not you.

Because you desire certainty, which doesn’t supereist in the real world, like certainty of like, this rule applies here all the time. things are a lot more fluid than that. Moments are a lot more fluid than that. There’s a lot more factors involved. And I want you to build the skill set of self-trust to come home to yourself, to release fear, anxiety.

And s scarcity from your decision making so that you can come home to your self-trust and make integrity-rich decisions with your values, no matter what that is. So now let’s talk about what does this mean for you? What does self-trust mean for you? How can it help you? I want you to tune in with where you feel stress about a decision, whether it be when do I have sex with somebody or whether it be do I go on a date with this person, a second date with this person, am I into them or not?

Notice where you feel stress about this decision. Ask yourself, what do I want to do? If you gave yourself radical permission to do what you wanted, you wrote yourself a permission slip, I have permission to do what I want to do. Does an answer pop up for you? Like an answer from your body, does it come for you? Now, some people this comes, some people it doesn’t. Some people have a relationship with their body that is different because of past traumatic experiences.

And past rejection, No matter what, I just want you to breathe, listen to what I’m saying, take what you need, leave the rest. Okay. Tune in with what do I want to do? For example, you know, like, do I want to go on another date with somebody? You can ask, like, if you value co-creation and reciprocity, did this person co-create a date andor a conversation? Have I talked to them about what we’re looking for in dating?

for the sex combo, what’s my personal preference in regards to sex, knowing that there’s not a right answer that will magically fix everything? What’s my preference? Self-trust, again, is coming home to your decision making, asking yourself high-quality questions, and seeing what emerges for you. Ending the never-ending cycle of outsourcing your self-trust to other people who you think know more than you. You are the keeper of your best answers, and you better learn the skill set of self-trust now.

So that you can have a more integrity-rich life where you feel like you belong to yourself. You have agency. Self-trust is about claiming your agency of choice. It’s about being the main character. Right? Now let’s talk about the skill set, how to practice self-trust.

Let’s do the sex question as our example today. Let’s answer the question and use A C K. Ack, my self coaching tool that I teach in main character dating and main character era. Ack A C K. Remember me being silly with ac and hopefully you’ll remember it. Put it in your pocket. Put it in your phone. AA, acknowledge. Acknowledge for the sex thing. What are you afraid will happen if you have sex too early?

Acknowledge it. Acknowledge the thought or the fear. Acknowledge what rules have I ingested that are stressing me out about what is right and wrong in this scenario. Acknowledge it. Okay? Acknowledge. Then see compassion. Right? Compassion isn’t just a fluffy phrase. It is a practice that you need to practice, like stretching. You will not be good at stretching and like

Stretching your stiff body if you do it once and never do it again. Stretching is a practice of embracing healthy discomfort to become better at something that serves you. Same with self-compassion. It is a practice that you need to come back to every single day. I am practicing self-compassion all the time.

Literally all the time. Oof, Lily, like, I I I’m sorry you feel that way. You’re not alone. I’m sorry you’re struggling. This is really normal and human of you. I’m proud of you for looking at this differently. Whatever I’m looking at, right? I I I all of us struggle and all of us need self-compassion. You deserve it. Self-compassion is gonna help you build self-trust.

2014 study out of Stanford found that the practice of self-compassion is reducing cortisol and increasing resilience, two things that you definitely need to build self-trust and also build a dating life that leads to love and build anything that is worth doing in this life. You need self-compassion, okay? So compassion for that version of yourself who wants to have a right answer, that wants to know without a shadow of a doubt what what date number is right to have sex and wrong, because you want to minimize the possibility of rejection.

How human of you. I’m proud of you for looking at this differently and you know, eliminating the either or black and white thinking stress. I’m proud of you, right? You’re human, your brain is having a lot of thoughts, not facts. All of these are self-compassionate phrases that you can use out loud and often to bring yourself into the warm, buttery bosom of the practice of self-compassion. Okay. Might be a little uncomfortable. That’s okay. Embrace it like stretching. You gotta be a little uncomfortable.

To do something new here. And then K, right? A acknowledge, C, compassion, K, kind reframe. This is what this sounds like. It might be true that I can vet someone and trust my decision of whether or not I have sex with them, case by case. It might be true that I have a standard in mind of when I like to have sex with someone and the questions that I need to ask them before doing that. I ask about their STI status. I ask about their desires and intentions in dating. I ask about

You know, anything you want to ask about before sex, you can trust that you can follow your own personalized protocol to do it in a healthy way for you. And then, you know, more broadly, it might be true that I’m learning how to trust myself moment by moment, choice by choice. I think about Brene Brown talking about building trust with someone else in the book Dare to Lead. she talked about how her daughter,

Thr said, I trust my friend because she remembers your name or something like that. I don’t remember exactly what it was. And Brene Brown said in the book, like, no, self- trusting someone else is, you know, they big they do a big gesture and you see that they show up for you. And then she realized with her daughter standing in front of her that Trust with someone else was built in micro moments, micro choices.

That built on top of each other to create the experience of trust with someone else in relationship. This is why I say, you know, like interpersonally, trust with another person is built date by date, moment by moment. and you know, you get to build that trust with someone else as they show up for you, as they remember details about you, as they ask you questions that show you that they are listening, right?

It’s sort of like a marble jar, Renee Brown talks about the marble jar in her daughter’s classroom, where you know, good behavior is like a marble in a jar. You get one for every good choice you make. Trust is the same thing. Choice by choice, you’re filling the marble jar. Self-trust, if you currently do not identify with as having self-trust, then your jar might be a little emptier. Okay, that’s neutral. We are choice by choice putting marbles in your self-trust jar. So finally,

Distress tolerance, this concept. I’m using this concept that I was taught by my fabulous friend, Megan Saxelby, who is an educator and a parent coach for kids who are adolescents, age 10 to 14. She’s fabulous. Check her out. Wild feelings. she was a teacher for 15 years, and she was teaching this concept of how to break down complex topics. And it was basically like we’re gonna define the concept, then talk about what it means for you, then talk about the skill, how to practice.

Then distress tolerance is going and doing it under real conditions, evaluating and trying again. So here’s how to do this. Today, go make a small self-trusting decision, and if possible, notate it in your brain and celebrate it every time you do. Here are some examples to build self-trust. And this can also build up to making the right decision for you about when to have sex with someone, as an example.

So, small examples today. Go to the bathroom when you need to instead of waiting until you’re bursting. Try to eat when you’re hungry instead of waiting to bang out five more emails. Try to be truthful in an email or to a on in a text to a friend instead of people pleasing. Try to be a little more truthful, a little more self-trusting. Try to tell a friend how you’re doing honestly today when they ask. Try to notice when you need to move your body when it feels stiff at your desk.

All of these things are tuning in with your mammalian body and making choices that are trusting it. Instead of saying, No, I have to do this externally pressury expectation thing of banging out five more emails before I get to trust my body and go to the bathroom. Like it starts this small and this simply. After each of these decisions that you make today, say, thank you, self-trust.

Then for the bigger stuff, when to have sex specifically, you can use ACK, Acknowledge Compassion, Kind reframe, to come up with a high-quality experiment to figure out, like, okay, let me play with a few factors. What feels right for me? Instead of getting stressed out by all of the dating experts’ opinions or your family friends’ opinions, notice where self-trust can speak up and be courageous. Ask for like the sex question. you can use this self-trusting framework to you know, ask someone out.

To flirt, to make the first move. Self-trust, again, the psychology today definition, it doesn’t mean that everything’s gonna go perfectly your way all the time. It means that you will have your back no matter what happens, which is really all that we can do in this life. We’re not in control of the outcome. So all we can do, all we have control over is how we treat ourselves, how we shoot our shot, and then how we treat ourselves afterwards.

This is a framework for trusting yourself instead of feeling like you have to follow somebody else’s plan for you by the letter. This is a plan to build your agency instead of outsourcing your trust to someone else who you think has the best plan for you. That’s why in my programs, we are focusing on building your self-trust. So you have a framework to live your biggest, boldest life, whatever that means for you.

Because you are the keeper of your best answers. You are the expert of what you want and need. And you just need to shed the shit, the shoulds that are clouding your self trust. I should do this person’s rule. I should do that thing in dating. I should want this and that and the other. But I really don’t. I really want to do this other thing, but it goes against what this dating. Okay, trust yourself. I love when my clients come to me and they say,

I actually like trusted myself and the dating app that we chose for me wasn’t working. So I trusted myself and I pivoted and I’m doing this other thing that you didn’t necessarily recommend, but that I felt was right for me. I say, hell yes. Right? I want you to trust yourself over listening to an arbitrary set of rules that may have worked for other people, but may not work for you. Now, there are guidelines that you can resonate with and adopt in your self-trusting framework, but

I really in this work want you to acknowledge that this is deeper than just dating. This is deeper than just sex. This is how you listen to yourself and how you make decisions based on what you want and need without scarcity and fear making decisions for you. So go trust yourself today, little bit by little bit, and then celebrate it. You’ve got this and I’ve got your back. Talk to you soon.