How to Get a Girlfriend with Connell Barrett - 47 Flirting Tips So You’ll Never Run Out of Things to Say with Women

Episode Date: April 16, 2026

If you struggle with what to say and how to flirt, help has arrived. In this episode of “How to Get a Girlfriend,” dating coach and bestselling author Connell Barrett gives you 47 simple, actionable ways to spark attraction with women, without cheesy gimmicks. Learn how to be playful, authentic, and confident, so you’ll never run out of things to say—on dates, over text, or when approaching women.WANT TO BECOME AMAZING AT FLIRTING? BOOK A FREE CONSULTATION CALL WITH CONNELL TO LEARN ABOUT HIS 1-1 COACHING: DatingTransformation.comNOT SURE HOW TO TALK TO WOMEN? GET A FREE COPY OF CONNELL’S BESTSELLING BOOK, “DATING SUCKS BUT YOU DON’T”:Email “Free Book!” to: [e-mail]

Flirting is as easy as saying these three simple words. I like you. Welcome back to the How to Get a Girlfriend Podcast. I'm your host, dating coach, and bestselling author, Connell Barrett. I'm here to help you know what to say, flirt with confidence, and attract an incredible girlfriend into your life. And do it all by being authentic. Flirting is about authentically letting women know who you are, what you want, and how you feel.

That's how we make women feel. Now, today I want to help you go from friendly and safe to fun and flirty. I'm going to give you 47 flirting strategies, 47 quick flirting tips so that you always know what to say and can start making some sparks happen on dates over text in person when you approach. Let's get to it. Let's go right into number one. Flirting tip number one is flirting is as easy as saying these three simple words. I like you. It's that simple. Flirting is not about saying perfect witty lines. It's not about playing it

cool. Flirting is actually very simple. I like you are the three most important words. Unless you're married, and then those three important words are delete that text. Don't let my wife see it. But otherwise, I like you can be as simple as that. I've been on dates in the past where I would just look a girl in the eye and say, you know what? I'm really liking you. You're fantastic. Let's go out again. And that's more than enough. So flirting is as easy as saying, I like you. Flirting tip number two. Flirting isn't playing it cool or being some fake alpha male or creating amazing content. It's not fancy lines. Flirting is one thing. Play. It's about playfulness. The Oxford English dictionary defines flirting as quote playing at love and that's all it is it's play

and there's a lot there are a lot of myths about what flirting is about how to talk to women be sure I should be sexual should I play it cool should I what do they say on Reddit convey higher value be a high status guy look sure a woman wouldn't mind dating a guy who has a high status position in society. But the bottom line is, terms of what to say and how to say it, lower the bar for how good you think it needs to be. You want to think playful.

What does that look like on a date, perhaps? It can mean a staring contest. Thumb wrestling. Playing two truths and a lie. What does that look like when you approach? You come up with a fun, playful icebreaker. I once approached a woman, this was in a Vegas lounge years ago. I was in a fun, playful mood.

And I walked up to a woman and I said, oh my God, it's you, my ex-girlfriend. How have you been? You look amazing. I had never talked to this woman before. I was playing a part. And she laughed and said, oh, my God, honey, how are you? You look amazing. And we did this fun little role play.

It all started with playfulness. So flirting is about play, in a word. play. Okay, flirting tip number three. If you run out of things to say, here's a back pocket question you can have with you to avoid awkward silences, especially on dates. Here's a good back pocket question. What's your secret talent? Asking a woman what her secret talent is. That's a great thing to have in your back pocket because secret, there's something kind of sexy or maybe sexy is not the right word enticing about the word secret. A secret is something you share with somebody who is special to you. And it's a question she's not usually asked. Most women are asked, how is your day?

What do you like to do? Where are you from? And that get to know you stuff is part of dating. That's okay. But if you are afraid of an awkward silence on a date, then come armed with that question. What's your secret talent? Flirting tip. Number four, tell her your secret talent. Have one ready because any question you ask a woman, you should be ready to answer yourself. By the way, this also works over text. It's not just about first dates. My secret talent is I can do coin magic.

I used to take magic lessons and magic classes so I can make a quarter come out of your ear in any given moment with a little bit of practice. Flirty. Flirting tip number five. before a first date, prepare three personalized questions for your date. Three things you're going to have ready to talk about so that you never run out of things to say. So for example, I have a client named Mark who has a date tonight, actually. And I was texting him some two or three questions he can have ready to ask his date. His dates, I forget her name, but they were texting about how she played soccer in college.

By the way, if you hear a loud jingly noise, because my cat, Reggie, is playing with a little cat ball, jingly ball. Anyway, so my client, Mark, has a date tonight with a woman who played soccer in college. So what we don't want to do is just have only ask questions like, so who did you play soccer for? What position did you play? Those questions are fine. but we can amp it up a little bit and make it more flirtatious by making the questions more

playful and more emotionally enticing. Flirting is about helping a woman feel emotions, feeling good emotions she wants to feel with you. So with Mark, I was texting him sample questions to bring to the date, you know, to have quote unquote in his back pocket. One of the questions was what was your soccer highlight moment. Oh, what was your sports center soccer highlight moment in college? Having that question ready for him to ask her, because that question prepares her to answer something she enjoys talking about, soccer.

And I gave him a fun, flirty question to have ready to ask her, which is, hey, so you're into soccer, right? If I commit a foul or a penalty on this date, are you going to take out a red card and penalize me? So now that's what I mean by playful. And these are fun, light, playful questions that you can come to a date with. I don't want you to think, like, you have to memorize questions, but it's good to have some backpocket questions ready, just so you're always, you're never going to run out of things to say if you have two or three backpocket topics. Okay, flirting tip number six, no dick picks allowed, unless it's a picture of Dick Cheney.

Flirting tip number seven, tell her she's charming and tell her why. Her laugh, her wit, her intellect, look her in the eye at some point during that date, assuming you like her, and say, you know what's really charming about you? And then tell her what it is, make it authentic. Is it her sense of humor? is it her the way she giggles try to make it a quality like her wit her intellect as opposed to you're beautiful you're pretty you have beautiful smile those things are fine but it's better to tell a woman you like her and are liking her based on traits about her and a great word is charming

if you're really feeling bold really feeling bold you can tell a woman she's sexy use the word sexy and tell her a trait that you find sexy about her. But if that's a bit too scary for you, at least go with charming. That is a clear, direct statement that you are interested in her romantically. And that is one of the core foundational ways we flirt, clear language. Flirting tip number eight, be real, be authentic. Mom was right. Mom was right. Women like you for you. Women like you for you. You are enough. Flirting tip number nine. Information is the opposite of flirtation. Logic, facts, figures, information. That is not flirting. Flirting is emotion. It's play. It's emotion. It's making women feel the feels. Don't be afraid of information. It's okay to find out where she went to

college, what she does for a living, what her hobbies are. But pure information is the friend zone. If you just share information, you are looking at a one-way ticket to the friend zone, which we don't want you to get stuck there. All right. Flirting tip number 10. Women love, love, love, love banter. Banter. How do you banter? Well, a really easy way to start learning how to banter is a playful tease.

And if you tease or bust balls or roast your friends, then you should do the same thing on a date, but do it in a playful way. way. Light, playful teasing. The best way to learn to banter is ask yourself, how do I banter with my friends and bring some of that banter energy to a first date? And a playful tease is a really good way to do that. Okay? Flirting tip number 11, have a staring contest. That's part of that playful philosophy I shared with you. I love doing staring contests on first dates. Look her in the eye and say, okay, let's do a staring contest. The first one who looks away or who laughs loses. And then count down. Three, two, one, go. It's very childlike. It's innocent. But guess what? It gets the two of you making deep eye contact. And as soon as you try to not laugh, of course,

what are both of you going to want to do? Start laughing. That's a great vibe on a date. Flirting tip number 12, here's a simple hack for good date banter. Talk about light topics. Think pets. Do you have pets? Does she have pets? Talk about your pets. Talk about food, favorite foods or least favorite foods.

Of course, talk about travel. You can, one of my favorite topics to bring up on a date is just asking a woman what do you love to do more than anything else? What lights you up? She'll reveal what she's passionate about. And now you have a little window into something she enjoys talking about. So one of the simplest ways to not, quote, run out of things to say, it's not that you need to come with lots of content and planned things to say.

That'll just get you in your head. If you have three or four topics, then the topics will tell you what to say. Here's what not to talk about on the first date, by the way. My client, Brendan, came to me because he was struggling on first dates. And I said, oh, what are some things you talk about on dates? He said, well, I talk about World War II. I talk about when the Germans, the Nazis invaded the Soviet Union in 1941. And I said, wait, you talk about Operation Barbarossa, the largest land invasion in the history of warfare.

That's your first date topic? How'd that go over? I asked him. And he said, yeah, she didn't want to see me again. So here's a hot tip. Maybe don't talk about Adolf Hitler on a date. Just saying. All right.

Number 13. Tip number 13, don't split the bill. Pay the bill. Okay? You're the man. She's the woman. You pay unless you want to be friend zoned. In other words, to pick up a chick, pick up a check.

Flirting tip number 14. Give her fun challenges. on a date. Playful challenges. Are you noticing a theme here? Playful, right? Give her fun challenges. You could say, my client used this one recently who doesn't know TikTok, but he was on a date with a woman who's all into TikTok. He said, okay, explain TikTok to me as if I was your grandfather. And she said, well, grandpa, Jerry, here's how the TikTok works. Or you might look around the room on a date and say to a woman, okay, let's try to guess how many dates that couple is on based on their body language. It's really fun to look around a room and figure out what other people are up to.

This gets you and her collaborating together, figuring out what the vibe is with other people. I was on a date once. This is such a dumb example, but I was on a date once and I swear to God, John Stamos was there. Or at least it was John Stamos's twin brother. And I just was like, oh my God, look at that guy over there. That's John Stamos. And she and I debated about whether that was or wasn't John Stamos. Okay. Flirting tip number 15.

What to say when you approach? Keep it really simple. Give yourself three simple options. Don't try to think of the perfect thing. When you approach, there's no such thing. There's no such thing as perfect, but I can give you a perfect framework. Here it is. Give yourself three options for what to say when you approach.

Option number one is give her a G-rated compliment. option number two is ask her a question that makes sense given the environment she's in or that you're in or option number three is is make an observation and call out what you notice based on where you are so for example you might want to compliment her really cool tattoo or you might want to maybe you're at a coffee shop and you see she's drinking some large fancy coffee drink and you might ask her what kind of drink that is or the third option would be you make an observation I was at the gym once, and this woman had a water bottle shaped like a flask, and it was clear so you could see the water inside. And I said, hey, that's an interesting water bottle.

Is that gin or vodka? So think a G-rated compliment, simple question, or an observation. And that's more than enough to get a good conversation started when you approach. And as a bonus, this is 89% rejection proof. Roughly nine out of 10 approaches will go well from the start if you just simply use that framework. Okay. A flirting move number 16. Don't try too hard to be funny.

It's not that important. Being funny is a nice bonus with women. But lower the bar for how funny you think she wants you to be. If you're funny, great. If you're not the funniest guy in the world, that's okay. By the way, you can learn to be funny. I can help you become funnier. Go to datingtransformation.com.

If you want to book a call with me and I can talk about my coaching and tell you how we can make you amazingly funny if you want, you can learn it. But remember, if you're on a date, it's just a date. It's not a Netflix comedy special. Now, what you do want to do, instead of focusing on trying to be funny or charismatic or giving amazing content, all you really want to do is just make sure your joke is clear. The bar for how good a joke or humor needs to be on a date or with a woman you're talking to, it's a lot lower than you think.

But you do want to make the joke clear. The first rule of humor is just make sure whatever joke you are cracking, it's crystal clear. Okay. Flirting tip number 17. Again, I'm going to repeat something I said earlier, but it's so important. Flirting is not about perfect lines or being cool or mysterious. It's about playfulness, right? In other words, it's not a game of win or lose.

This is not a win or lose thing. It's a game of tag. It's a game of tag. That's my metaphor for this. Let's have fun. Tag, you're it. Tag, you play with me. Tag, now I play with you.

That's what a really nice vibe is in the early part of courtship and dating. Flirting tip number 18, say risky things. be willing to fuck it up. What you think is safe is actually risky because that leads to the friend zone if you play it too safe. And what feels risky to you is actually safe because you're being memorable, you're going out to the edge and you're making an impact. I was on a first date once where I was waiting for a woman to walk into this fun little dive bar I used to go to. and her name is Natalia, beautiful woman, an actress from Europe who had just moved to America to try to make it in American cinema. And she walks into this little dive bar in Chelsea here in Manhattan.

And I'm sitting in a room filled with guys. It just happens to be like, oh, a lacrosse team had just come in to have, I don't know, post-la-cross practice drinks. So she walks in to see me sitting in a small little room, not room, but like a section of the bar with like literally 14 men, young, powerful looking men. And she looks at me and I look at her and she said, oh, what's going on here? And I just said the first thing that came to my mind. I said, oh, I just thought, you know, you might want to have a gang bang with me. I was not planning that. That is a risky thing to say.

Making a gang bang joke, literally the first sentence out of my mouth, I would not advise you or a client to say that. Don't try that at home. But she laughed. She loved it. It said to her, wow, this guy doesn't really care too much. He's just being himself. He's having fun. She laughed and the date went really well.

Anyway, bottom line is, don't play it safe, play it risky. Because risky is actually safe. the sense that it's a safe, smart bet for you to get some good dating results. Flirting move number 19? Should you break the touch barrier? Yes, but go easy. Not every woman likes physical touch. Not every woman wants that. Some do, some don't. So that leads us to flirting move number 20. No creepy touching. Don't leave your hand on her thigh for two minutes without any purpose. Think light, fun, G-rated touching, a high-five, a thumb wrestle, a fist bump. Maybe as the date progresses, you can do things that are a bit more romantic, like

brush the hair out of her eyes. And of course, eventually holding her hand and going for a first kiss later on in a date. Bottom line is no creepy touching. Do not just put your hand on her knee for three minutes. That's fucking weird. Okay. Flirting move number 22. Flirting is innocent, not sexual. I approached a woman named Alexis many years ago. She was walking out of a Forever 21, and I approached her, and I just said, hey, you're adorable. I wanted to meet you. And it went great. Fast forward. A couple dates later, it goes well. She spends the night. The next morning, she says, you know what I loved about how you approached me. It was so innocent. That just felt so good. Now, Alexis said this to me after we had just

gotten done having sex on every piece of furniture in my apartment. We did wonderfully X-rated things for a long time that night. Yet, she just loved how innocent my approach was. So my point here, of course, is flirting is about innocent, G-rated, nice and light early. There will be a time when the time is right for you and that woman to get sexy, but it's not on the approach. It's not the first interactions. Flirting is innocent, not sexual. Flirting move number 23. Flirting is frosting. It is the frosting on the cake, but the cake is you. The cake is that you are enough. You must buy into your worth as a man. All the flirting moves that I could teach you aren't going to work all that well if you are battling a lot of self-doubt feeling you're unattractive

not good enough not whatever not what women want flirting is frosting on the cake but you are the cake okay flirting move number 24 negging is gross nagging you know you know what negging is right old school term to try to make a woman feel insecure so that she'll seek your validation in return, that red pill negging shit, it's gross. Again, I come back to playful teases, right? Teasing is a part of flirting. It's not the only way to flirt, but it's a powerful tool early on. So here's a fun little flirty thing you could say to a woman early on.

You could text her this. You could say it on the dating apps in the first few messages after you've talked a little bit. You could say, you're either the coolest woman I've met in a while. or the nerdiest. I'm just not sure which. Give that a try. It's a fun compliment plus tease,

which is very effective for a lot of women. Flirting move number 25. Text her this cheeky message after a first date. Hey, I just wanted you to know you had a good time last night and you want to see me again. Or you could text her something else. I also like to have my clients message women, And something like the accidental text on purpose, to quote Larry David from a curb episode,

the accidental text on purpose would be something like you text her, of course, after a first date. But the message is, mom, dad, oh my God, I think I met the one last night. I just hope she doesn't find out that I still live in your basement. Anyway, play around with fun, cheeky day after first date text messages. women love it. And it makes it more likely you'll get a second date. Number 26. No sexual talk on a first date. Or at least not in the first half of it. You want to ease into sexual conversation. It's not required on a first date. Optional. It can happen. It doesn't have to. In other words, don't go from zero to 69 in six seconds.

All right. Save sexual talk for down the road a little ways. Flirting move number 27. if she went quiet. If the woman you're messaging, texting went quiet, text her this, Dear diary, cute girl is missing. Send search party? Playful, light, women love it. Flirting move number 28. The secret to teasing, again,

I'm going to repeat an important theme here today. Make it light and playful. How do we make it playful? Well, choosing light topics. when you're teasing a woman on the topic of teasing, never, ever, ever tease her about something that she could get offended about. You know, something personal, right? Like, you know, appearance, wait.

Make it about light topics. Tease her about her favorite, if her favorite band is Nickelback, tease her about that. My girlfriend's favorite band, arguably, is the Spice Girls. I think it's been a while since our first date, but I think I teased her about, you know, Oh my God, spice girls. Oh, man. Why can't I meet a cute girl? It has actually got good taste in music.

Flirting tip number 29, back to teasing, or one more thought on teasing, about what not to do. My client, Nick, once teased a woman about her drinking. Like, she had three drinks on their date, and he joked about her alcoholism. She got offended. No good. I once approached a woman and she had a cute little, she had a tiny little cute little dog with her. I forget the kind, but one's a really tiny little dogs. And I joked that it looked like a rat.

That did not go over well because, hey, a woman's dog is like her child. And that approach did not go well. So learn from my mistakes. Learn from my mistakes. I made every mistake there is to make. All right, flirtatious move number 30. Make warm eye contact, confident eye contact, but not murder eye contact. Don't be Joe from you, right?

Eye contact is powerful. A woman likes a guy who just can look her in the eyes. And the way to make it not too intense is just to have a nice little smile on your face when you're looking at a woman. on a date or an approach or any in-person conversation. All right. Number 31. Use callback humor from earlier in a date.

Callback humor, you might know that term. It's a humor writing term for stand-up comedians or I guess it might be in movies and TV as well. When you call back to an earlier joke that the two of you laughed about. In stand-up comedy, it's when a comedian does a punchline, you know, early in his sense. and then at the end, he calls back to that joke. The audience remembers it, so it hits harder. So you could use callback humor, right? So maybe that, quote, gang bang joke I made,

let's say that deep into that date, I might say, hey, you know what, yeah, we should definitely do a second date. You know, why don't we set up that gang bang for our second date? So I'd call back to the earlier joke. Basically, if she laughed once, call back and make the joke again. Drop it in there whenever the time seems right. But again, don't do gang bang jokes. That was just my story that I wanted to try to convey to make a point.

Number 32, tell dad jokes. Women like it. Dad jokes are innocent and playful and typically will go over really well. So if that's your sense of humor, use dad jokes. By the way, did you hear about the story? Did you hear about the guy who lost his whole left side? He's all right now. Number 33, avoid interview mode by sharing one detail about you for every two questions you ask.

So here's what I mean. I call it the two for one rule. If you're on a date and you notice that you are asking a lot more questions than she is, be aware of that. That's interview mode and that can hurt you. the two-for-one rule is for every two questions you ask her, pause and then share something about yourself. Make a statement and observation, share something from you. Don't only interview her. If you follow the two-for-one rule, you're going to get out of that interview mode.

You'll be interrupting the interview with you actually offering and sharing things. Flirty move number 34. Be clear in your interest. Clarity is so important, right? again flirting is easier than you think i like you can be as simple as that flirting is simple it's scary at times it's vulnerable but it is so simple so be clear here here are two magic words to show that clear interest i want as in i want to see you again or i want to take you on a date or i want you to know that you're fantastic or I want to kiss you. Clarity is powerful. Women want to know what a guy's thinking.

Because here's number 35. Women don't want you to play it cool. They want you to be clear. I like you is all you need to say to a woman to be flirting with her. So don't play it cool. Play it clear. All right. Number 36, lead the conversation.

Dating is a dance. So lead, lead, lead. Women love a man who leads on the dance floor and also the dance floor of dating. Number 37. Do you want to approach a woman? Be authentic. I gave you those three icebreaker options earlier. But if you want to be more direct, some guys just like to say what they mean, walk up to that woman and say, excuse me, I'm actually kind of shy, but I had to meet you. I'm Connell. That's what I'd say. But flirting tip number 38 is just don't call yourself Connell. That one only works for me. Use your own name.

Number 39. Use my texting framework. Play, play, play, play. Pull the trigger. It's a four-step framework. Most of your text messages should be light and playful. Play, play, play. Okay?

Teases, jokes, light questions. Again, play. But you have to pull the trigger. you need to ask for what you want, right? So tip number 40 is keep those texts light and playful. Flirting is about play, play, play, play. But then tip number 41, pull the trigger. In other words, ask her out.

You've got to ask her out. Because if you only banter and play back and forth, but never ask the woman out, then you might fall into that pen pal vibe. And it might be a fun, playful, flirty pen pal vibe that she loves. But women are not going to ask you out, mostly. Mostly. They're waiting for you to be the man. So be the man.

Follow my texting framework. Play, play, play, play. And then pull that trigger. Number 42. Stop texting. How is your day? Start texting. How is your day on a scale of one, two, won the lottery?

In other words, find slightly fresh ways, surprising ways to ask a comment. questions. So no more how's your day. You could say, how's your day on the scale of one to 10. Parentheses, mine is an 8.734-1-2-6451. Or instead of how was your weekend, by the way, that's not going to get you friend zone. Don't be afraid of how's your weekend. But if you do it over and over again, that can be pretty dull. So instead of how's your weekend, you might say, what was your weekend highlight? And give her three options. Hey, what was your weekend highlight? A, Yoga, B, brunch mimoses, or C, best nap ever. Give her multiple choice.

That makes it fun for her to answer you. All right, flirty move number 43. Should you confirm a date? Yes, but don't confirm a date like it's a meeting with your accountant. Confirm it with a little light flirtatiousness, okay? So in other words, here's how you should not confirm a date. Hey, Jennifer, just making sure we're still on for tomorrow at 8. Does that still work for you?

Don't do that. That gives a woman a get out of date card if she wants to play it. Don't do that. Instead, you can confirm a date in a more light, fun, playful way. So, which leads me to tip number 44. You could text her this the day of the date. You could say, hey, just so you know, I look really handsome today. So you better, you better be ready for tonight.

And then her response to that is her confirming. She'll respond with something like, oh, okay, I love the confidence. Boom. She just confirmed the date with you. So you don't want to give her a, are we still on option? Just flirt, send something playful or flirty day of or maybe the day before. and her response is the confirmation, okay? Flirty tip number 45, to avoid the friend zone, go for a kiss on first dates, at least if it's a

nighttime date and if the vibe was good enough. Okay? If it was a pretty good vibe, the conversation was solid, flowed relatively well, go for a first kiss. You are never going to lose a woman's interest in you by going for a first kiss and the cheek, you will lose the interest of some women if you want to do it and don't take the chance because you're not showing that you're willing to go for it. And women want a guy who goes for it. All right. Number 46, two more. Number 46, if you're afraid to go for that first kiss,

don't ask permission. Tell her, I want to kiss you. Look her in the eye and just really commit to it. hey, I want to kiss you. Then if she seems tense, if she looks nervous in a tense way, don't go for it. But tip number 47, if she smiles, if she says something like, oh, really, you do, or something like that, then move in to lock lips. She's giving you that. She has just given you that consent. And then bonus tip, enjoy that first kiss with her.

and after you have that wonderful date, that first kiss with her, remind yourself women like me. I'm enough. I am more than enough. That's proof that I'm enough. All right. Hey, thank you so much for listening today, by the way. If you struggle with what to say and how to flirt, what you can do is go to my website and book a free call to talk to me or somebody from my team about how my dating coaching

works. So you can go to datingtransformation.com, book a free consultation call with myself. and who knows, you and I can talk soon and I'll be helping you one-on-one flirt like you mean it and never running out of things to say and having some fantastic connections with some wonderful women and getting you a great girlfriend. So go to datingtransformation.com if you want to book a call with me and until next time.