
Not knowing what to say or how to flirt on first dates can get any guy trapped in the dreaded friend zone. In this episode of “How to Get a Girlfriend,” dating coach and bestselling author Connell Barrett shares 37 flirty things to say that spark...
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The most powerful thing you can do verbally on a first date is tell a woman she's sexy and tell her why. As long as the why is a trait, a quality, not about her physical appearance or her body. Welcome back to the how to Get a Girlfriend podcast. I'm your host, dating coach, Connell Barrett. I'm an author. I am a dating coach of 14 years, and I want to help you flirt with confidence, authenticity, to know what to say, get girls giggling and women into you so we can get you a great girlfriend. And to do this with authenticity, not a bunch of sketchy, weird pickup artist moves. Women want you. The authentic you. Your mom was right. Women like you for you, or they will. And today's episode is for you. If you struggle on dates with flirting and what to say and how to say it. So many men deal with awkward pauses on dates, or they have good, logical, analytical conversations and they think the date went well. And then you get those four or five words that you hate hearing from women. I didn't feel a connection. Oh, that. That sucks. I remember a first date I had where I thought it went well. I thought I was funny. I thought we had a good, deep, fun conversation. And then she texted me, just not feeling it, Connell, but we can be friends. And I came home and I was so disappointed and frustrated. Not at her, but just at my frustration and being stuck, that I took this stapler on my desk and threw it across the room, smashed right into this giant wicker chair that my roommate had. And she was not happy. She was like, why are you throwing shit at my wicker chair? And this was way back when I struggled with dating. So today, I'm going to give you 37 things to say on first dates. 37 flirty things to say. Now, one little caveat before I run through these. 37. And I'm going to crank through these in, like, 15, 20 minutes, tops. But before I give you these 37 things, think of this list as ideas to have germinating in your mind, not things to memorize. I don't want you memorizing things on a date. I don't want you to feel like you have to go into the date with literally 37 things ready to say. You don't want to sound scripted and robotic. Women like a present authentic guy who's in the moment with her. That said, it is good to have a few things in your back pocket, so to speak. Maybe not literally. So here's what not to do for this episode. Don't do what I did. Many Years ago, I once had a first date and I was so nervous and so unsure about what to say and how to flirt that I had a printout of like 15, 20 things to say. Like this cocky line, this funny story, this, this teasing nag type thing, which was a thing at the time. And. Hi, sweetie. My cat Parmi is crawling up on my lap right now. Hold on. Hey, sweetie. Okay, I have a little orange ginger tabby cat on my lap. Hi, baby. Hi, sweetie. Okay. And on this first date, I had a 8 1/2 by 11 printout of all these funny, witty, cool things to say. And. And I would excuse myself during the date and I would say, hey, I'll be right back. And I would go into the men's room and like, look at the list. This was before iPhones, by the way. And like, oh, let me say this cool, funny line to her. So I don't want you to think of today's episode as things I want you to memorize. Just integrate them, just listen to them if you would. 37 funny, flirty things to say. And I think number 26 is especially powerful if you really want to get out of the friend zone. And most of these things you're about to hear are playful. They're all, almost all light and playful. And playfulness is really what flirting is about. Flirting is about play. And as my cat licks my right arm, I'm getting a cat bath right now while recording the podcast. Anyway, so let's get to it. Let's rock through these 37 things to say on first dates. Let's rock through. Why do I sound like a FM classic rock DJ? Let's rock through these things. Here we go. 37 flirty things to say. Number one, if this goes well tonight, we can name our first child. Hinge algorithm rolls off the tongue, right? That's something you could say early in the date. You could also text that beforehand if you like. Number two, thank you for actually looking like your photos. I've known you for three minutes and this is already the healthiest relationship I've had. That's a really good thing to have ready to say because we all know what it's like. Most of us know what it's like to be on a date and the other person just does not look like their photos. Flirty thing to say. Number three. I confess I was nervous every time somebody walked in and I kept wondering, is that her? I discover what a good thing this was to say on many first dates. Really owning your vulnerability, being honest about feeling Nervous is really disarming and a lot of women really like it. Number four, let's make a deal. If the next song is terrible, we'll go somewhere better. And if it's a banger, you tell me your most embarrassing high school story. Now, the idea behind this one is you're looking for moments on first dates to turn the interaction playful, raising the stakes, right? So you can literally grab a song that's. Or not grab it, but listen to the song that's playing. If it's a, you know, if you're at a bar where there's a lot of music playing and turn it into a fun little get to know you game. Okay. Flirty thing to say. Number five, here's a good one. Here's a classic, a Connell classic. Let's say she looks down at your shirt and your outfit, which of course will happen at some point. You could say. And you have to say this with a very fake, arrogant cheekiness to it. You say, excuse me, my eyes are up here. Please don't treat me like a piece of meat. So this is a misinterpretation, an old school pickup move that I learned back in the day that I still like. You're misinterpreting what she's doing as her looking at you like you are a sex object. Think how different that is. Most women are used to being objectified or treated like a piece of meat. So you are flipping the script there. Okay, let's go to number six. If we could teleport together anywhere in the world, where would we go? It's a good one. It's a fun, different way to ask about travel. It's a great question that allows her to imagine herself with you traveling, which now we're asserting. Her and your togetherness. Flirty thing number seven to say on a date. Who should play you in the movie of your life? Now, just by the way, for all of these, for any of these that are questions, be ready to answer the question yourself. Because a lot of women will answer. And then she'll say, what about you? Who should play you in the movie of your life? And I like this question because it gives a woman a chance to really think. That's a question she's almost certainly never been asked before. Most every other guy is saying, where'd you go to school? Where'd you grow up? You know, how many brothers and sisters do you have? There's nothing wrong with those questions, but it's nice to keep things playful. Keep it fun. And then her answer would be, really interesting. Who would play her in the movie of her life and then ask her why. Ask her why? I don't remember if I asked my girlfriend Jess that on our first date. I might have, but if I had, she might have said something like, aubrey Plaza. My girlfriend is a big Aubrey Plaza fan. Or at least has a very dry, snarky personality like Aubrey Plaza does. So who knows? So anyway, her answer to this question could really help her open up to you and have her show a side to you that you might not know about. Number eight, just so you know, I never kiss until the 16th date. I'm not easy. Number nine. What is something that you're weirdly good at? Number nine is a really good back pocket question to have ready. If there is a lull in the conversation and you're trying to avoid a long awkward pause because everybody has things they're secretly or they're weirdly good at. Everybody has something. Number 10. I'm actually pretty introverted, but you're making this feel easy. If you're introverted, which many men are, let her know that you're introverted. But she's making this date go well. That'll make her feel so good. All right, let's go to number 11. Flirty thing to say. Number 11 on first dates. So who's the weirdest guy you've ever had a date with? If you say me, I'm leaving. This is a really good way to talk about dating in a way that's not boring and too meta, too analytical. What you don't want to do. Do not talk about dating too much on first dates. So how's bumble treating you? Oh, here's my bumble experience. Here's my hinge experience. Talking about dating too much on a first date, it's too meta. It's like talking about why a joke is funny. If you overly analyze it, it stops being funny. But if you ask her about the weirdest dude she had a date with, she'll have a story. Every woman has a weird first date story about a guy, and that's actually a fun way to talk about dating for a little bit, especially in the first 10 or 15 minutes of a date when you're trying to just get comfortable in each other's company. Number 12, you're either the coolest woman I've met in a long time or the weirdest. I'm just not sure which one yet. This is a classic old school move called the push pull. You are giving her a little bit of a push, a tease she might be weird, but you're also giving her a pull. As in pulling her toward you. Figuratively. But you also might be the coolest, but I'm not sure which. I said this to my girlfriend on one of our first couple dates and she really liked it. She later told me how much she liked that. Number 13. You have this way of pausing before you answer that makes the next thing you say sound important. Important. Ooh, notice that. Say it if you want to. Number 14, who is your middle school crush? And if she likes that question, follow up with number 15. What was your first kiss like? First ever kiss. Was it adorable or was it super awkward? A good thing to talk about in the first half of a first date is bringing up the topic of. Of childhood. You know, teenage innocent loves and crushes and first kisses. Most people have either a cute story or an awkward story. Okay, number 16. Oh, by the way, my mom and dad are coming later. They're so excited to meet you. Speaks for itself as just a silly, fun, dumb thing to say. Number 17, if you could go back in time and relive the best, best day of your life, which day would you choose? That's a thinker. Now we're getting into more thoughtful questions that are a little bit deeper but still intellectually and emotionally compelling to a lot of women. It's a powerful question. Again, be ready to answer that yourself. If I could go back in time and relive the best day of my life, I would probably go back to my dad's surprise 85th birthday party. Halloween 2014. And my mom was still alive at the time. She was there. I co planned the party with my sisters and it was just an amazing day. My dad cried, my mom cried. Everybody was just so happy. It was an amazing night. My dad's birthday is Halloween. Okay, number 19. I had a feeling this was either going to be awkward or really fun. I'm relieved it's the Second one. Number 20, huge question that will determine whether or not we fall madly in love. Pineapple on pizza. Yes or no? I think I might have to give you the rose I brought tonight. It's between you and one other girl. She'll be here in a few minutes. So you're cracking a joke about how there's another woman coming to the date. You're basically making a joke about being on a group date with her. Okay, quick pause. By the way, if you would like to learn more about how my coaching works, if you want personalized one on one help to help you have better first dates and approach women and get a great girlfriend. Then go to my website, datingtransformation.com I make myself available to take on new clients from time to time, so go to datingtransformation.com if that appeals to you. If you're not looking for coaching, no worries. Here's something else you can do. I. I want to send you a free copy of my book if you would like. I wrote a a pretty successful book called Dating Sucks, but yout Don't. It's all about my best dating advice as of a few years ago when it came out. So if you'd like a free copy of my book, just email me connellatingtransformation.com Subject free book and I will email you a free book. Okay, let's go back to first date questions. Number 22. There's a fire at your house. All pets and people are safe. You can grab one item beside your phone to save. What do you go in and save? Had so many great conversations. Start with that question number 23. I have a theory that everyone has one specific opinion that they'd argue with strangers about. What's yours, number 24? I have to admit, I have a really nerdy side. What's the nerdiest thing that you're into? I'll go first if it helps. And again, be ready to go first. Have a nerdy thing that you're into. My nerdy thing is improv, comedy, musical theater. I nerd out on podcast history stuff. That's me. Don't be afraid to show your nerdy side. Okay, number 25. Let's pick a random person here and decide what their secret hobby is. That's fun. You get to look around the room and make up backstories about people. What this does is it puts you and her in collaboration. You're now doing something together which is good for a first date. And here's number 26. If you do nothing else from this, if you use no other flirty statement or line or question from this list, I Definitely recommend number 26. You know what's really sexy about you? You're so smart and funny. I'm just trying to keep up. The most powerful thing you can do verbally on a first date is tell the woman she's sexy and tell her why. As long as the why is a trait, a quality, not. Not about her physical appearance or her body. Okay. So feel free to make yours more personalized than you're smart and funny. Find something very specific you find sexy about her. But yeah, lay it out there. It's hard to get friend zoned. It's hard to get friend zoned if you look her in the eye and say, damn, this is really sexy about you. Okay, number 27, explain TikTok to me like I'm your grandfather. Go. Number 28. You're very present when you talk to people. Most people are in their heads, but you're right here in the moment with me. Number 29. I'm trying to figure out if you're actually this charming or if I'm just easily charmed. It's probably both. Number 30, your eye contact tells me that you're thinking something devious. I really like this one. It's a good little bit of a cold read, right? You can imagine that you know what she's thinking or her what her eye contact is telling you. She might be thinking something devious or use the word naughty if you are feeling extra bold. Naughty is a good flirtatious word to use. Number 31. I like that I don't have to perform or be somebody else around you. Let me. Let me say that again. I screwed it up. I like that I don't have to perform or be somebody. I'm not around you. It's a beautiful thing to tell somebody. By the way, this should go without saying, but I'll say it anyway. I want you to mean any of these things that you use. Don't just use these because dating coach Ginger Connell dude said to really mean them. What makes any quote unquote line or thing you say work? It's not the words. It's not the syntax. It's the emotion. It's the authenticity. It's the force, the truth underneath it. That's really what makes it work. Okay, number 32. Do you like a first kiss to be a surprise or do you like to see it coming? Now that's a flirtatious thing to say. Notice how this is number 32. So it's late in our 37 list. Right toward the end of a date, as you're leading to that first kiss. Oh, man. Dialing up the tension. Maybe you guys are touching a little bit, being a little bit touchy feely, sitting closer. And then you just say, do you like the first kiss to be a surprise or do you like to see it coming? You're dialing up that romantic tension. Number 33. I'm trying to figure out what your friends would tell me about you if I bribed them. That's a good one. Number 34. Here's a really good Way to ask her out. Ask her out on date number two. But you do it on date number one. Late in the date. Here it is. Grab your phone and say, hey, chat. GPT. Should I ask this cute girl out for a second date or should I leave right now for my own safety? Really charming, very playful. Number 35, I was warned about you by myself earlier today. Oh, man, I didn't listen. Or if you want to amp that up, I was warned about how charming I thought you would be today by myself earlier today, but I didn't listen. That's a good one. Number 36. After the first kiss, if you have. If you go for and get that first kiss on a first date, which I certainly recommend to try, if it was going pretty well, at least on a nighttime date after that first kiss, you say, wow, you're a really good kisser. And you pause. Almost as good as me. It's so close. It's a cheeky line that can. You give her sincerity and tenderness and heart, which women love. And then you add a little bit of cheekiness, which women tend to also love. And then number 37. This is a great way to end the date. You say, I don't like to play games, so I'm just going to say it. I like you. Let's do this again. Ask her out. Let her know you like her. Let her know you want to see her again. Yeah, that's just what works. Flirting can be complicated at times. It can be scary, it can be confusing. But it can also be as simple as, I like you. I want to see you again. All right, Those are my 37 things to say on first dates. Don't say them all. Don't memorize all 37. Just integrate this list and look for a moment on your next first date. When one, one or two of these phrases comes to you, that's how you want to use this. And again, if you are tired of hearing, oh, I didn't feel a connection, let's just be friends. Or just having women meet you for a date but not want to see you for that second date. Dude, I remember how that felt. That was a big pain point for me back in the day. Then go to datingtransformation.com you can book a free call to talk with me about how my coaching works and let's see if I can help you. Or just email me connellatingatingtransformation.com subject line free book and I'll send you my book for free. All right, until next time. Thank you so much. For listening, Sam.
How to Get a Girlfriend with Connell Barrett – Episode Summary
Episode: 37 Flirty Things to Say on First Dates to Escape the Friend Zone and Get Second Dates
Date: May 13, 2026
Host: Connell Barrett
In this episode, dating coach Connell Barrett dives into the art of flirting on first dates, promising to arm listeners with 37 flirty things to say. His aim is to help men authentically break through awkwardness, escape the dreaded friend zone, and land more second dates. With a playful, personal, and empathetic approach, Connell stresses the power of authentic, in-the-moment conversation over memorized lines, sharing both practical tips and memorable quips to help listeners connect truly and confidently.
Connell presents each phrase or question with context, suggesting how and when to use them to bring playfulness and connection into the date. Here’s a breakdown (grouped in themes, with standout examples and selected timestamps):
On complimenting authentically:
“The most powerful thing you can do verbally on a first date is tell the woman she's sexy and tell her why. As long as the why is a trait, a quality…not about her physical appearance.” [00:03 & 23:00]
On playfulness:
“Flirting is about play.” [04:20]
On being present:
“Women like a present authentic guy who's in the moment with her.” [02:00]
After sharing a possible first-date compliment:
“You're dialing up that romantic tension.” (on #32: Do you like a first kiss to be a surprise or do you like to see it coming?) [32:00]
Connell wraps by encouraging listeners to trust their authentic selves and use these lines as tools to break free from awkwardness—a guide to real connection over forced performance. He reminds listeners of his coaching and free resources, but the heart of the episode is summed up in his exhortation:
“Flirting can be complicated at times. It can be scary, it can be confusing. But it can also be as simple as, I like you. I want to see you again.” [37:35]