You know that spiral where you replay a conversation for hours, convinced you said the wrong thing to the wrong person at the wrong time? Lily’s got one sentence that ends it.

This week’s Episode Spotlight revisits the piece of advice that went viral for a reason: you cannot say the wrong thing to the right person.

Inside this episode:

✨ The exact moment on a first date Lily talked about her ex for 30 minutes straight, and why it didn’t end the relationship (it’s the one she’s still in, eight years later)

✨ The follow-up nobody talks about: the right person isn’t just forgiving, they know how to ask for what they need

✨ Why “minimum viable audience” means you’re not for everybody, and that’s the relief valve for first-date anxiety

✨ The difference between being a mind-reader and letting someone tell you what they need

✨ How to stop treating dating like there’s a secret script you have to get right

Work with Lily

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A feminist guide to breaking dumb dating rules and finding love. Order HERE

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Show transcript:

Lily @ Date Brazen (00:37)
Hey, gorgeous friends. I’m so glad that you’re here. So I’m pumped for this episode because I’m giving you my hottest piece of dating advice that consistently goes viral. Consistently, people say it relieves them from so much dating worry, dating stress, dating overwhelm, which is what you deserve. Okay. Cause I know that dating is a microcosm of every hope, joy, dream, fear, insecurity, desire that you have as a human. And as such, dating matters to your well being.

So I want you to date, and I’m here to help you date in a way that feels like an act of self-care, that actually enhances the quality of your life, believe it or not, that actually is joyful. And how is that possible? Or why does that even matter? Because dating is an expression of your agency. It’s an expression of your desires in this life. Desires are your birthright. So I want you to go after what you desire in a way that is aligned with how powerful you are.

How full of agency you are, how r resourced you are. I mean, this piece of advice that I’m gonna give you in this tiny little sentence that I’m about to say is going to unlock a lot of that for you. Because right now, I would imagine if I know you, which I’ve coached a lot of people on this same subject, so much so that when I talk to my clients, they’re like, wait, how did you get in my brain? And I’m like, Because everybody has the same questions and worries. One thing that I I know about you is that you probably are worried.

You’re probably worried that you’ve said the wrong thing in the past, or that you messed up the right thing in the past, or that what you wanted, this relationship that you deeply desire has passed you by, that you’re too late, ⁓ and that you’ve said the wrong thing, or that you’ve done the wrong thing in this life, right? To mean that you’re here and you’re single and it means something about you. Okay. If I know you, I know that you probably had those thoughts. I’m here to tell you the one piece of advice that is going to free you from so much of that dating worry.

Is that you cannot say the wrong thing to the right person. I’m gonna repeat that. You cannot say the wrong thing to the right person. And I’m gonna unpack how why that is. ⁓ I’m gonna talk about your like, but Lily, what ifs? I’m gonna get there. But this simple piece of advice, it changed my life because I ⁓ worry, okay? Something about me, I have social anxiety and I have.

Overthought things that I said years ago for hours at a time, years online. Like ⁓ I’m a a textbook overthinker and I’m working on that in therapy. Both and I knew from a couple of my relationships in my life, I just noticed that when I allowed myself to say the thing, ask for the thing, ⁓ talk about the thing with them, whatever it is, a vulnerable conversation.

With the right people who are in my life today, it always turned out okay. It always turned out okay when I asked for or said what was on my heart and mind. Let me give you the perfect example for your romantic life. So I was going on this first date with Chris and I was really nervous and I was a little bit late, a lot late, and I show up and we have this really fun like connection right off the bat.

we have great chemistry, great vibes. I’m attracted. He’s attracted. I can feel that. We’re laughing. The conversation is pretty easeful. I’m feeling awkward, of course, because it’s a first date. And I’m like, this is going really well. Like, but I I wasn’t in my head. It was just really, I was really present with Chris. Now, cup maybe an hour into the date, I he asks me a question and I just start talking about my ex. Now, looking back, wouldn’t recommend this.

I wish that I had doubled up on therapy that week instead of going to this date ⁓ unprocessed with a couple things with my ex in that breakup. And I was present, I was there. He asked a question. I answered, I started talking about my ex. I talked about my ex for about 30 minutes. It’s not a good look. Okay. And Chris, to his credit, held my hands, asked me follow up questions, listened, said, That sounds hard. And then we moved on.

with our conversation. We are now seven, almost eight years into our relationship. I could not say the wrong thing to the right person. And I use that example because it’s a pretty classic one like don’t talk about your ex on a first date in in in a really long way or whatever. Again, wouldn’t recommend it. And I couldn’t say the wrong thing to the right person. The important follow-up here that I think a lot of people miss in this conversation is the follow-up about

Boundaries and the right person being able to set boundaries. Because inevitably I hear in the comments like this, like literally this video about you can’t say the wrong thing to the right person has gone viral on Instagram, which is so wild. I’ve never gone viral on Instagram. Like two over two million people have ⁓ watched this video about you can’t say the wrong thing to the right person. And in my comments, I see consistently this like, but Lily, if I say something

that ⁓ that is rude or that offends them, then I will have said the wrong thing, right? So this isn’t true because whatever. Now, if you’re saying something rude or hateful or like really out of alignment with what I hope are your values as a human being of kindness and and compassion, then maybe that’s not the right person for you. Maybe you’re not at the place to be in a relationship. Both and if you say something that like again wouldn’t repeat it, wouldn’t

recommend it. Like I was talking about my ex for 30 minutes on this first date. The important follow-up is about the right person as an adult who can set boundaries. A couple months later, Chris, because the ex thing kept coming up, because I was still processing, I’m a verbal processor, right? And you can’t say the wrong thing to the right person. And when Chris was done here, like when he was like, I don’t want to talk about your ex anymore. I really want you to talk about that with your therapist or your friends. Can we just focus on us and our new relationship? He was able to say that to me.

The right person. I remember where I was when he asked me to like process that elsewhere. I remember the street. I was in Hell’s Kit. We were in Hell’s Kitchen. I think we were going on a date or we were coming from a date. We were walking to or from a restaurant. I remember like the block number. It was like 44th and 9th. And I remember him turning to me and saying, Hey, Lily, I really I I hear you. I know you’re going through lot. Can you talk about that?

You know, with your therapist or your friends. I really want to focus on us and our new relationship. And in that moment, I was like, holy shit, he’s so right. I’m so glad. I felt embarrassed. I felt a little ashamed, but I was also so glad in that moment that he felt comfortable being honest with me. And I was like, ⁓ adult communicator communicating his needs with me. I don’t have to mind read. He’s gonna tell me what he needs, right? And I’m going to process elsewhere now. I’m a human being.

Who makes mistakes and who does things they wouldn’t do again. That’s just normal human being behavior. And he was being a human being, ⁓ asking for what he needed. And that is a an adult relationship. Two human beings coming together in a messy way, like not messy as chaotic, messy as like imperfect, and communicating and asking for what they need and and moving on with their lives. Okay. So that is why you can’t say the wrong thing to the right person.

That’s why you can release yourself of any of that self-blame about I asked them out too early, or I shouldn’t have asked them out, they should have asked me out, or I I shouldn’t have asked for a relationship so soon, or I shouldn’t have said on a first date that I wanted kids in the next three to five years, like whatever it is, you cannot say the wrong thing to the right person. Here’s another follow-up that’s really important that hopefully frees you from so much worry and anxiety. The right person will ask. What do you mean by that?

The right person will ask for clarification if they need it, right? Because the right person is also interested in being in a relationship with the right person. The right person for you is also doing their work to be in a good relationship in the future. That’s why I think like when people talk about, especially women who date men, when women who date men talk about like, ⁓ men don’t do their work, men don’t go to therapy, men aren’t.

Men aren’t interested in improving themselves, whatever. I I just say, like, yeah, a vast majority are not. Like men were not socialized to do emotional work like women who were social women or people who are socialized as women. Both hands. I’ve seen enough to know that those men do exist. Yeah, they’re they’re in smaller number than those who are not doing their work and learning how to communicate and learning how to be emotionally mature and ⁓ and and and emotionally literate, right?

Those men are doing their work and they exist and they’re fewer than the masses, and that’s okay because another one of my pieces of advice that I say all the time, you are for the few, not for the many. Minimum viable audience. Seth Godin is this marketer who I love. He is very prolific. And he talks about this thing called minimum viable audience, the smallest number of people who would be right for you that you need to start looking for and speaking to and setting boundaries to find.

Because they exist and you’re not for the many. I learned this ⁓ starting date brazen because I was so anxious and I was in deep scarcity mode seven, almost eight years ago that I started Date Brazen. Yahoo. And I was so anxious that I would never ever find a client that I would go out in the world and be like, anybody, like come come be my client, come work with me. Anybody who’s single, right? It didn’t work out. I didn’t have very many clients. I was anxious as hell. I was in scarcity.

What when that changed was when I adopted the minimum viable audience philosophy, when I identified the smallest number of people who would be values aligned with who I am and the work that I want to do. Right. I worked I worked on like, I want to be a feminist dating coach and I want people who identify as feminists and are striving to be intersectional. And I want people who don’t want a relationship to make them whole, but who want it

and who want to celebrate themselves as they are right now single, right? Like identifying the the few people who would be right for me led to actually me talking to those people and and f in the future working with them and attracting them into date the date brazen universe and like helping them even better than I could go after like the many and like try to help people who may not be ⁓ the right fit values wise.

Same same with your love life. That’s just like one example of how minimum viable audience can really free you from the scarcity trap because you’re not meant to be with for everybody or with everybody. You are meant to like ⁓ know what you want first, ask for it out loud and often, get messy, share things, get awkward, be human about it, set boundaries when you need to, bless and release when you need to. And that makes the right relationship inevitable.

My gorgeous friend.

Period. So you cannot say the wrong thing to the right person and you are for the few, not for the many. This assumes that you’re human and that everyone that you’re gonna date is also human. This assumes that there’s no such thing as perfect conversation and perfect connection. It is always imperfect and messy and human. And ⁓ it’s assuming that that’s okay. That you don’t have to hold yourself to a perfect standard in communication in order to find the right partner or partners, right?

The the implicit the implicit assumption that I think people are making when they are pressuring themselves to say the right thing in the right order at the right time always is that there’s a right order to hook ⁓ in in order for a relationship to happen, implying that there’s some game afoot that that you have to play perfectly in order to find love. The idea that you need to hook in with the right order of things and the right ⁓ you know, ⁓ the saying the right thing at the right time.

It’s assuming this this game that doesn’t exist. Now, ⁓ as a both hand, engaging the complexity of this and the nuance of this, there are questions that you can ask somebody deeper into knowing them when trust has been established, right? That you may not want to ask upfront. ⁓ this doesn’t mean that you have to ask or say everything that you want to know in a relationship at the first date. That’s anxiety about like things I’ve got to figure it out now, so blah, blah, blah, blah, blah.

Yeah, there are things to figure out on the first date. That’s the qualifying, disqualifying questions of it all. Episode 182 of the Date Brazen podcast outlines my entire qualifying disqualifying question strategy, as does my book, Thank You More Please, so that you know like what questions I recommend asking before a first date, on a first date, second, third, fourth date, and onward. In this new relationship that you’re building, you’re building trust. And as trust builds, the depth of conversation, the depth of questions that you might ask also will build.

You can ask anything. You can’t say the wrong thing to the right person. But just know for yourself like what would I want to ask on a first date, on a second date? Know for yourself what feels important for someone to know about me and how can I open up about that. ⁓ not in a, I need to tell them that I have never been in a relationship upfront because they’re gonna think that’s weird and they’re gonna release me unless they’re someone really special and I gotta right, like know your body, know your anxiety, and give yourself permission, like

The right person will not be freaked out by what I have to say. They’ll ask a follow-up question. The right person ⁓ will be curious about me. The right person I’ll be curious about them if it’s the right person for me. The right person will make themselves apparent. I don’t have to do all of the emotional labor of figuring out the exact order of operations for what questions to ask when. I can just show up, know what I want to know, know what I want to ask, know what I want to share, and go from there.

Get messy. Be imperfect. Be human. Give yourself permission that you cannot say the wrong thing to the right person.

And if you’re just getting started in this date brazen universe, my book right there, Thank You More Please, A Feminist Guide to Breaking Dumb Dating Rules and Finding Love, is available. Everywhere books are sold. And you can ⁓ read it and DIY this gorgeous, joyful as fuck dating life that becomes a magnet for the right person. ⁓ and I have a bonus for you if you get the book at date brazen dot com slash book.

Get the audio book or the ebook or the hardcover book and start creating the love life of your dreams that becomes a magnet for the right partner right now. Because your desires matter. What you want matters. You want something that’s not here yet, so let’s fucking go.

What you want is possible. And you can borrow my belief at any time. I’m over here in Brooklyn believing it for you until you can believe it for yourself. Talk to you next week.