How to Get a Girlfriend with Connell Barrett
Use these 8 Flirty Questions to Stop Boring Women and Spark Deep, Romantic Conversations
Tue, 27 May 2025
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 questions, and master texting with a simple 4-word rule. Whether you’re just starting out or stuck in a dating rut, this episode gives you the tools to build real connection—and get the girlfriend you want.You’re About to Learn:01:45: Why Some Women Want to Date Guys with Little to No Sexual Experience08:18: How to Get out of Interview Mode with these 8 Flirty Questions19:30: Why Some Men Become Incels—and How to Avoid this Trap29:11: Your New 4-word Framework that Makes Texting Fun and Effective33:42: Should You Worry if your Girlfriend is Texting Her Ex?Listen now and take on step closer to finding your dream girlfriend!FOR A FREE STRATEGY CALL WITH CONNELL TO FIND OUT IF DATING COACHING IS RIGHT FOR YOU:http://www.datingtransformation.comWANT A FREE COPY OF CONNELL’S NO. 1 AMAZON BESTSELLING BOOK, “DATING SUCKS BUT YOU DON’T”? EMAIL CONNELL AND WRITE “FREE BOOK” IN THE SUBJECT LINE AND YOU’LL GET IT INSTANTLY:[email protected]
Chapter 1: What do women really want in a date?
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. Welcome back to the How to Get a Girlfriend podcast. I am your host, dating coach, Conal Barrett.
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've 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 connell at datingtransformation.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 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 20s, I focused 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'm accepting the Nobel Prize 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.
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Chapter 5: What does it mean to be radically authentic in dating?
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.
It had nothing to do with her. I was actually really very charmed by her. So I just listened and I chimed in and I went into interview mode. But I was asking good interview questions. Here's what shocked me. So the date ends. We say goodnight. 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 slash 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. 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 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 or religion, and I found out she was named after the George Michael song, Faith. Lucky for her. She wasn't named I Want Your 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.
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