Not knowing what to say is the biggest thing that stops you from approaching women in bars, coffee shops, or at your gym. And if you talk to women sometimes, do you flirt correctly? Or do you come off as boring, or even creepy? It’s hard to know! In this episode of the Dating Transformation podcast, dating coach Connell Barrett gives you 10 flirty questions to ask women when you approach, so you can confidently know exactly what to say when you approach… and get numbers and dates. Listen now! And remember to approach with AUTHENTICITY! Because women like you for you.
FOR A FREE STRATEGY CALL WITH CONNELL, TO LEARN HOW TO ALWAYS KNOW WHAT TO SAY TO WOMEN: https://www.datingtransformation.com/contact
GET CONNELL’S NO. 1 BESTSELLING GUIDE FOR MEN, “DATING SUCKS BUT YOU DON’T,” YOUR PRACTICAL GUIDE ON HOW TO GET A GIRLFRIEND BY BEING RADICALLY AUTHENTIC:
www.amazon.com/Dating-Sucks-but-You-Dont-ebook/dp/B08LDZL3
READ CONNELL’S 47 TIPS ON HOW TO GET A GIRLFRIEND
"Syncing with emotions is key. It's about embracing the emotional wavelength—fun and playfulness intertwined."
-Connell Barrett
“Genuine connections thrive when you show interest in understanding her true self."
-Connell Barrett
Connell Barrett, Founder and Executive Coach of Dating Transformation
Website: https://datingtransformation.com
Instagram: https://www.instagram.com/datingtransformation
00:00 - Introduction
01:53 - Mastering Interaction with 10 Key Questions
03:35 - The Key to Engagement06:58 - Love Life Transformation
12:26 - Inquiring About Her Company
13:37 - Turning Misunderstandings Around
17:09 - Breaking Stereotypes
21:54 - Positive Work Inquiries: Elevating Conversations
23:19 - Boosting Attraction Levels25:18 - Outro
Powered by Heartcastmedia
You May Also Like:
Intro:
And at one point, she even said, and I quote, yes. They're real. Here, touch them.
Connell Barrett:
Welcome to the Dating Transformation podcast. Here's your host, dating coach, Connell Barrett. Welcome back to the Dating Transformation podcast. I am your host, dating coach, Connell Barrett. I'm here to help you learn to flirt, gain confidence, and attract a great girlfriend all by being really fake and a creepy pickup artist. Just kidding. Just kidding. It's all about being authentic, being genuine because that's what works. And, I wanna ask you a question. Do you want to flirt with women and ask them some flirty fun questions, but you're just not sure what to ask, what to say, especially when you've just walked up and started speaking to a woman in a venue like a bar or a lounge or a night spot or a restaurant or happy hour? Well, today's today's episode, my mouth does not work well.
Today's episode, I'm gonna give you 10 flirty questions that you can ask when you're just walking up to and approaching a woman, breaking that ice for the first time. If you've never met her before, I'm gonna give you 10 flirty questions, 10 flirty things to ask her. And I'm also gonna help you do this in a way that's not gonna get you stuck in dreaded interview mode. I'll also talk about why and how interview mode happens and how to ask questions in a way that's not like you're interrogating her. So let's do it. Let's do it. Let's get right to it. Ten flirty questions to ask women when you've approached a think bar, club, lounge, maybe happy hour. Here we go. I'm gonna give you 10 questions, and notice as I go, these are not just 10 random questions I've thrown together. I'm actually giving you a cascading maybe escalating is a better term. An escalating series of things to ask that help you get toward a great outcome, like a phone number or a date that you both agree on. So I'm not saying you have to ask all 10. I am saying, however, that notice how we're going from more g rated and friendly to more flirty and leading toward a date or a phone number. So here we go. Flirty question number 1, when you just walked up to her at a bar or a club or a lounge, if you can start literally, the first thing you say is flirty question number 1, which is, oh, hey there.
Are you fun or are you boring? This is a great flirty question to ask as your opener. Why? Well, it challenges her. It subtly lets her know that you wanna hang out with somebody who's fun, that you're not looking for a boring person to hang out with, that you're looking for somebody to have fun to hang out with. And this sends her a really good message that you are not there to be needy, to entertain her. You're there to see if she's up for fun, and that's a good frame to come from. It makes you seem like you are selective. You're trying to find somebody who you'll enjoy, and they will enjoy you. Now what I also like about this question as an approaching opener is that it's a very simple question, and it gives her a very simple choice. She's either gonna say, oh, I'm fun, or she might even say, oh, I'm actually really boring. Either answer is great for you. Here's what you can do to handle it. If she says, oh, I'm fun, then you can say, tell me how. Show me how. How do I know you're a fun person? Now you've got her in a very playful way. You've got her jumping through some fun hoops for you As opposed to what can happen to a lot of guys when they approach a woman is you feel like you're trying to win her over, get jumping through her hoops, trying to show her you're good enough, and it's a much better strategy to get her jumping through 1 or 2 of your hoops. By the way, we're doing this with fun, good intentions.We're not doing this as some kind of manipulative thing. It's more about how you're putting a social frame out there that paints you in an attractive light. So, basically, your vibe is, here I am. Entertain me. And that's something very different. Women don't get that very often. Anyway, if she says, I'm fun, you can say, well, show me. How fun are you? Or tell me.
And then, however, if she says, oh, I'm boring, then you can tease her. You can say, damn it. Why are all the cute girls boring? That's okay. It can be exciting enough for both of us. I'll try my best to carry your load, and that's also a really good thing to say in those first 10, 20 seconds of getting an approach to hook and have her wanting to keep talking to you. Okay. Flirty question number 2 to ask when you approach. You ask her, do you know what's very interesting about you? This is a great approach opener. And it's helpful because what you're doing is giving her a piece of clickbait in real life, in real time. You're basically saying there's something interesting about you. And you're also subtly saying, and I'm the one who has the answer. Everybody in the world wants to be interesting and wants to seem interesting, at least to certain people. And so you're creating an instant moment of, well, what? Tell me. What's interesting about me? You're sparking her curiosity, and you're also making yourself the key to answer the question, how was she interesting? Now in terms of what to say next, you're probably asking, well, a couple options here. One option is you can create sort of a universal answer that you can say to almost any woman. Put it in your back pocket. If you can't think of anything genuinely interesting about her, you can say, well, you carry yourself with a lot of confidence, or you just seem like you have a very adventurous vibe. Most women here don't seem adventurous, but you do.
I'm gonna read your mind. Ready? I'll bet that you would love to confidently approach women. Get great matches on the dating apps, flirt with charm, and attract your dream girlfriend. Right? But fear keeps you from approaching. You're not sure how to flirt. You struggle on the apps, and desirable women just don't seem into you. Well, I have great news. Dating coach, Connell Barrett, can help. He's guided thousands of men like you to more confidence and help them attract their dream girlfriends. So book a free strategy call today to see if Connell's coaching is right for you. On your call, Connell or a team member will give you personalized advice to help you have more confidence, more dates, and more fun. Oh, and you'll be dating women as your best self, a charming gentleman. That's because Connell does not teach creepy pickup artist tricks. He unlocks your most confident self so you can make authentic, romantic connections. Your next steps? Book your free call today at dating transformation.comforward/contact, and grab a time that works for you. Then you'll be on your way to more confidence, better results, and attracting bright, beautiful women. Oh, so you know, soon Connell will stop taking on new clients. So book a call today while you still can. Go to dating transformation.com forward slash contact and transform your love life. Bye.
Now those are basically boilerplate, one size fits all statements. I'm not a big fan of scripted content. I'd much rather you just get real, get present, get in the moment, and let it come out of the moment because that's what's gonna bring out your most authentic and attractive side. But if you can't think of anything else, you can use one of those answers. Also, what I love to do is say that you're your interesting opener, and then I have no idea what I'm gonna say to justify it. And that's really fun. It's kinda like walking on a high wire. It can make you feel a little bit dangerous, but in an exciting way. So feel free to test that out. Walk up. Hey. You know what's really interesting about you, miss? What? What's interesting? And then your brain is gonna figure it out. This is something I learned from taking improv classes. You go up there on stage. You don't know what you're gonna say, but you're gonna figure it out once the audience is paying attention to you, and you're gonna figure something out when she's paying attention to you. Give that a try.
Okay. Flirty question number 3 to ask a woman when you approach. Here's another good opening line. I need a woman's opinion. What do you think of my style? And then you might ask her about your leather jacket or the shirt you're wearing or your shoes. This is a really good icebreaker because almost every woman out in the world wants to be an expert in something like style, clothes. I'm sure she puts a lot of time and effort into her style, and you can be darn well sure she notices what men wear and she notices good style and bad style. So you could ask her a genuine question that makes her an expert on your style. And this can lead to a great flirtatious comment because she might then give you a compliment on your awesome outfit, your shirt, your shoes, your cool belt. Or get ready. She might give you some real feedback and say, well, I don't know about those khaki pants, dude. I'm not really loving those khakis. And, she might give you some real feedback, which can actually help you style wise. But most importantly, you've done the most important thing that an opener is designed to do. You have started a conversation with a woman who you had not previously known, and that's a plus. That is a big win. Okay. Flirty question number 4. When you have approached a woman, after you break the ice and you're chatting for a minute or 2, get her name and then ask her, what's the story behind your name? Her first name is her favorite name in the world. It's her favorite word in the world. Everybody feels that way. We all love the sound of our first name. She's gonna like talking about her name, and this is a great thing to keep the conversation going in an area that she's interested in. I was out recently with my client last weekend in New York City, and he met a really cool, cute girl, and her name is Faith.
And he asked her because I told him to, hey. What's the story behind your name? And she lit up. She smiled. And she told this great story to my client about how her parents are big George Michael fans, and she was named after the George Michael song, Faith. And I was literally standing by him, what, listening to this, and I leaned in and whispered in her ear sorry. Whispered in his ear. I said, tell her that it's a good thing that you weren't named. I Want Your Sex, another George Michael song. And then he said, oh, it's a good thing you weren't named, I Want Your Sex, and she busted out laughing. So think about this. In 2 minutes, he had gone from, hey. How's your night? Joking about her name being called, I want your sex, and she was laughing her butt off. And they were having a great conversation, a great flirty conversation. Alright. Flirty question number 5. When you have just approached a woman, ask the question, who are you here with slash how do you know each other? This is not a flirty question per se, but it is so important because you need to understand the dynamics, the logistical dynamics of the person or people she's with so you know then how much you can or cannot flirt.
You need to know if the woman she's with is her friend or her roommate or her sister or her girlfriend. You need to know if there's a guy in the mix. You need to know if he is a boyfriend, a brother, a gay friend, a random dude she just met. So you always wanna ask every woman who you just met and approached. You wanna ask her, who are you here with slash how do you know each other? Because this gives you valuable intel. Here's a quick story to show you how incredibly valuable this can be. I was once out with my client, James, and James and I were on a rooftop bar in New York City. And James and I started chatting with this beautiful woman in a red dress named Annabella. Lovely, stylish, cool, smart, woman of, Latina descent, if I recall. And James was talking to her. The thing is Annabelle Annabella and Annabelle was with a man. She was with a very handsome, well dressed dude. And my client, James, and I assumed she and he were a couple. We just assumed, but we didn't know for sure. So James actually didn't even wanna approach, and I said, hey. Let's talk to them anyway. You never know. And then a few seconds in, James says, how do you 2 know each other? And she said, oh, this is my brother. Now we're in business. I spoke to my brother. James and Annabella talked to each other, and now I knew that, hey. This was not a boyfriend. This was not a guy who's gonna get pissed off, or at least it wasn't a guy who's gonna be romantically jealous. It turns out the brother was a great guy, an Iraqi war veteran, a great dude who just told some great stories about being in the service, and he had no problem with his sister chatting up with my client, James.
And, also, there was one moment when James and Annabella had been behind me and her brother. In other words, her brother, they had his back. He could not see them. And I could see them. And I look behind me, and I see that James and Annabella are basically making out. And at one point, she even said, and I quote, yes. They're real. Here. Touch them. And she takes James's hands and places them on her chest. Again, never do that to a woman unless she invites you to. But my point is we went from not even approaching that couple, potentially, because James assumed they were a couple, to walking up and saying, hey. How do you guys know each other? And then it turns out he was just a cool dude who was her brother, and James and Annabella fell in love that night, or at least fell in love for that night. And it all started with making sure we asked that question. Rejection, ghosting, loneliness, lack of dates, and lack of confidence. For many men, dating just sucks, but it doesn't have to. There's a simple yet powerful way to gain instant confidence and attract a great girlfriend. Be radically authentic. It's all laid out in the number one Amazon bestselling book. Dating sucks, but you don't. Your step by step guide to attracting wonderful women and doing it with total authenticity. Author and dating coach, Connell Barrett, has had and fixed all the dating problems that you struggle with.
He's also helped thousands of men gain confidence and find love. He's put his best tips and strategies into dating sucks, but you don't, so that you can confidently approach women and get dates. Become magnetic and attractive even if you're not tall or great looking. Always know what to say to make sparks fly. Get lots of great matches and dates on the dating apps, and attract your dream woman. You can find dating sucks, but you don't on Amazon or wherever books are sold in paperback, Kindle, and audiobook. Get Dating Sucks But You Don't Today to transform your confidence and find your dream girl. `Okay. Flirty question number 6 when you're approaching. This is a 2 parter. Where are you from? Then let her answer. And then, oh, is it true what they say about girls from the place where she's from? So, for example, I walk up to a woman I just did this last week with clients. I walked up to a woman. I'm doing some demonstration approaches. Oh, hey.
What's going on? Blah blah blah. Hey. Where are you from? She said, oh, I'm from New Jersey. And I said, oh, is it true what they say? I'm about girls from New Jersey. And she said, what? What do they say? And then I said, oh, I knew it. That proves it to me. It is true what they say about girls from Jersey. And she said, tell me, what do you mean? And this is a fun question to ask early in an approach where you're taking a common get to know you kinda boring question, where are you from, but you're adding some spice to it by making a fun stereotype or a fun assumption about what that means. The bottom line is I don't know what they say about girls from Jersey. Who knows? Maybe they have big hair. They all love Jersey Shore. They all have tattoos of Springsteen on their lower back. I don't know. Every Jersey girl's got her own story. But what you wanna do with this is just know that you can ask a kind of a seemingly boring get to know you question like, where are you from? And then after she answers, you can spice it up with, is it true what they say about girls from blank? And then if she says, what? What do they say? Which she will. You're creating curiosity.
You're sparking her interest. Then you take her questioning answer as the reason that you know that now you know that she is that it is true what they say. Uh-huh. I knew it. I knew it's true. I could tell. And this makes a woman just kinda get curious and more intrigued about what you're talking about, and then that can make her chase your answer a little bit. So you might have heard, like, how to get a girl chasing. Well, this is one of those ways to get girls chasing moves if you ask her if it's true about what they say about girls from her again, whatever her home state is or whatever city she was born in. I usually go with the state. Like, oh, where are you from? Where'd you grow up? And she'll usually say the state or the city. And I'll be like, oh, no way. Is it true what they say about girls from Texas? What? What do they say? Oh my god. It is true what they say. I can't believe it. It is true. You're proving it to me. She's like, what? Tell me. Like, you know. You know. So, anyway, you don't even have to tell her what it is. If you can come up with something, that's fine too. If you come up with, oh, well, is it true that you rode a cow every day to school when you were in grade school. That works too, but you don't have to come up with great content.
You just have to spark her curiosity. Okay. Flirty question number 7 to ask a woman who you've just approached. What do you do for a living? I mean, besides making charming men come and flirt with you. Boom. This one is great. Remember, what we wanna do with an approach is you wanna make it clear that you're not just you're not only there just to talk and be friendly even though that's part of it. You wanna let her know that you're flirting with her. You are romantically interested or at least intrigued. And this is a great way to take a boring question and turn it into something a little bit romantically spicy. Because every guy asks, what do you do for a living? You're gonna be the guy who says, hey. What do you do for a living besides getting charming men like me to come talk to you and flirt with you? And this gives her the gift of clarity. You're letting her know you're flirting with her, which is nice. Women like having a guy who's confident enough to just put it out there. And, also, you're then letting her sort of answer in a genuine way and actually learn a little bit about her, like, what she does for a living or what she does for fun besides getting men coming to talk to her. So this is a great question to amp up that flirtatious vibe.
Okay. Flirty question number 8 to ask after you've approached is what do you love most about your job slash career? What do you love most about it? Again, the secret to flirting or the secret to successfully communicating with women, so much of it is just getting on an emotional wavelength. It's emotional. It's fun. It's playful. There's emotion there as opposed to pure facts and figures and logic. So most men, when they talk to a woman, they might say, how long have you been in this career? How long have you worked there? What is your job duty? What do you do? But you're not just settling for that. You're saying, what do you love most about it? So this lets her give her permission, and you not just permission. You are basically asking her to talk about her work in a positive, emotionally evocative way rather than just asking a boring question. Bottom line is before you ask a woman out, we wanna know genuinely who she is, at least a little bit of her. She's not gonna give you her number. She's not gonna go on a date with you, probably, unless she knows that you are a guy who's gotten to know a little bit about the real her. Okay. Flirty question number 9. Are you more of a classy cocktails bar girl, or are you more into fun dive bars? I love this question because now you're seeding the idea of a first date inside of a flirty question. Are you more into classy cocktail bars, or are you more into fun dive bars? You're basically priming her to get ready for you to ask her out, and you're also getting her to collaborate with you and, essentially, telling you the kinds of places she actually likes to go and wants to go for a date.
And she's gonna choose one of these two options. Let's say she goes with the cocktail bar option. Great. Then that leads to the next flirty question, number 10, which is great. Let's go to a let's find this a great classy cocktail bar. What's your next free night? And then you set up the date that way. Or if she says a cool fun dive bar, you say great. Let's go to a fun dive bar. I have a couple great options. What's your next free night? And then you set up the date that way. Notice the power here in these questions. You are asking her which of these two things she likes to do, but then you're assuming she wants to go out with you. You're saying, when are you free next as opposed to sheepishly saying, so do you wanna go on a date with me? You don't have to if you don't want to, but do you maybe want to? It's like, no. You're assuming she wants to go on a date with you. If you assume she's attracted to you and you talk that way, you're gonna make a lot more women attracted to you because they like how confident they are. They like how borderline presumptuous you are about her interest in you, and that alone makes her more attracted to you.
So those are the 10 flirty questions from literally that first approach to setting up the date. Go back and listen to this. Did you notice how, again, I had escalated here from that simple first opening line all the way to great. Let's go on a date. What's your number? So I'm not saying you literally have to ask all 10 of these questions, but notice how we stair stepped. One step at a time from, hey. I'm talking to you for the first time, great. Classy cocktail bar drinks it is. What's your number? When are you free? Boom. Date done. This is how it's done, guys. This is how it is done. Alright. In the next episode, we got a lot more flirty questions to get to, and we're gonna talk about first dates next time. That's it for today's episode. Remember, your future girlfriend, that dream girl who's gonna change your life. She's out there. She already likes you. She just has to meet the real authentic you. Till next time.
Thank you for listening to the dating transformation podcast. For lots of free tips, videos, and other goodies, go to datingtransformation.com. See you next time.
Powered by Heartcast Media.
Welcome to the Dating Transformation podcast. I'm coach Connell Barrett, and I help men build confidence + connect with women by being their own authentic selves.
NYC Dating Coach Connell Barrett
106 W 32nd St, New York, NY 10001