Joyful Dating with Feminist Dating Coach Lily Womble
- Erin Keating
- 1 day ago
- 37 min read
Erin: Welcome to Hotter Than Ever, where we uncover the unconscious rules we've been following. We break those rules and we find a new path to being freer, happier, sexier, and more satisfied in the second half of our lives. I'm your host, Erin Keating.
Welcome, welcome, welcome, listeners, new and old. New listeners, I'm so glad you're here. Here, however you found us. Maybe you heard me on another podcast and thought, hm, I liked her point of view. Or you saw something on social media, or maybe you came across the full episodes that we've started to drop on YouTube. I'm so excited to be getting the full video episodes up on a different platform. Everyone's saying the future of podcasting is video. The future of radio is television. Everything old is new again and we are here for it. Maybe a friend shared an episode with you and said, oh, my God, you have to hear this. This is for us. However you got here, you are in the right place. Welcome to you and if you are a loyal listener who tunes in week after week, and I know there are a lot of you who are devoted to these conversations about how we can have new options and choices to do things differently and more authentically for ourselves in the second half of our lives.
To those of you who look forward to Thursdays, when new episodes drop every other Thursday these days. I'm so happy you're here, and I'm so happy you're here for this amazing conversation with Lily Womble, my guest today. Lily is a feminist dating coach. Who knew there was such a thing? I need a feminist dating coach. I am a feminist. I need a feminist dating coach. She is a feminist dating coach, an author, a speaker, and the CEO and founder of Date Brazen, which helps women to build joyful dating lives that lead to extraordinary love. Who does not want extraordinary love? I know I do.
She's the host of the Date Brazen podcast and author of the bestselling book, "Thank you More Please: A Feminist Guide to Breaking Dumb Dating Rules and Finding Love." Lily and I met through a mutual friend, and as you will hear in this episode, it was definitely a love fest because Lily acknowledges the challenges of dating today and helps people like you and me navigate this experience with authenticity and integrity. And what I love about her is that her approach is so real. She said something that has resonated with me over and over again that I now applied to my own dating life as I've been trying out dating in a different way. Still looking for lovers, but also being more open to that big love, the real relationship and partner who might be a fit for my very complicated life and psyche. We all have a complicated life and psyche.
I'm here to tell you someone who will fit into my life as a single mom and person who is in the midst of a full life reinvention. I believe that there is someone out there for me. And she said, "you can't say the wrong thing to the right person." You can't say the wrong thing to the right person. I love that. And it really sets me free. When I am talking to guys online, when I am going on dates, I feel totally liberated to be my authentic self, to not have to be so strategic and feel like I have to game things out. If the person you are talking to is going to be your person, you cannot scare them away. I love that message. She drops this and so much other wisdom in this conversation. I can't wait for you to hear it. All right, let's get hot.
Lily Womble, welcome to Hotter Than Ever.
Lily: Erin, I'm so glad to be here.
Erin: It is so great to have you here and it is so great that you have such an optimistic take about what is possible in dating because I don't think women hear that very much.
Lily: No, and for good reason, right? Dating, I think, is stuck in patriarchal dark ages, especially the way that we were taught to date women and people socialized as women. I'm from the deep South, so like I was raised in the of, you know, a woman's worth is higher when she's in a relationship and when she's single, it's lower, she's behind in life. And it's what I think we all were taught implicitly from a young age or explicitly from family members. Right? And then if we think about, you know, the, the historical legacy of women not being able choose for themselves whether they want to be single or coupled, choose for themselves who might be the best partner, choose for themselves the timing of partnership or, or babies or whatever. Like it's pretty recently that women had that power of choice. I mean, wasn't until it was like a little more than 50 years ago now that a woman could get a credit card without her husband's or father's permission.
So it's just one example of like, of course the way we were taught to date is stuck in this old paradigm of women need to shrink in order to find love. And so I'm all about interrupting that shit and making dating this like agency filled, joyful, as place where women can express their agency and power and ultimately find the right partnership.
Erin: Oh, my God, Lily, there's, like, so much to unpack here. We just went back to, like, when women's white rights have been granted and the impact of the patriarchy on our romantic expectations. Like, there is so much here. And because this podcast is for women over 40, I think the Gen Xers among us, like, you know, we were the first generation raised by feminist moms. And so what was modeled for us is so interesting because, I mean, in my own experience, my mom was dating when I was young. And so what I was watching was the reaction to her marriage, the reaction to her divorce, the reaction to her own, like, agency in the world that she was finding for the first time along with a whole generation of women. And then how does that trickle down to us in terms of what we're entitled to expect and this. This moment in time that we're in and the patriarchy is having. Is having a moment, sure.
Lily: Hopefully a sort of a last dying Golem on the shores of Mordor breath, but it's a tough moment, for sure.
Erin: I certainly hope that you're right about that. They are not going gently into that good night. They are fighting feminism and the impacts of our empowerment and the way that women's roles in society have changed so tooth and nail. And it's really challenging to be a woman who is attracted to men and who dates men and who's interested in men who, like, you know, who wants men in her life. I hear a lot from people who listen to this podcast that it's not worth it, and I don't feel that way. I don't feel that way. I want love, I want connection. I want sex, I want relationship. I just think, like, I want to hear about how we do it differently now, especially for those listeners who are feeling like, I want this, I don't know how to do it.
Lily: Yeah. I mean, I've got some tactical solutions that we can talk all about. You know, my book, I think it's like, equal part mindset work and tactical strategy for that reason that, like, you know, there are ways to figure this out and do it more joyfully with more boundaries and more agency in the process. I also, you know, started where I started because I don't want to. I'm not Pollyanna about this. You know, like, I'm not sitting here saying, let's build a joyful dating life because just because this can be fun it's like, no, you want something. I believe that dating is a microcosm of every hope, joy, dream, fear, insecurity, desire that we have as humans. I think that if you have a desire for the right partnership, that dating needs to be and can be an act of self care because.
And it's, it's an expression of your desires, which, you know. Dr. Juliana Hauser, who you've had on this podcast, says that desire is your birthright as a human being. So I just want to envelop everybody who feels like I want the right partner, but it doesn't exist. I want to give you a big hug and say, like, you get to have your feelings. You know, like those feelings, those thoughts make sense in the context in which you were raised and in which we're living right now, both and centering.
Erin: Thank you. Yeah. I want to embrace that permission to have what I want. Because you talk about not settling, and I think so many of us feel there's just like a lot of opportunities to settle, a lot of opportunities to settle.
Lily: If you're going to be given 10 opportunities, eight of them will be to settle. You know, it's like, I think that that's why I say you're for the few, not for the many. You know, this concept of minimum viable audience or minimum viable market from Seth Godin really changed my life when I found it. Do you know of this concept?
Erin: Yes, but please share with the audience.
Lily: Yeah, so Seth Godin says, marketing expert, very business-y guy, great vibes. And I was building my company Date Brazen seven years ago, and I was freaked out. I was drenched in scarcity. I had just quit being a matchmaker at a national firm. I was the third most successful matchmaker at that company setting. Yeah, I'm an open book, left, right, and center setting up dates. And my own dating life was a dumpster fire.
You know, the way that I know the tools that I teach now work is because I was my first client. You know, once I found the courage to break up with this toxic relationship where I was settling every single day and putting my needs so far in the back of a drawer that I couldn't get to them. My therapist helped me break it off, and then I was like, but now what? How do I never settle again? So these tools are, you know, what I learned helped me release the story of I was too much for myself, really engage my needs with self compassion, start flirting IRL and shooting my shot. Because self compassion just helped me through rejection and helped me build resiliency in the face of vulnerability. So I was starting my business, I knew that this feminist, these feminist dating principles worked in my life and in the life of my matchmaking clients. But I started this business, I was like, I have no idea what I'm doing.
Nobody wants to work with me. Everybody is so overwhelming, the market is saturated. And I went out in the world, I said just anybody who's single, work with me. I had one client in my first whole year of business and then I learned about minimum viable audience which says that you need to just define the smallest number of people who are right for you, who are values aligned, who want to go where you're going, who are into what you believe. Define that smallest number of people, that's your minimum viable audience. And you are for the few, not for the many. In that way, when you start talking to and searching for the few people who are right for you, that's when you're going to start to find success. When my business started taking off and I started applying this concept to my clients love lives and that's when I really helped people define the smallest number of people.
The right aligned fits who are subtle proofed right. With essence based preferences. Because I think that most people who are dating are going to be wrong for you. And I think the idea that all men need to be right for you if you're into men is a fallacy and false. Most men are wrong for you, if you date men. And identifying your essence based preferences, meaning.
Erin: How you dig into that, like what does essence based preferences mean?
Lily: So most people do one of two things. They over function rigid checklist. Must be this tall. Exactly this location.
Erin: Right, right.
Lily: That's in an effort to self protect the other half of human.
Erin: Wait, I want to slow you down because everything you say has so much to it. We create these criteria because we think we know what it is we need to be happy and successful in a relationship. But those checklists can be very rigid. And so what do you mean it's an effort to self protect?
Lily: Well, I think that the idea that like I know what I need, I need this, this, this and this and this job, this exact salary. This location, exactly. This height, exactly. This age, exactly. It's not that you necessarily know what you need in a relationship, it's that you want to protect yourself from being with the wrong people.
And so you've learned, you know, to get. Because you're maybe afraid because someone might be afraid of being in the wrong relationship again, they're trying to like avoid it. So they're trying to think like, okay, how can I really game that game? And how can I really protect myself from being in the wrong relationship? Oh, I know. Rigidity must be this tall to ride. And what that does is it gets you in good on paper dates and relationships that don't feel good on the inside.
Erin: When I met my husband, I met him online and I had given myself a project. Now ex husband, I had given myself a project which I was going to go on 10 dates and I was going to probably fail and then never did again. And he was number five and I went on six. Number six was a Harvard triathlete who was a, you know, in finance who was perfect on paper and who I hated in person, who was so pressure-y and asked me what my first impression of him was within 30 minutes of the date. And I was like, I'm still having that first impression and this is now part of it.
And then I looked back at the date from the night before and I was like, that guy was pretty nice and we had a nice rapport and, you know, but I understand wanting to take it on as a project. And that guy, number six was right on paper. Number five was what felt right, right to me. Even though he didn't have all the things number six had, you know, my body told me information about how I felt about him. My brain sparked when I was with him and we made it 17 years.
Lily: It's a long time.
Erin: It was a long time. And it was over, long before it was over. But, you know, I have beautiful kids and we built a life and all of the things and then sometimes it just doesn't evolve with you. Right? But the right on paper, that was my right on paper lesson. Like this dude was, you know, number six was like fully right on paper, but not right in reality. So I'm really resonating with what you're talking about.
Lily: Yeah, I mean, that's the essence based preferences. Someone's essence, I think, is how they, how they make you feel, how they inspire you to feel in person. From their values, from their, their, their personality, how they act, how they, how they're generous in person or not.
Erin: You know, for me it's like all communication. I have casual relationships with several different guys currently, and I like them all for different reasons, but none of them are boyfriends for different reasons too. I'm doing it differently than I've done it before and one of my guys who I'm crazy about like really did not show up for me during the wildfire fires. And I was like, okay, that's interesting data about this person that like he's capable of doing certain things but not other things. And I just realized like how critical caring communication is to me, especially when I look forward to it to having a more like three dimensional, robust, non casual relationship with somebody, you know.
Lily: Yeah, I think that that's the feeling what I'm hearing is like safety, you know, and like if I, you know, pop this ball in the air, are you going to catch it, you're going to throw it back and in these different scenarios, like are they game to connect and make me feel, do they make me feel safe? Do they make me feel seen? And I think that's what is important about moving from the good on paper over functioning to the middle of these two polls. And I could talk about the under functioning as well, but the, the middle is essence. Like how do you want to feel in the right relationship? I had a client who really needed, you know, she said I need someone with a graduate degree, period. Like I need someone with a graduate degree.
Erin: Because she had one?
Lily: Well that's the thing is like I was asking her about it and I think it was veering and over functioning because I could you know, send her 10 people. Not that I was matchmaking but like if I had sent her 10 people with a graduate degree, that's not a, a good qualifier disqualifier. So I asked, what are you hoping a graduate degree makes like means about somebody? Yeah, well they value education. And I was like, okay, deeper. What do you, what do you hope that it leads to? I want my dad to be impressed with the person that I choose because he's never been impressed by my boyfriends. I haven't had very many. And he was so rigid about wanting me to get a graduate degree. And so then we like helped her shed her shoulds of like what were the on paper things that she thought she needed when in actuality she could date somebody without a college education if they were really intelligent, very witty and curious and reading all the time. So those like that feeling of inspired by their intellectual curiosity is, was one of the essence based preferences that we came up with together.
Erin: I love that. But you really have to be willing to look at yourself and to get underneath who you're doing things for and what you're trying to get out of it. Because we think, oh, we're just going out there to meet someone who will be, you know, our best friend and lover and you know, all the things, all the things and we're trying to fulfill through relationship. And I don't know that a lot of us have ever really interrogated like what makes me feel right.
Lily: Yeah, well, and that's why I think that a light, a life changing moment for your love life could just be being asked the right questions. Right.
Erin: That's why I love any fucking questions.
Lily: Any questions.
Erin: Monologue. Sure, turn off the monologue, bro.
Lily: Yeah, and the right people, right? That, that's a good qualifier, disqualifier as well is, are they co creating the conversation, are they co creating the date or are they steamrolling or are they completely taking a back seat?
Erin: Right.
Lily: That's the under functioning is the opposite way that a lot of people swing from over functioning, which is under functioning is I just want somebody nice and funny, right? Or like I just want somebody with a job who can pay his bills and, and is nice to me, you know, that, that like wanting nothing or wanting the bare minimum because of scarcity, because of past trauma potentially. And wanting too little also will mean settling.
Erin: How do you get out of a scarcity mindset? I think I have a scarcity mindset when it comes to like I'm super happy to have lovers. Like for me, like having a handful of lovers who are available in different ways at different times, like I don't really have to expect too much of them. Like it doesn't have to be high stakes. Like that's what's been working for me in the first couple of years of separation and divorce. But I'm starting to feel like, okay, like I could actually have like a three dimensional like full life integrated thing where we know each other's kids and we do all the complicated shit, right? That's terrifying for me because I've always failed at that. Even in my marriage, I felt like I was failing at relationship all the time. And, and, and also like reinventing my career. I feel like it's really hard to get out of a scarcity mindset where it's like, how am I going to build the opportunities I need? Like, oh my God, look at my bank account.
Like all that stuff is so no matter how fucking incredible and empowered and whatever that I am, I still have that underlying stuff. Like how do I get, how do I. I mean, I have a therapist, I have all the things. But yeah, how do I work? I work on all of it. But like in dating specifically, how do I give myself permission to have higher expectations.
Lily: Well, I think what I'm hearing is a lot of, if I may.
Erin: Please, please. I put myself out there to grow.
Lily: Thank you for sharing, I think it's so relatable. And I think I'm hearing a lot of, like, self judgment as protection. I see feelings.
Erin: Oh, I have feelings.
Lily: Very normal. And I'm also hearing grief. I'm not where I thought I would be.
Erin: Right.
Lily: Or I'm not where I wanted to be or whatever the sentence in your head is when you have looked at your bank account, as you mentioned, or whatever, you know, like, there's big feelings there too.
Erin: There's big feelings everywhere. Yes, I have a lot of feelings.
Lily: Yeah, you're in tune. And I think that the way through it, you know, I love the work of the Nagoski sisters. They're great. They wrote the Burnout and the book. Burnout is about the idea and the fact that burnout is caused by disengaging from our needs. And why do we disengage from our needs? Because there are feelings and stress cycles that are left unprocessed in our lives all the time. And the way that we process a stress cycle, they give very tactical advice for this is by giving ourselves permission to feel our way through the feelings.
They say feelings are like tunnels. Our job is to feel our way through the darkness to get to the light at the end. It may only take five minutes of, like, I have permission to feel this feeling of shame. Like, one of my favorite sentences ever that I use every day is, I'm willing to feel anything to be with you. There's nothing that you could say, do, or feel that would make me want to stop being your friend. Coach Simone Soul taught those to me, and that really helps me, like, give myself permission. And I'm offering it to you too. Just, like, permission to feel this for three to five minutes. Where is it in my body? What color is it? What shape is it? Using the tool of emotional granularity to, like, name it and see it and allow it, instead of being like, shut up. You're so inconvenient.
Erin: Oh, yeah, yeah. And I think a lot of us were taught that as kids, right? That our feelings were not welcome because they are inconvenient. And they threw a wrench into the works of however our, you know, family systems were set up.
Lily: I think that another piece that it, you know, feelings are not facts.
Erin: Yeah.
Lily: They're guideposts. Their information, their vibrations in our body. The feeling of hopelessness is a feeling, not a fact. And so what if you just allowed yourself to feel it? That. That. That is like one of the pieces. I use this tool in my work called soft S O F T and I just came up with this acronym to help people move through hopelessness into greater hope. And it's "S", Self compassion. So just like poor baby for this, I'm sorry you're going through this. Of course you don't believe that what you want exists romantically. You haven't had it yet.
Erin: That's right.
Lily: Of course you are unsure what to do with your career. You haven't had your dream career yet or whatever it is for you.
Erin: Right, right.
Lily: Makes total sense. Of course I'm struggling. I'm here with you. I'm not alone. "O" own your needs. What if on paper you wrote down five things that you need in this moment to triage support for yourself? I need to text my therapist. I need to go on a walk. I need to move my body in some way joyfully. I need to lay on the floor, like, whatever it is. Owning your own needs right now.
"F" feel your feelings. What I was just talking about with like, where is it in your body giving yourself that permission, Setting a three minute timer and just like, allowing that feeling to be. And then t. Which is the like, action step of it all. Thoughts, not facts. So these thoughts that you're having, can you give me an example of a dating thought that you're having that you wish you didn't have?
Erin: Yes. The guys who will treat me well are too Beta. I won't be hot for them, so just distilled.
Lily: They don't exist.
Erin: Yeah, I don't. The person who I imagine will combine all the things I need, doesn't exist.
Lily: Yeah, doesn't exist. That's a hard human thought. So you'd go through, like the SOF with that thought. And then once going through that tunnel, some light, some space would emerge if you could go, you know, imagine it with me. We're not gonna do it right here. But thoughts, not facts. What's a baby step? Reframe. Not going to the aggressive toxic positivity opposite of like. It is possible.
Erin: It's going to whatever, get rid of those negative thoughts.
Lily: No, that's actually like, terrible advice.
Erin: So bad.
Lily: Because the brain's just trying to like, protect itself with those thoughts because vulnerability is very, very scary. So what else might be true if I gave you the sentence starter? It might be possible that or it might not be impossible. That does something come to mind or shall I share what I go ahead and share? You haven't met everyone yet.
Erin: That's true.
Lily: There are still friends you might meet in this life. Right?
Erin: For sure.
Lily: So it might be true that you haven't met every man who you might be connected to in this life who might be aligned or not. A baby step. You might not know everything.
Erin: Yeah. Believe me, I know less and less every day. I agree with you and I really feel like the challenge for me and women like me who are hyper achieving, used to getting it done, used to being able to manifest things. Like I know a lot of women who can do the life part of their life, but not the love part of their life.
Lily: Yeah.
Erin: And the challenge, not the challenge, but the opportunity for me is to say what is possible. I don't know everything. I don't know everyone. And I know that if I can imagine it, then it is possible. Right, I just have to cultivate an openness in myself to being willing to receive those experiences.
Lily: To learn something new. I heard you say earlier, if I, if I may offer, like you said, I always failed in relationships.
Erin: Yeah.
Lily: And I would just offer like words or magic wands. And the word always is untrue. You have in the past, fill in the blank or it has in the past not worked out, whatever. But like really watching the language with which we use to speak about this subject especially be. To open up even a teeny tiny sliver of a window of possibility. And then how do you build evidence that it is possible? I really recommend my thank you more please challenge for that, which is the, you know, the title of my book is thank you more please. It's this idea that, that, that what you pay attention to amplifies. And if you're paying attention to dating is trash. Men are trash, everything is trash.
Erin: Right.
Lily: Then you're going to get that confirmation bias evidence all the time.
Erin: Totally, I agree. And, and to be clear, that's not how I feel like, I don't feel dating is trash. I don't feel men are trash. But I do think, I do think in the echo chamber that is the Internet too. Like there's a lot of reinforcement of like, men are up in this way. Men are doing this wrong. We're right, they're wrong.
Like, it's very oppositional. It's very polarized. And I think there's a conversation among women who have potentially done all the things, quote, unquote, right and come out the other side and started to think they wanted to make some changes because it isn't really right for them and they can't figure out how dating, relationships, love, like how it could possibly work. I just think there's a lot of conversation about it. Yeah, I'm good. I'm good. Me and my girlfriends are gonna go do XYZ, which, like, totally great choice if that's the choice you want to make.
Lily: I agree, I'm not like being single, like, being coupled is not the gold standard of human existence.
Erin: No.
Lily: You know, we need to be in community with one another as human beings, as the animals that we are. And that can look like a ton of different things. Both. And if you do acknowledge that you have a desire for the right partnership, I think it's about holding the both and of I am whole right now.
Erin: Yeah.
Lily: Single, I do have a vibrant life and I have a desire for the right partner. And I'm willing to figure out a different path to finding them than I was taught. And so I do think that, you know, I think of my client Shelley, who, you know, gave me permission to share her story. She's in her 50s. She started working with me and by the way, I have a job because most women were taught how to achieve. But dating is this like one place. And why? Because of the way we were steeped in patriarchal conditioning that causes women specifically and people socialized as women to shrink.
Erin: Right.
Lily: That's why I have a job.
Erin: It's normal.
Lily: Let's figure this shit out. Like, what do you want? Let's go for it. So Shelley's in her 50s. She came in, she was widowed and she was a widow and she was a caregiver full time for, for people in her life and her family. And she had settled after her partner passed in like situationships. And what we did, we did this work of like acknowledging her essence based preferences, recentering herself, de centering the men who were wrong for her and whether or not she believed that what she wanted was possible. We also did a thank you more please challenge of like Shelley this month. Your job is to go out in the world and look for tiny slivers of evidence that the man that you want exists.
And whenever you see acute flirty interaction. Thank you more, please say it out loud. Tell your brain like it exists just in tiny slivers. And of course, do the SOFT when things get tough. That bow band, the one tool that changed Shelley's trajectory in her love life. And now she's in this loving, committed relationship with an amazing man who was also in his 50s. The one thing that changed was when she used qualifying disqualifying questions.
Erin: Okay, tell me what that is.
Lily: So these are the questions that you might be fearful of asking for. Fear of being too much or fear of coming on too strong, whatever the fuck. These are questions that you need to ask to gauge whether or not somebody has your essence based preferences. So in my book, "Thank You More Please", I give a list of 50 qualifying disqualifying questions organized by preference. I'm so type A that you could use to vet someone within like one to three questions on a dating app or in person that you can offer to your friends if they want to set you up. They need to answer these questions and their answer needs to have this vibe, is this tracking?
Erin: I'm dying for the examples.
Lily: Okay, great. So I recommend opening with the question what's bringing you joy lately? Because joy is connective. Even if someone's having a rough time, like for example, during the wildfires, if you might not want to be asked that question all the time, that's totally fine. But like if you're connected to, you know, my kids are really the joy spot in this really shitty time.
If you know how to tune in with your joy, you know how to care for yourself. Which says a lot about a person's development, about a person's ability to connect with themselves and other people and their.
Erin: Self awareness if they can answer that question.
Lily: Question growth, mindset, potentially.
Erin: Right.
Lily: Like so it doesn't matter. You're not looking for a rigid response, you're just looking for awareness in that answer or gameness. It could be a silly response, but if it's meaningfully silly and not just like lol, nothing, that's a blessing, release. If someone answers that question, like, I don't know, release
Erin: That's so Southern. Bless his heart. I'm sending him on his way.
Lily: I am from Alabama. Yeah, it is pretty Southern. But if something happens, like if someone doesn't answer that question, bless and release. If someone answers the question but doesn't ask you a question back, bless and release. If someone answers the question, release.
Erin: Sorry, I'm obsessed with this. Bless and release is kind of a nice way of saying go fuck yourself.
Lily: Bye.
Erin: Bye. See ya, I wouldn't want to be ya.
Lily: And it also can be helpful framing for people that feel guilty. Saying no to somebody nice but they're not attracted to or something, you know.
Erin: Yes. No, it's great. It's great.
Lily: Go find who is right for you. So if they don't answer, bless and release. If they do answer but don't ask you a question back, bless and release. If they answer and ask you a question back but their answer is like negative monster trucks. Like, Eeyore or like condoms or like stupid, you know, like bless and release. So you're looking for like the vibe in the answer. I also, in terms of like getting into the conversation, I really want people to ask, what are you hoping to find in your dating life before a first date? Like, third question. So tell me what, what are you hoping to find in your dating life? Whether you're looking for another lover or you're looking for a meaningful relationship with the right person. Say it. The right person is also looking for that thing.
Erin: Right.
Lily: Another question. So growth mindset, asking something like what's your favorite thing about yourself? Or what have you been learning about yourself in therapy in the last couple years?
Erin: Like do you reflect on yourself at all.
Lily: Yes. What's the best advice you've received lately? Who's inspiring you most? I also love the question what's made you laugh hardest lately? That's a great qualifier, disqualifier. But these like inflection points of I'm gonna want what I want. I'm going to ask the question to gauge whether or not they have what I want. After getting this information, I will bless and release or I will co create a date with them. That's how you settle proof your love life with this like structure for yourself of centering your own wants and needs and assuming that the right person that you're uniquely qualified for the right person.
Erin: Yeah. So how many at bats do you need with this? And also like, are we talking dating apps or are we talking IRL?
Lily: Like, I have a strategy for both. I think that dating apps are not the answer to finding love. They're just a silly little tool. And I think that there's a way to use them with unbothered energy when you have an IRL dating life that is joyful.
Erin: Can you dig into that a little?
Lily: Yeah. What do you want to know?
Erin: Well, I mean, dating apps are fascinating. I think a lot of women I'VE talked to hate them and find them like so frustrating. I find them to be really cool. Cool because people are out there looking. At least, you know, people are out there looking.
Lily: Right.
Erin: And they're giving you a lot of data about themselves. Like the zero effort guys. Those guys are. There's infinite zero effort guys where it's just a profile picture. It's like, and you like me. Okay. That means you saw my picture and something happened in your body. Like, get it? No thanks.
Yeah, like no effort. No thanks. 100 and you know, I don't need people to have great game on a dating app. I just need people to be, to feel open and I can tell really quickly, you know, whether I vibe somebody or not because I've now been doing it pretty intensely for a couple of years and I do like the dopamine hit of oh, so many people like me. Oh, so many people think I'm pretty. You know, like I sure do love the little self esteem boost.
And also it's fascinating. So we have like literally couldn't have less in common, that's fascinating. But I do think if you're in the right app and in the right headspace, it can be really cool. And also if you don't take it too heavy, if you treat it like.
Lily: Yes.
Erin: You treat it light and you treat it playful and you treat it like, hey, what's you know, like it. I don't bring the full weight of my hopes and dreams to every conversation. I just open the door in a fun way and see what happens.
Lily: I think that's wonderful. I think that where most people get stuck is they look to a dating app to prove that what they want is or is not possible. Because what you're saying that's it's a very readily available source of data.
Erin: Yeah.
Lily: That IRL dating doesn't necessarily provide. It's sort of like the difference between doing a stand up set to a camera versus doing a stand up set to a warm crowd. You want the, you want the warm crowd because you get that immediate feedback and you get that validation and la la la la la. Whereas the camera, it's just like, wait, is this working? I think that's the feeling of IRL dating is sort of like, am I getting, is this on? You know, so I think that a match or a message doesn't mean anything about you. But the dating app wants you to think it does. Right? The dating app, there was a study that showed that dating apps really trick the pleasure center of our brain to crave cheaper and cheaper rewards in an effort to show progress in your dating app journey.
It's like, oh, a match means a good thing. A message means a good thing. Keep going. Keep going. Because they're publicly traded companies and they want you on their platform as much as possible.
Erin: That's right.
Lily: So they make more money for their shareholders. It's similar to McDonald's fries. They're delicious, but they have sugar, they have dextrose on them that keeps you craving more, but you're never really going to be full.
Erin: Yeah. I mean, I think this is the peril of the moment we live in in every possible way that, like, all of these products, from the food we eat to the way we relate, are designed by corporations for, you know, cheap engagement. Cheap, repetitive engagement that actually leaves us feeling unnourished. Unloved, empty. Lonely. And we are not pursuing an alternative to that is harder.
Lily: It's harder. It takes more time, potentially. And we can get into the IRL strategy of it all, because I love talking about that. I also want to say I think it's a mindset and tactical strategy issue dating apps. Tactical strategy to game the system of the dating app, which will suck you of your soul and energy and time.
Erin: If you allow it, yeah.
Lily: If you allow it, right. 20 minutes a day. Set a timer. After the timer is off, set a boundary and celebrate yourself putting the phone down. 20 minutes a day for everything. Matching, messaging, whatever. If you're talking to somebody over text, obviously I don't mean that, but like, 20 minutes a day. Dating app maximum. Listen to your body if your cutoff point is lower than 20 minutes.
If it's 10 minutes, listen to your body. Give yourself that permission. No notifications, because that's going to suck you. It rob you of your time and energy. And I would also say cozy swiping. So most people are swiping on the elevator or on the subway or when they're just mindlessly sitting at their desk or whatever. Just like, okay, let me hopefully get a little shot of dopamine.
Erin: Yeah.
Lily: Cozy swiping is I'm going to intentionally carve out these 10 to 20 minutes sitting on my couch with a blanket on my lap in a moment in my day that I feel awake and better about myself than not and do it then. And if you don't feel good on a given day, don't look to a dating app to make you feel better because it's always going to disappoint you unless you sit in the driver's seat.
Erin: I love how tuned in that is because I find, like, I'll leave guys in my, like, they like me list, but I haven't necessarily liked them for a long time. Like, I'll often go through and just delete, delete, delete, delete. But then there'll be something about someone that I'll be like, I'm gonna keep you here for a minute. Sometimes it's just because they have hot pictures and then other times it's like, huh, let me see how I this isn't a no. Let me see how I feel about this tomorrow. Let me see what information I get from this profile, from this. Like, I sit with it and I usually end up deleting them.
And then sometimes I'm in a weak moment and I want attention, and I say yes, and then I have to do a whole conversation that I know is wrong. Why'd I do that? I think sometimes I just ghost because, you know, like, I try to have integrity around everything, but sometimes if things are just, like, stalled or there doesn't seem to be interest, I'm like, get away. I don't want this.
Lily: Yeah. I think that the, the fizzling is fine. I also, if you have been in a conversation for a couple days consistently, and you're just, you aren't feeling it for whatever reason and it's been consistent or you exchange numbers or what have you. Just sending a quick, like, hey, not feeling a romantic connection. Wish you the best, period. Block, delete, whatever.
Erin: I do that.
Lily: Yeah, yeah. But, but a fizzle is also fine because you don't owe someone, especially if there's been no back and forth. Owe someone anything, you know, and also I recommend, you know, decision fatigue is very real. Cognitive overload is very real. And cognitive overload is when you have too many choices, your higher functioning shuts down. You get in the, like, sort of numb space. Whenever you're in that space, I recommend, like, noticing it and turning the dating app off. Because nothing good can come from numb swiping or messaging, I think.
Erin: No, especially if you're looking for something good.
Lily: Yes. And then also I recommend getting decisive, like, knowing yourself and having the mantra of like, I get to want what I want. I get to want what I want. I get to want what I want. And then when your nervous system is freaked out by a dating app and you're afraid that nothing is ever going to happen and what you want is impossible. Get yourself to SOFT, Self Compassion, Owning your needs, Feeling your feelings, Thoughts, not facts. Like doing it on paper for 10 minutes can be really helpful. Do you want to talk about IRL dating?
Erin: Yes, I want to talk about IRL dating, because I don't even know what that is anymore.
Lily: Yeah, nobody does.
Erin: No, I would love so much for someone to ask me out IRL or for me to. I mean, like, I saw this cute guy walking his dog today, and I was like, get my dog.
Lily: Yeah, send him after him.
Erin: Yeah. I mean, just like, hopefully we'll bump into each other on the sidewalk another time, you know, because I was like, oh, this is like, you know.
Lily: Thank You More Please.
Erin: Thank You More Please.
Lily: Yeah, okay. Here's how to become a magnet for the right dates IRL. Three things, and it's a whole chapter in my book. I love this chapter more than any other chapter. I say that about all the chapters, but IRL dating, three steps. Number one is joy building. So this is the idea that joy is connective. When you leave your house to do things that bring you joy with other human beings, you are not only expanding your social circle, which is essentially the function of a dating app.
You're making new friends at that joy building thing. I don't care if it's a pottery class and nobody that you're attracted to is at that pottery class. I don't care if it's bringing you joy. It's doing its job. Because you could be invited to your pottery classmate's birthday party in three months, and her cousin's sister's brother is there, and suddenly, oh, my God, we've expanded the social circle and we've met new people, and there's IRL dating. That's how I met my husband Chris. It's like I met a friend in an improv class, and then 10 years later, her friends introduced me to their friends who introduced their friends. And Chris was in front of me.
And so joy building is really connective and good for your soul. Joy building is number one. Make a list of five things that you want to do outside of your house this month that would bring you joy and that are with other people and go and do those things and make new friends and tell your friends that you're single and you're excited to meet the right partner. Whoever, whatever. Good, tell them when you get into it.
This gets into the next strategy: co-conspirators. So this is when you choose one or a few intentional friends to sit down just like they asked you to be in their wedding. You're going to sit down and ask them for support. You're going to say, hey, will you be my co conspirator? This could mean debriefing with me after dates. This could mean being my wing woman at a bar or a restaurant this weekend. This could mean when you were at your work conference. You are eagle eyed for me, you are. I had two clients who became each other's co conspirators. They lived in different cities. They were like, we don't know how this is going to work, but we're going to figure it out. They were talking about their preferences.
They were sharing their qualifying disqualifying questions. One lived in California, one lived in the South. The one from the south went to California and was in the airport, met this adorable man, started chatting him up. Turns out he lives in California. Same city as, as her co conspirator. Huh. Interesting. Started asking, like, what are you, Are you dating? Like, what are you hoping to find? What brings you joy lately? Ends up being a great guy, Set them up because she was right place, right time, asking the right questions, they started dating.
The magic of co-conspirators is that you don't know how it might happen. You just want people to be looking out and aware of what you want and how to qualify. Disqualify so they can be a matchmaker for you. The big issue to look out for is friends who say problematic about your dating life who encourage you to settle. Oh, are you sure you're not giving them enough of a chance? Are you sure that you're, you're not being too picky? And in the book I've outlined like the five oh no no's that people could say and exactly what boundary to set.
Hey, I'm not looking for you to tell me what I'm doing wrong. I want to come up with creative solutions together because I actually know what I want. Like, that's co- conspiratorship is that honest friendship and somebody from the pottery class, from the joy building thing can become a co conspirator. Third and final step of building an IRL dating life is eye contact and saying hello. The guy on your sidewalk.
Erin: Yeah.
Lily: Hey, how's it going? Oh my God, your dog's so cute. Starting a conversation, being willing to shoot your shot.
Erin: Here's a great place to practice that. Trader Joe's. They have a billboard that says we're so nice, you might think we're flirting with you. And I'm like, aren't you? Because you are. Because I am. Because that is so fun. They're available. They're told to be present. Like, whoever is coaching those people is doing a killer job at customer service. Whoever is hiring them, too, is doing a killer job at hiring cutie pies. But I love it as a place to practice flirting, to practice connection. I know that the transaction has a time frame. You get out of it really clean. Like, love it so much because I don't think I ever, ever flirted in my life until I got separated.
Lily: Wow.
Erin: And now it is such a big part of my life, and I get to model it for my kids. They watch me, like, flirting all over the place and, and how lightweight it is and how easy it is and how nice it is to connect with people. Like, you know, I, I feel like I'm just trying to model. Like, put your shine out into the world and it'll bring back what you need. Yeah. It's a good. Anyway, Trader Joe's is my, is my tip.
Lily: Thank You More Please. Hot tip. I think that also, people are mystified by the idea of flirting. In my program, main character, I created a flirting flowchart to really spell it out for people. And if you want to learn about that program, go to datebrazen.com, basically. And I can share it right now.
Erin: Everything in the show notes, Lily, because I think people, people should share this podcast with their friends and the people they love in their lives, who they know are looking for, for love and relationships, who maybe are feeling like, no, it doesn't exist. No, it's not possible. You give me hope, Lily. Like, your approach gives me hope. Your story gives me hope. And, you know, I think a lot of us have gunk that's in the way. And your work can help us get through that gunk to the other side, what we really want, you know?
Lily: Thank you. I love what I get to do. I feel truly honored to do it. And I feel like what we're doing is different than anything else out there because it's about really centering yourself as the answer to what you want and figuring out tactically what to do, mindset wise, what to do to become the most powerful, magnetic version of yourself who believes their own desires. Who doesn't gaslight themselves into saying, no, I don't, I don't really want that. I don't really know. I don't when you do, it's okay, give yourself.
Erin: It's not possible.
Lily: Right. Don't gaslight yourself. You get to want what you want and you get to figure out how to find it. There are so many different ways to get what you want in this life. How could it be that you know all the answers right now? Really there's more life to live. So I do think that, you know, IRL dating is a practice. It's not a one and done.
It is the practice of putting yourself out there, of, of getting rejected, of then feeling those feelings and maybe doing a self compassion practice around that, building that resiliency, decreasing cortisol around trying to do these things. And then, you know, the flirting flowchart of it all is flirting is just joyful connected conversation.
Erin: Yeah.
Lily: That's all it is. And the way that you flirt is just saying hello and asking a genuine question or someone else saying hello and asking a genuine question. If their body language turns towards you, if they keep the conversation going, if you co create the conversation with them, that is flirting.
Erin: Yeah. And then that complicated lady, it's not.
Lily: And then like after 10 to 30 minutes of maybe even 5 minutes depending on the conversation and the level of body language pointed toward each other, follow up questions, some, maybe some laughter, some good like I call it a tingle. Like a good like PT vibes potentially asking, are you single? It's after 10 to 30 minutes, are you single? If their answer is no, I'm not single. Cool. Bye. Thanks.
So not a big deal if they are single, they say yeah, I'm single. Oh, would you, you know, maybe you want to go for a coffee sometime? Like oh, oh no, I, I'm good. I'm not dating right now.
Erin: Oof.
Lily: Ouch. But yeah, it's fine. Doesn't mean anything about you. And there are people who will be like, oh my God, they just asked me out. Oh my God, thank you so much. And then they'll co create a date. I don't care who asks who out first. I care if they pick if the person. Both people are picking up the ball and saying yes. What about this date? The other person's yes. What about this restaurant? Yes. That sounds great. Yes, I'll make the reservation. That back and forth is what you're looking for.
Erin: Yeah, I love this conversation so much. I want to ask you if there's any piece of wisdom you want to share with my audience of women over 40 who are looking to live their best possible lives. The most satisfied, joyful, pleasure, filled lives. In the second half, what is it that you would leave them with? Well, other than buy your book, which we'll put in the show.
Lily: Thank You More Please is a great read. I think that you can't say the wrong thing to the right person is, you know, something that I say all the time. It's true, you cannot say the wrong thing to the right person. You haven't messed up the right thing for you.There's more life to live. You haven't messed up the right thing for you.
Erin: You can't say the wrong thing to the right person. Oh, no, I said it wrong or I texted at the wrong time or I did whatever. Like, nope. If it's gonna happen for you with this person, it's gonna happen for you with this person.
Lily: Yeah, you can't say the wrong thing to the right person. The right person is also looking for you. And the last, last thing that I'd leave you with is if that you don't. If you don't believe me that it is possible. People listening, that's okay. Believing perfectly 100% of the time is not required to getting what you want. I think that becomes so stressful. Oh, I'm having negative thoughts and it's not going to happen because I'm manifesting negative things.
Erin: Losing hope, right? Yeah.
Lily: That's just a human condition. There are ways to solve for that. But if you don't believe it, just borrow my belief. I'm here in Brooklyn believing it for you that it is possible until you can believe it for yourself.
Erin: Lily, thank you so much for coming on.
Lily: So glad to be here. It was so fun.
Erin: Thanks for listening to Hotter Than Ever. I hope you enjoyed this conversation with Lily Womble about dating and relationships and looking for love. I know I did and I can use all the smart advice I can get in this arena. How about you? Is there someone in your life who is out there dating on the apps or out in the wild and needs to hear this conversation? Share this episode with them. It is so easy to just share it from inside whatever podcast app you're listening to. Do that and I guarantee they will thank you for it.
Hotter Than Ever is produced by Erica Gerard and Podkit Productions. Our associate producer is Melody Carey Music is by Chris Keating with vocals by Issa Fernandez.
Okay, I'm gonna go flirt with some guys on the apps and hopefully set up a date or two. IRL for this coming weekend. I will let you know how it goes. In the meantime, I'm just gonna keep flirting with the checkout guys at Trader Joe's because it's excellent practice and they really are adorable.
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