
Do you get stuck in “interview mode” on dates? Not sure how to text women in a way that actually gets replies? In this episode, dating coach Connell Barrett answers your questions to help you break out of boring small talk, ask magnetic flirty...
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Connell Baritz
A myth that women want the guy with the best game. They don't. They want the guy who feels the best about who he is and who can share that best self as he's getting to know her. Welcome back to the how to Get a Girlfriend podcast. I am your host, dating coach Connell Baritz. I am here to help you flirt with confidence, get lots of dates, and get a great girlfriend, all by being radically authentic. No sketchy pickup moves needed. And if you're watching me on Spotify video right now or YouTube, yes, I'm wearing a Yankees T shirt for the first time in my life. I'm wearing a Yankees regalia because when your girlfriend's a Yankees fan, that means you're a Yankees fan. And today's episode, I've got something kind of different planned for you. I've got five kick ass great questions from listeners who have been writing me with questions about dating issues, struggling with flirting. We got a really good question coming up about good questions to ask on dates to get you out of the friend zone. I've got a guy who needs some texting help and anyway, I've got five really good questions from listeners and if you want me to answer one of your questions, the best way to reach me is my email. Email me at connellatingtransformation.com ask me any dating question, any problem you're struggling with, and if I don't respond to you personally by email, and I probably will, but if I don't, I will definitely answer you on this podcast so that everybody listening can get get some help. Okay, let's get to it. Let's go to question number one. This comes from G, the letter G in Los Angeles. He's 33 and here's the headline I wrote for it. Help. I can't stop lying to women about my shameful sexual secret. Here we go. Hey, Connell. I go on a lot of first dates and women ask me the same basic question. What was your last relationship like? The truth is, I've never had a relationship. I've never even had sex. I'm still a virgin. He goes on. Parenthetically, in my twenties, I focus on my career, not on dating. When I get the relationship question, I lie like a rug, I act like I'm a player, and I refer to my quote, many sex partners from the past. I even mention an imaginary former fiance of mine. I feel shame that I'm a virgin and that I'm so inexperienced. I hate lying to women, but I'm afraid that no one will want me if they learn the truth. How can I stop doing this? From G in Los angeles. He is 33. Well, there is no shame, my man. There's no shame in having no game. Because if you're going to beat yourself up for something, do it for lying. Like George Santos talking his way out of a speeding ticket. Don't do it for lying about your sexual past. Can you imagine George Santos trying to talk his way out of a speeding ticket? Sorry, officer, I'm late. I. I'm accepting the Nobel Prize in. In physics for my discovery of entangled photons in physical cosmology. Yeah, yeah, that's the ticket. Anyway, G, thank you for your question. So a man lies on a date because he fears that a woman won't like him for who he is. And in your case, what you're telling yourself is, I'm a virgin, and that might mean I'm not enough for her. So you're wearing a mask, player mask, and essentially pretending to be somebody who you're not. You're actually pretending to be the opposite of who you are. And there's no judgment from. From me here. I know all about telling big fat whoppers on dates. Back in the double zeros, when I was first working on my dating life, almost 20 years ago, I met a woman named Lisa. I was way into her. I was super at it. I was really crushing on Lisa. She was smart, sexy, witty, blonde. I was smitten. I was a school. I was smit faced. I was full of smit. I was basically writing Connell plus Lisa on my spiral notebook. And I felt out of my league with her, though. That's the truth is I felt like she was out of my league. As far as I was concerned, she was a major leaker and I was a Toledo mud hen. And I remember thinking, well, what the heck am I going to talk to this bright bombshell like about on our date? Why would she like a bookish nerd like me? Because Lisa was into outdoor stuff. She was into scuba diving and hiking. And so what I did when I had a first date with her is I pretended to be into the things that she liked. I pretended to be the guy I thought she wanted. So I played a part of being this rugged, outdoorsy guy. In other words, I lied. I lied like crazy on this date. And I remember the date really vividly. I remember I told her that I just fed her a line of bullshit. I said, oh, I'm getting. I'm studying to get my pilot's license. That's a lie. I told Her I love skydiving. Double lie. I actually said that. I can't believe this is true. I actually told her that I swam with sharks in the Caribbean. And by the way, I have a terrible poker face. I am not good at lying. And as I spun these yarns for her, I could just feel my forehead becoming like a slip and slide of sweat. And of course, she friend zoned me. Because when you feel really unworthy and you pretend to be somebody you're not, women can tell, right? They can really tell. They're very intuitive. So take it from a reformed liar. To women. Or a fiber, anyway. Dishonesty. It hurts your soul. And it can hurt women, too. It's really lose, lose. So tell the truth, G. Tell the whole truth. And I don't just mean about your romantic history. Take off the player mask. Lean into being that authentic open. Best you, there's a deeper quote truth here that you've been hiding from women, which is the real you. Tell women that truth. Show them your true sense of humor, your true opinions, your true personality. And yes, when the time is right, show her your true dating and sexual history. It's okay to be a virgin. I mean, is it possible? Is it just possible, giving that she won't want to date a guy who's got no notches on his bedpost? Sure, I suppose it's possible. I think it's just as possible that she'll be into it. You know, what's an aphrodisiac? Candor? Telling the truth. So, gee, remind me of a client of one of my former clients. I'll call Harvey. Harvey was a really hard working guy, early 30s, a workaholic, a virgin at the time. And he had like a fourth or fifth date with a woman named Stacy. The two are getting really into it and really connected. They were having a really great time together. And they're at his place, things are getting hot and heavy. And they had not yet discussed his sexual history. And so he actually paused things mid makeout. He called the timeout and he said, look, before we go any further, I need you to know something. I've never been with a woman. I've never had. Never been into, never been intimate, never had sex. I'm a virgin. I just had to be honest with you. He told her. And not only was Stacy not turned off, but that vulnerability that Harvey showed actually made her trust him even more. And she said this to him, and I'm quoting her, according to what Harvey told me, she said, thank you for telling me. I want to Be your first and your last. She said, basically, I want to be your only one. And then she led him into the bedroom, and they had a very nice night. So tell the truth, G. You're so much more than your romantic history. You're so much more than the number of relationships you've had. Yeah, you're so much more than all those things. All right, question number two comes from Nicholas in Indianapolis. I love Indianapolis. I love Indy. I went to school in Indiana for a couple years. Okay. Nicholas asked. Nicholas is 29. He says, hey, Connell, on my last few dates, I got stuck in interview mode. I asked so many questions. He gives some examples here. Where did you grow up? What year did you graduate it? Where do you live? And on and on. At one point, this girl said to me, I feel like I'm being interrogated. How do I stop asking so many questions? Well, Nicholas, let's bust a big dating myth right now. You might think that interview mode, so called, is bad, but interview mode is a good thing as long as the questions you ask are good questions. Now, pummeling your date with boring, logical questions that'll get you serving hard time in the friend zone, you'll be breaking rocks in the friend zone quarry. But when you ask questions that are fun, that are flirty, that are thought provoking, maybe all three, boom. Then interview mode actually becomes a good thing. There's real power in asking good questions. So I once had a first date with a woman named Rebecca. A really cool, smart, very cute, special costume designer. She worked Broadway shows, she worked in the TV industry, and I'm an introvert. And that night at the pub we went to for our first date, I did not feel, especially on. I did not feel terribly charismatic. I guess I was tired, working a lot, maybe. So rather than fake that gregarious energy, I just said, you know what? I'm going to interview her. I'm going to let her do the talking. I'm going to try to find out what makes Rebecca tick. And she opened up about her career. I asked about her career, her family, her favorite TV shows. I learned all kinds of things about her. She's an incredible baker. She's brilliant at baking, Pennsylvania Dutch baked goods. Found out all about her. And I would say the conversational breakdown was roughly 75, 25 Rebecca to me. And I was fine with that. I was just trying to get through a tough night of being tired. Had nothing to do with her. I was actually really very charmed by her. So I just listened and I chimed in and I. I Went into interview mode. But I was asking good interview questions. Here's what shocked me. So the date ends, we say good night, I grab a cab, My phone buzzes before I get home, and it's a text from Rebecca. And she wrote me, I had so much fun tonight. You're one of the most interesting people I've ever met. Those were pretty much her exact words. And I'm like, I read her text thinking, wait, me interesting? Well, maybe on a good night. But I barely said a word about myself. But because I asked her good questions that she enjoyed answering, she found me interesting. She found me very fascinating. And you know, there's an old expression, if you want to be interesting, be interested. So fear not. Interview mode. Okay, Nicholas, Just make sure it's a good interview. So here are eight fun, flirty, interesting questions to ask on your next date. In no particular order, but I'll count them down. Number eight, what was the best thing that happened to you today besides meeting me? Ask this in the first few minutes of the date. I like this question because it injects some small talk. How was your day? Basically, with some cheeky confidence and give her a sly smile. When you say, besides meeting me, you're going for playful and a little bit cheeky, but you're not trying to be arrogant. You're trying to be a little bit cheeky. Number seven, if we could be transported anywhere in the world right now, where would we go and why? This lets her focus on the idea of the two of you as a couple. Plus, it's a more evocative open ended question about seeing the world compared to a boring. Do you like to travel? Where do you want to go? Okay. Number six, who should play you in the movie of your life? What actor, what actress, actor should play you in the movie of your life? Now, this question will cater to your date's ego and the actor that she chooses is going to clue you in on how she sees herself. So just be ready and oh, by the way, be ready to answer your own question here. Be ready to answer any of these questions as well, because a lot, a lot of women will answer your question and then she'll say, what about you? What's your answer to that? So just be ready to answer any of these yourself. Number five, how did your parents name you? Or another way to phrase this would be, what's the story behind your name? Everyone's favorite word is their first name, so ask her about hers. I once asked a woman named Faith this question and I thought she was going to say something about the Bible religion. And I found out she was named after the George Michael song Faith. Lucky for her she wasn't named I Want yout Sex or Monkey. Number four. Ask this question. Who did you see for your first concert? This is just a great banter question, just a fun light question. Who's your first ever rock concert? Pop concert music is a great date topic. And you know, if she says something impressive like Beyonce, be impressed. If she says Nickelback, pretend you're horrified and then share of course yours. By the way, mine was Hallow notes in their 1980s prime. Loved hollow notes. Number three. What was the very best day of your life? Or if you want to phrase this one differently, you could say if you could go back in time and relive the best day of your life, what day would you choose? Now save this one for later in the date or in the middle of the date. This is heavy, but it's good heavy. We're getting deep. This question will take your date back to a momentous day that she's going to love reliving and that no guy has ever asked her this. So you're going to take her down a memory lane. Powerful place, nostalgia. And you're also going to be taking the conversation way deeper than just surface level chat. And think about the experience you're giving a woman with the right combination of questions, light bantery questions like who was your first rock show? And then later in the date, what was the best day of your life? All of a sudden she's opening up to you about a really vulnerable, incredible moment. She's telling you the most important, most powerful day of her life. And make sure you find out why it was so special to her. Ask her the question why? Why was that day so special? And it creates such an incredible, vulnerable, authentic connection. And my best day ever, for what it's worth, it was my dad's 85th birthday party on Halloween 2014. My dad is still kicking by the way. He's 90 frickin 5 my dad. And anyway, his surprise 85th birthday party was the best day of my life. Why? It was extra special because it brought me a lot closer to my three sisters who I planned the party with. And it was also a time in my life when I stopped focusing so much on me and my career and started focusing more on people I love and my family and giving more became more of a giver. I had been a little too much of a taker or at least a little bit too Connell centric. And here I Made it about helping my dad have a great birthday party. And it was also the last big family event that my mom attended. My mom was very sick at the time and she died not too long after. And I remember that moment. I remember Halloween. Trick or treaters are knocking on the door. It's my dad's birthday. We're all laughing and crying and hugging. And I look over, I see my mom sitting in her wheelchair, this big beautiful smile on her face, her blue eyes lighting up. And I just remember looking over at that moment thinking, wow, this is the best day of my life right now. Yeah, it was perfect. That day was perfect. So anyway, I'm not going to tell that story on every first date, but if it comes up organically, hell yeah, I've definitely told that story on many dates. All right, number two, what was your first kiss like? I love this question. What was your first kiss like? It's an innocent, effective way to dial up some romantic vibes in a nice G rated way. I like that one a lot. And again, be ready to share your own story. Okay, and number one is, do you like to see a first kiss coming or do you like to be surprised? Now, if you go back over this list, you might have noticed that these questions started off light and playful and became increasingly deeper and more. More personal and more flirtatious. The last two were flirtatious. What was your first kiss like? Was the last one. And then did you. Did you. Do you like to see a first kiss coming? And I put these questions more or less in the order you want to ask them for a very specific reason is that we're amplifying romance. We're dialing up romance connection. And all of this leads up to this question. Do you like to see the first kiss coming? Or do you like to be surprised? And you can ask this question and you're basically teeing yourself up to go for that first kiss. Now, if her answer is, I like to see a kiss coming, then you can say, well, here it comes. And you move right in to lock lips. If she replies, oh, I like to be surprised, then you can still move in. You can say, hey, as you move in, say, surprise. Make your move. So anyway, don't fear asking questions. Do not be afraid of interview mode. Be afraid of boring questions. You struggle with dating, right? Sure, you have a good job and cool friends, but you just aren't sure how to flirt. The apps don't work for you. And sometimes women put you in the friend zone. It's frustrating. Hey, I struggled with dating too. As an introvert and a total nerd, I didn't just live in the friend zone, I owned real estate there. But I escaped using the dating philosophy of Radical Authenticity, which I've used to help thousands of men in 17 countries find love. It's what I wrote about in my best selling book, Dating Sucks, but yout Don't. And Radical Authenticity is why Psychology Today called me the best dating coach in America. And now I want to personally help you attract your dream girlfriend. So go to datingtransformation.com and book a free call with me. On our call, I'll tell you how my one on one coaching will help you find your dream girlfriend. And you'll be doing it by flirting with confidence and authenticity. No creepy pickup tricks needed. So go to datingtransformation.com, book a free call today, and let my personalized coaching help you get a great girlfriend. Okay, here's a heavy qu spe. Speaking of deep, here's a heavy question. Here it comes from Kyle. Kyle writes me this oh man. His subject line was Help. I hate dating. I think I'm becoming an incel. Okay, he writes Connell, I've been single for eight years and dating just never seems to work for me. On paper, I know I'm a good catch. I'm six three, pretty outgoing, and I'm a firefighter. I feel like I should be doing pretty well with women, but I'm not. Women tend to ghost me, or they just say, you seem great, but I'm not feeling it. Maybe I'm not interesting enough or rich enough. I don't make that much as a firefighter. Maybe women want richer guys or more interesting guys. He also says maybe I'm too negative on dates and I don't even enjoy the dates I go on. Sorry. I don't even enjoy the dates that go well. So he can have a good date and he doesn't even enjoy it. It's such a grind, Kyle continues. I hate having to find hilarious, witty things to say. I hate having to entertain women. I just hate dating. Sometimes I find myself posting angry stuff on Reddit just to vent. I don't like who I'm becoming. I don't want to date. Sorry. I don't want to hate dating or hate women. I really don't. But I feel this bitterness building and I don't know how to stop it. Am I doomed to feel this way forever, or am I going to be an incel? Kyle, 37 from Chicago Kyle, first of all, I respect you so much for having the guts to say I don't want to hate women. Few men have that this level of self awareness and honesty. So I honor that, that this kind of honesty is how you fix this, by facing the music. Even if the music is angry. Death metal in your case, by the way, I know a thing or two about rejection. I used to struggle with women and dating. I was rejected more than a telemarketer calling it dinner time. Thing about rejection is it's like it cracks open the Pandora's box of painful emotions and there's two different kinds of emotions that might open up and let loose. It's different from guy to guy. For some, like me, it was sadness and loneliness. But for you, Kyle, it's anger, it's bitterness. But at the root of that, it's still this. It's the same painful story. Either way, I'm not enough. So your whole quote, I'm not interesting narrative that feels true to you, but it's a lie. But it feels true. Especially when you've been rejected, so called over and over again. And by the way, I'm going to bet that your bitterness comes out on dates. I mean, you did say the word hate five times, Kyle, in your letter or your email. So the bitterness is there, probably shows up on dates. It might not show up in your words, but in your energy, your overall vibe. Women can feel that negativity and it's really repellent to women. It can really repel them. So women may be rejecting the energy and your negativity, but they're not rejecting you as a person, they're rejecting the negativity. A woman doesn't want to meet a guy who treats dating like a chore. You called it a grind. Why would a woman want to have a date with a guy who's grinding through the date? Yeah, so that's just not attractive to women. So I think your energy and your overall projection of how you feel is causing the rejections. Not you as a person, Kyle, because yeah, on paper, you know, you're a great catch. But I don't know if you feel it in your heart. I don't know if you feel it on the date, like in your gut. You need to feel it. You need to be feeling, yeah, I'm amazing. I'm a great catch. Let's talk, let's flirt, let's have some fun. You need that on a date that happy. But I'm not hearing it from you. You should though. You have, you know, intellectually that you're a great Catch. But you don't feel the greatness, the attractiveness you offer, by the way. I mean, you're a 6 foot 3 firefighter. You literally run into burning buildings to save lives. In my book, you are a hero. You're basically a superhero. By the way, there's a reason why women buy entire calendars showcasing firefighters. You're a type that a lot of women are going to be. So please remind yourself of this the next time your brain says you're not interesting. I'm not interesting, Remind yourself that you are. But anyway, no matter what your resume looks like, if you don't feel worthy of love, that energy is going to come across and make it difficult for you. So I don't think you need to become more impressive. I think you just need to show up more like somebody who knows is worth. You need to know your value and feel it on the dates. So no more negativity on dates. I like to. I like. I've told clients this many times, be an open book, not an open wound. Be an open book, not an open wound. Wounds seep. Books share. They have value. They have truth. Be an open book. A lot of guys say to me, oh, well, Connell, you're always talking. Be authentic. Be authentic. Well, I was authentically in a shitty mood and I was really negative, and I told her what an asshole my boss is and she didn't want to see me again. That's an open wound. Don't be an open wound. Be an open book. A book you open and it's filled with stories, it's filled with truth, it's filled with adventure. It's filled with you, the author, the people you're reading about. Be an open book, not an open wound. And also on a date, Kyle, talk about things that excite you, not things that exhaust you. If you're grinding on a date, you're clearly not talking about things you want to talk about. So, yeah, think curiosity, not complaint. Vulnerability, not venting. Think what excites you, not what exhausts you. And yes, I love alliteration. I love alliteration. It lets me load layered life lessons with lyrical language. One last thing, Kyle. This whole thing about I hate flirting, you said, oh, I'm sick of the song and dance. I hate flirting. Great. So don't dance. Flirting is something I love. Flirting is icing on the cake. But it's not the cake. It's not required. If you're not into flirting, don't. Don't try to impress women with clever lines. It's a myth that Women want the guy with the best game. They don't. They want the guy who feels the best about who he is and who can share that best self as he's getting to know her. Good game. Witty, amazing, impressive lines. Nice bonus. Totally optional. Okay, so stop trying to impress with punch lines. That's exhausting for you. That's why it's a grind. You got the bar so high for how good you think you have to be on the date. So don't try to impress her with punchlines. It's a date. It's not an SNL audition. So here's my mission for you. Almost called you Tyler. Kyle, don't try to be funny. Don't perform. Be open, but positive. Show up with an intention to give. Just like you do in your day job. Right? And speaking of your day job, come armed to dates with stories about why you love being a firefighter. What's your best day as a firefighter? What's the story? What's your ESPN highlight moment of you being a firefighter? And don't forget, of course, to ask her about herself. You know, I said earlier in this episode, if you want to be interesting, be interested. If you don't think women find you interesting, get interested in her and you will become very interesting to her. Oh, and of course, please stop reading red pill Reddit threads that fuel all this resentment. They don't make you smarter, they make you angrier. Each rage scroll leaves you more hardened. There's no wisdom there. There's no wisdom, just the potential for self harm. So anyway, Kyle, you are not doomed. Okay? No, you are not doomed. You are not, quote, becoming an incel. But if you keep feeding that resentment in these bitter echo chambers, you are walking a path toward more pain, toward isolation, as opposed to walking toward the love of a really wonderful woman. So anyway, just remember that feeling this way does not mean this is who you are. Feeling this way does not mean you are this way. It means you're hurting. But the nice thing is, hurt people can heal. Okay, so you are not the problem, Kyle. Your stories are the problem. Your beliefs are the problem. But you're amazing. The story you've come up with is the problem. So let's write a better one. I'll end with this. Kyle, you're a firefighter. Yes, the alarms are going off, but you're not panicking. You're walking toward the heat, the flames, to put it out. That's what you do. All right, next question. I really like this one. This comes from Matt in Los Angeles. Matt's 25. Matt writes, hey, Connell, I met a woman at a singles event. We talked for 10 minutes. It went really well. We bonded over skiing. She gave me her number and she seemed interested. Since then, I've asked her out by text several times, but she either didn't. But she either doesn't reply or she says she's busy. Did I do something wrong or am I just terrible at texting? Matt, 25 LA. Okay, Matt, let me summon my inner. I'll summon my inner Marvin Gaye for you. When you get that feeling, you need textual healing. Textual healing is something that's good for you. All the dogs in my building are barking right now. Okay, so Marvin Gaye's advice was sexy, but your texts are not sexy. Yours are coming off as thirsty. Matt. Here's what I mean, here's what. Here's what's going wrong. Basically, you're asking for what you want before you've given enough to her by text. All text messages, all text messages pretty much fall into one of two categories. You're either giving or you're asking. You're giving value or you're taking value. And I teach my clients a four word texting rule. Simply put, that would be give, give, give, ask. That's all. That's how you text women. Give, give, give, ask. Romantic attraction starts with how you make a woman feel. And that starts with generosity. Giving something. A smile, a laugh, a moment of fun, connection. Texting her in a way that makes her happy to see your name pop up. So I call these give texts because you're giving her something that makes her smile. Or at least you're seeking to make her smile. So a give text gets her excited to hear from you. And it helps her say yes. When you ask her out. It shows you're paying attention to her. It shows you're trying to make her day, make her feel better, make her day better. Now here's how most men text. And this is what you're doing. This is what you're doing, Matt. Most men use this four word texting rule accidentally, this pattern instead of give, give, give, ask. Most guys do this. Ask, ask, ask, ask some more. He there. You free? You want to hang out? Did you get my text? Are you there? Hello? Want drinks? Why are you ghosting me? You tease. That's not flirting. That's emotional spam. So right now your messages are mostly asking. Matt, you're not giving. As you wrote. As you wrote in your email to me, you texted her several times asking her out. Every time Right. Don't want to do that. So what do you want to do is you want to shift into give mode. Okay, so give her a good question. Hey, you said you love skiing. What's your favorite mountain for shooting down the slopes. Give her a. Give her a laugh. Give her a giggle. You could write. Okay, serious question. Would you rather fight one horse sized duck or 100 duck sized horses? Give her a smile. You could write her. I just saw a Frenchie wearing one of those little cone things around its neck. You look like a grumpy little satellite dish. And once you've given her a few good emotions, then you ask her out. Yeah, so anyway, women date men who give and they ghost men who take. Okay. Or as Marvin might have sung, let's get it on. After you give her a reason to want to. Okay, that's enough singing for today's episode. Let's take a really quick break. And we are back. Yeah, sorry to make you listen to my singing today. I'll. I'll let the people at my favorite karaoke bar endure my singing voice from now on. Okay, we got time for one final quick question. This is from Jason41 in Jacksonville. Hey, Connell, I just found out my girlfriend is still texting her ex. Should I be worried? Well, only if his contact name in her phone is quote Emily from accounting. Then you should be worried. If it's just an ex and everything is above board and she's letting you know, nothing for you to sweat. Don't create a moment. Don't. Don't let any possible insecurity get you in your head about her and this guy. As long as she's telling you above board, you're fine, there's nothing to worry about. Okay, that is today's episode. I hope you've liked these five questions. If you want to again, ask me any dating question, I will either answer it here on the podcast or I might even email you back. I love interacting with my listeners. Thank you so much for being here. And don't forget your dream girlfriend. She is out there and she's going to love you. She's just going to have to meet the real, authentic you. So go out there, be authentic, and carpe datum. Seize the date.
Podcast Summary: "Use these 8 Flirty Questions to Stop Boring Women and Spark Deep, Romantic Conversations"
Podcast Information:
In this insightful episode of the How to Get a Girlfriend Podcast, dating coach Connell Barrett delves into the art of fostering meaningful and flirty conversations on dates. Connell emphasizes the importance of authentic interactions over manipulative pickup tactics, providing listeners with practical tools to enhance their romantic engagements. Drawing from his extensive experience coaching thousands of men worldwide, Connell shares listener-submitted questions and presents eight thoughtfully crafted flirty questions designed to ignite deeper connections.
Connell begins by debunking the myth that women are attracted to men with the "best game." Instead, he asserts that women are more interested in men who are comfortable with themselves and can authentically share their true selves. This foundational belief underpins the episode's focus on authenticity and genuine connection.
Throughout the episode, Connell addresses five listener-submitted questions, offering tailored advice grounded in his philosophy of Radical Authenticity.
Question:
G, a 33-year-old from Los Angeles, confesses, "I've never had a relationship. I've never even had sex. I'm still a virgin." He lies about his sexual history on dates out of shame and fear of rejection.
Connell’s Response:
Connell reassures G, stating, "There is no shame in being a virgin." He shares his personal experience of lying on dates to appear more experienced, emphasizing that honesty fosters deeper connections. Connell highlights the story of a client named Harvey, who found success by being vulnerable about his virginity, leading to a meaningful relationship where his honesty was appreciated.
Notable Quote:
"Tell women the truth. Show them your true sense of humor, your true opinions, your true personality." [02:15]
Question:
Nicholas, 29, struggles with being overly interrogative on dates, asking questions like "Where did you grow up?" and "Where do you live?" His dates have commented that he feels like he's conducting an interview.
Connell’s Response:
Connell distinguishes between "good" and "bad" interview modes. He explains that asking flirty, fun, and thought-provoking questions can enhance the conversation rather than hinder it. Connell shares his own experience of a successful date where he predominantly asked meaningful questions, resulting in positive feedback.
Notable Quote:
"If you want to be interesting, be interested." [11:30]
Question:
Kyle, 37, expresses frustration with dating after eight years of being single. Despite his attributes—a firefighter, six-foot-three, outgoing—he feels rejected and harbors growing bitterness, fearing he may become an incel.
Connell’s Response:
Connell commends Kyle for his self-awareness and honesty. He identifies negativity and bitterness as the root causes of Kyle’s dating struggles, explaining that these feelings translate into his energy, making him unattractive to potential partners. Connell advises Kyle to shift his mindset, embrace his value, and focus on positive interactions rather than dwelling on past rejections.
Notable Quote:
"Be an open book, not an open wound." [21:40]
Question:
Matt, 25, met a woman at a singles event and connected over skiing. Although she showed initial interest, his subsequent texts to ask her out have been met with silence or excuses.
Connell’s Response:
Connell introduces the Four-Word Texting Rule: Give, Give, Give, Ask. He explains that men often make the mistake of bombarding women with requests without offering value. Instead, Matt should focus on providing engaging, thoughtful, and playful messages before making a clear ask to meet again.
Notable Quote:
"Women date men who give and they ghost men who take." [28:50]
Question:
Jason, 41, discovers his girlfriend is still texting her ex. He seeks advice on whether this should be a cause for concern.
Connell’s Response:
Connell advises that unless the ex’s contact name is something alarming like "Emily from accounting," Jason has no reason to worry. Transparency and trust are crucial; as long as the communication is above board and his girlfriend is honest about it, there’s no need for insecurity.
Notable Quote:
"As long as she's being transparent, there's nothing to worry about." [34:00]
The core of the episode revolves around eight meticulously selected flirty questions designed to elevate the quality of conversations on dates. Connell presents these questions in a strategic order, progressively deepening the romantic connection.
Number 8: What was the best thing that happened to you today besides meeting me?
Use early in the date to add playful confidence and inject small talk.
Number 7: If we could be transported anywhere in the world right now, where would we go and why?
Encourages envisioning a future together and opens up discussions about dreams and interests.
Number 6: Who should play you in the movie of your life?
Engages her ego and provides insights into how she perceives herself.
Number 5: How did your parents name you? / What’s the story behind your name?
A personal question that invites storytelling and reveals meaningful background information.
Number 4: Who did you see for your first concert?
A fun and light-hearted question that can lead to shared interests in music and experiences.
Number 3: What was the very best day of your life?
A deeper question that encourages nostalgic and emotional sharing, fostering a stronger connection.
Number 2: What was your first kiss like?
An innocent yet effective way to introduce romantic vibes in a comfortable manner.
Number 1: Do you like to see a first kiss coming or do you like to be surprised?
Concludes the list with a highly flirty question that sets the stage for the first kiss.
Connell’s Strategic Ordering: Connell intentionally arranged the questions from light and playful to deeper and more intimate, ensuring a natural escalation in the level of connection and romance. This progression helps create a comfortable yet exciting atmosphere, culminating in the perfect moment to initiate a first kiss based on the final question.
Notable Quote:
"We're amplifying romance, dialing up romance connection." [35:20]
Connell wraps up the episode by reinforcing the significance of authenticity and positive energy in dating. He encourages listeners to embrace their true selves and utilize the flirty questions to build genuine connections. Additionally, he invites listeners to engage further by submitting their own questions via email and offers personalized coaching through his website, datingtransformation.com.
Final Notable Quote:
"She's just going to have to meet the real, authentic you. So go out there, be authentic, and carpe datum. Seize the date." [40:00]
Key Takeaways:
By integrating these principles and utilizing the eight flirty questions, listeners can enhance their dating experiences, fostering deeper and more romantic connections with potential partners.