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8 Tested Tips to Escape “Interview Mode” on Dates and Create a Connection

Featuring NYC Dating Coach Connell Barrett
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Have you ever fallen into “interview mode”? That’s when you ask your date lots of boring questions (“How was your day? What’s your job? How many siblings do you have?”) that lead to bad dates. Instead of connecting with her, you interrogate her. And there’s no second date because she “just didn’t feel a connection.”

Interview mode is frustrating, but you can fix it… TODAY! In this episode of the Dating Transformation podcast, dating coach Connell Barrett shares 8 tested tips to help you become magnetic to your next date, so you can spark a romantic, authentic connection… and get her asking YOU questions.

Listen now, to make your next date great.



"It's OK to ask her questions on first date. Just ask the RIGHT questions, or else you'll bore her, and there will be no second date."

-Connell Barrett

"Be true to yourself and find the emotional connections we all share. We have more in common than we realize"

-Connell Barrett

Featured in the episode

Connell Barrett
Founder and Executive Coach of Dating Transformation


00:00 - Introduction
00:47 - Breaking Free from the Interrogation Mode
02:40 - Overcoming Interview Mode Misconceptions
07:18 - Creating a Connection on the First Date
11:18 - The Art of Asking Good Questions on Dates
18:17 - Bonding through Shared Passions
22:10 - Teasing Playfully: Sharing Concert Experiences
23:49 - Connecting through Childhood Tales
26:00 - Asking Game-Changing Questions on First Dates
27:21 - Building Trust and Connection: The Power of Questions
27:53 - Outro

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Related Episodes:

How To Make Her Your Girlfriend

How To Make Dating Fun

Great First Dates


Connell Barrett:


Welcome back to the dating transformation podcast. I'm your host, Connell Barrett, helping you attract incredible wonderful women, learn to flirt, and get a great girlfriend. All by being radically authentic. You're the best you. No sketchy pickup artist moves needed, and no fake alpha male, be needed. You don't need that. You are enough. Girls like you for you. And today, I wanna help you fix one of the biggest problems that men struggle with in their dating lives, which is If you're like most guys, this has probably happened to you. You've fallen into direct interview mode on dates or when talking to a woman or texting Interview mode, quite unquote, is a big problem that holds a lot of guys back. It might hold you back. Because what happens is you're not sure what to say. You get stuck in your head, and because you don't know what to offer, you don't know what to say about yourself or how to flirt, you end up falling back into the comfortable zone of just asking her questions, and that can lead to a lot of sort of conversation fine, perfectly fine conversations for states that go okay. Where the conversation flows, you ask if she answers, but it ends up feeling more like an interrogation. You don't wanna interrogate a woman on a date. You don't wanna be like an NYPD cop asking her questions in the backroom.


Where were you on the night of July 14th? What do you do? Where were you born? How many brothers and sisters do you have? You don't wanna get stuck in interview mode because it doesn't create that mutual spark that you and she wants to feel so then the problem with interview mode is you know you're in it, but you don't know how to get out of it. So today, I'm gonna help you get out of the quote, unquote interview mode. First, we're gonna look at what interview mode is. Why does it happen? I'm also gonna puncture a big myth for you about interview mode and actually let you know that it's not always a bad thing. And then by the end of this episode, you're gonna get 8 really good questions to ask on dates that are not interview mode in the sense that it's gonna hurt you. These are 8 great questions to ask on a first date. So let's get into it. Let's talk about the problem of interview mode. Because if you're like most guys, you meet her, You're having a drink. You're getting to know each other, and you just catch yourself falling into that question, question, question, mode. and it becomes less of a date and more you interrogate her, like you're an investigative journalist. or an attorney in a courtroom interrogating a witness. And that is not the vibe we want on a date. And that can really hurt your confidence. It can lead to the friend's own. It can lead to hearing the dreaded. Hey. It was nice meeting you. You seem like a good guy, but I just didn't feel a connection. So that's what inter-interview mode can do to you. But here's the thing about interview mode. And I really wanna make this clear. Most everybody gets interview mode wrong. Here's the big myth about interview mode. The interview mode itself is not a bad thing. What I mean is it's not a bad thing to ask women questions on dates. In fact, it's weird not to ask questions. Ignore those pickup artist guys who say only make statements, only be an alpha male, only state make statements, and avoid questions, That's bullshit. Humans ask questions. We do it all the time, especially to people who are getting to know each other. So don't be afraid of asking questions. Here's really what interview mode is. Interview mode is asking boring or logical or informational questions. repeatedly and not offering anything about yourself. So don't be afraid of asking questions of her as long as they're good questions, and as long as they're questions that you then answer about yourself. So here are two rules to smash you out of interview mode. Avoid logical informational questions and instead, ask more emotionally charged questions. So for example, instead of how long you have been at your job, that's informational. Ask her, what do you love most about your job? What lights you up about your job? That's emotional and more compelling to women. Or instead of where did you grow up? That's informational, you might instead ask, oh, you grew up in x, y, z place. What was that like? How did you feel about growing up in Southern California? What was it like growing up in Ohio? Did you love it? Did you hate it or both? So you wanna tap into emotions. So interview mode is asking repeated, logical informational questions. Getting out of interview mode, asking good questions is gonna be asking more emotionally charged not not necessarily romantic questions, but emotionally charged questions. And the second rule you can use to smash out of interview mode is anytime you catch yourself asking repeated questions. Take a moment, check in with yourself, and answer that question that you asked her. as if she had asked you the same question because even if you get into that nice sweet spot of good, fun, flirty emotionally charged questions, you still don't wanna ask 10 in a row without ever asking anything or, I should say, without ever offering your own answers to those questions. So if you've noticed that you just asked her, hey. What's your favorite movie ever? What TV shows do you like? What's your favorite drink? If you catch yourself asking repeated questions, good or bad questions, take a moment and say, hey. What's my favorite show? and then offer that opinion to her about your favorite TV show as if she had asked you. because we want to make sure that we're giving an offering in our conversations with women on first dates just as much as we're asking her to carry that load. We want it to be roughly 5050, 6040 back and forth between you and her sharing about each other. So we're gonna go a lot deeper in a second, but that's the cliff notes version of how to get out of interview mode. Ask emotionally charged questions instead of logic. and then answer any question you ask her, take a step back, catch yourself falling into the interview pattern, and then answer that question. yourself. Okay. Let's go a little bit deeper on this whole topic because



I wanna tell you a quick story about having a first date many, many years ago. I had a first date with a wonderful woman in March. I met on the app Match, and I just wasn't. I had a big epiphany that night. And I wasn't. I really wasn't in a super talkative mood in terms of I wasn't feeling really outgoing. I wasn't feeling really charismatic. And so I mainly asked her questions. And that's not necessarily a good dating strategy. But if you're asking good questions, it can actually be a great dating strategy. So I had a first date with this woman named Rebecca, and I just said I just was I guess I was tired. Maybe I was a little bit in my head, and I just mostly focused on trying to find out what makes her interesting. Trying to find out what makes her fascinating. And in my previous career, before I became a dating coach, I was a magazine journalist. An interviewer, so I got really good at interviewing people. And finding out what makes them tick and asked them good questions and that served me a lot with this date. And I remember we had a 2-hour date, and I basically shared next to nothing about myself. Little bit little bits and pieces, but mostly it was me asking Rebekah all about her career, what she loved about it, helping her tell stories about her family, learning what she was like as a kid, asking really fun, silly questions, which I'll share some at the end of this podcast, but, like, questions like, okay. What actress would play you in the movie of your life? like, really making her think in a fun, compelling way. Frankly, I just didn't have the energy that day or the inclination to offer my own authentic personality and self. So I just let her do most of the talking. And I thought it was really interesting because as we were texting no. She texted me on the way home. We said good night. We had a nice kiss good night. And she later texted me that night. She said, "I remember the text vividly." She said you're the most interesting person I've met in a long time, winky face. And I remember looking at that text and thinking, I didn't say anything about myself. I said I shared next to nothing about myself. What she found interesting about me was that I was finding out what was interesting about her. So I was making her feel special, connected, interesting, and fascinating because I was asking good questions that helped her to feel that way. So I did technically, I did kind of interview her. But it was an interview mode because I was asking good questions, so I'm gonna share a bunch of what some of those are. And I guess what I'm trying to say here is don't be afraid of asking questions as long as they're good questions, as long as they're not relentlessly informational logical questions. And as long as you offer good thoughts about yourself or good information, opinions, and feelings about yourself, and basically show her a window into your life. I actually didn't do a good job on that date. But because she was meeting the authentic me, the authentic me is a very inquisitive person. I like to find out what makes people tick. And because I was talking about her favorite subject herself through the lens of good emotions, the lens of finding out who she is, what makes her tick, I became really interested in her. So don't be afraid of questions, be afraid of logical, boring informational questions and only ask those. That's interview mode. That's the friend zone. That's the first date. death. Let's talk about the art of asking good questions. In fact, Okay. Let's get into this. Let's talk about the art of emotional connection and how to emotionally connect with a woman by asking her the right question. Here's how you do it. This is all there's a whole chapter about this in my book. Dating sucks, but you don't. And I wanna but I wanna give you the very best tip right here right now. So here's how you wanna create. Here's one way to create an emotional connection with a woman. So here's my favorite first date question to ask, and how to use that question to act to create some emotional commonalities. The question is this. Here's something I pretty much asked every woman I had a first date with in some way, shape, or form. The question is, what lights you up more than anything else, and then you listen to her answer, and then you ask her why? Why does it light you up? So it's really a 2 part question. What lights you up more than anything? And then the follow-up question is why? Or put another way, it's, well, how does that thing make you feel? That thing that lights you up. And then what you do as a man is you're listening to her, of course. You're finding out what she loves to do in life more than anything else. And then you're listening to what that vehicle makes her feel, and then you look in your life, you look into your life for something that makes you feel the same way, and then you let her know that you totally understand how she feels because you feel the same way when you do x, y, z. Even if her vehicle for feeling lit up and amazing is different from your vehicle for feeling lit up and amazing, you're gonna be feeling the same way. And that helps to create an emotional connection with women. Let me give you an example. Shortly before the pandemic, I had a first date with a woman I met on dating apps, and I'll call her Jennifer. And Jennifer and I are on a first date, and Jennifer is somewhat younger than me, a slightly younger generation. So she and I could tell that going into the date she and I weren't gonna have a lot of commonalities in terms of specific music we both listen to or, like, perhaps movie, music. I wasn't expecting us to have a lot of commonalities just because she's in her mid-twenties. And at the time, I was in my late forties. So here's the thing about 1st dates. You don't need to. It's a nice bonus if you have commonalities if you both like the same band or the same TV show or grew up in the same state. Those are nice bonuses, but they're not required to create some emotional sparks. So I had this first date with Jennifer, and at one point, I asked that question. I said, hey. What lights I'm just curious about. What lights you up more than anything? What do you love to do more than anything else? and she thought about it. She said, well, I love to paint. She does painting, and she does sculpt sculpture. And I said, okay. Cool. What is it about painting and sculpture that you love? In other words, what is it? How does it make you feel? And she took a deep pause and thought about it. I don't think anybody had ever asked her this. And she said, well when I'm painting and doing sculpture work, I feel like time really stops. I feel really creative. I'm accessing the creative side of me, and she said and I just feel like time stops. and I just get lost in the moment and just lost in that creativity. And then what I did is I went into my mind, my heart, and said, what makes me feel that way? By the way, I cannot paint. I've never sculpted in my life, so I don't have that surface-level commonality. But what I do have, like, all of us have is we all have emotional commonalities. And so I went into my mind, and I thought, okay. Well, what do I do that makes me feel really creative? what makes what gets me lost in the moment, and I went to my thought was improv. I do improv comedy musical improv comedy mainly. And I said, oh, gosh. I feel exactly the same way, or I feel really similar. because when I'm doing improv, I'm being so creative. 20 minutes goes by, like, 2 seconds, and I just feel like I'm so in my body and, like, in the moment She said, yeah. I feel the same way. I'm in my body when I'm painting or when I'm, like, sculpting clay into a pot or into whatever she's sculpting. And I think I probably said something like, oh, yeah. I hear you. I'm, like, sculpting the scene sculpting a funny comic set piece with my scene partner. It's kinda like sculpture. I was really leaning into the sculpture thing. and we really clicked and connected. And we had a great date, and we dated for a while. The pandemic sort of ended it, but that's life. And so This woman with who I didn't have a lot in common, surface level, what I did is I asked you the what lights you up question. Because when somebody finds out what really lights somebody up, they're basically telling you what makes them tick, what makes them who they are as a person, what makes them feel incredible. And so that's my favorite first date question, what lights you up? And then the important follow-up to that is and how does that make you feel? Why do you love to travel? Why? How do you feel when you're skiing? Basically, the follow-up question is how do you feel? Hope that makes sense. So that's something you can do every day. So, again, the steps are to ask her what lights her up, and what she loves to do.



Listen, say why. What is that? How does that make you feel? And you're listening to the emotional reason she does that thing, whatever it is, whether it's painting or sculpture or travel or kickball or closing a case in the courtroom if she's a lawyer or operating if she's a doctor or dancing if she's a dancer. And then you're listening and then you wanna go into your mind and say, hey. What makes me feel very similar? And then you too get to authentically connect over 2 completely different vehicles. So improv comedy, in my case, and painting sculpture for Jennifer, are 2 very different things, but we have the underlying emotional commonality. That's my favorite first-date question. and it's something to work on and explore, and it's what I love about this is that you're your yes, you're doing a little bit of investigation into kinda who she is and what makes her tick, but it's totally real. you're actually finding out who she is as a person and relating it back to who you are as a guy. And then when the sparks the romantic connection happens. It's happening organically in that real genuine authentic way as opposed to just trying to be who you think she wants you to be. You don't have to do that. You get to authentically be you, and just find out the things you share emotional commonalities because the bottom line is there's really only a handful of emotional commonalities, and we all share them. Right? There are certain things in life that make you feel creative and her. Certain things in life that make you feel connected to yourself. or connected to others. Certain things in life certain things in life that give you, like, a peak experience and make you feel excited and sort of turned on emotionally. So the vehicles that make these things happen are not nearly as important as the underlying emotions. So that's my favorite game-changing first-day question, the what lights you up question. Here are 7 more. Here are 7 more fantastic first-date questions. And to get out of interview mode, Again, don't be afraid of questions. Be afraid of logical informational questions. So feel free to ask any or all of these questions on a first date. The most important thing is that other than asking these questions, the other thing you wanna make sure you do is that you answer any or all of these questions yourself. So don't just only ask her these 7 questions. Ask her I should say, ask her and then listen, of course, and then feel free to then tell her your answer to these same questions. That way you're giving. You're adding feelings, thoughts, information, and your true self to the date just as she is. and then both of you are putting your awesome authentic selves out there. Here's so here are 7 great first-date questions to get you out of that informational logical friend zone that comes from quote-unquote interview mode. Here we go. Number 1 is What's your dream travel destination? because, hey, everybody likes talking and traveling. Every woman has an answer to this question. Hopefully, you do as well. What's your dream travel destination? Feel free to answer that and follow that up with the question. Why? Why is it Hawaii? Why is it Sweden? Why is it Newark, New Jersey? Not just kidding. Nobody wants to go to Newark, New Jersey. Okay. Yeah. Next question, number 2, is who should play you in the movie of your life? What a fun, unusual question. Who should play you in the movie of your life? See, this question caters to your date's ego, And whatever actress she chooses is gonna clue you in on how she sees herself. And, of course, you would then say, who should play you in the movie of your life? I don't know about you, but clearly, the guy who should play me in the movie of my life is Brad Pitt. you know, he would just have to dye his hair ginger. Okay.



The next question is who did you see for your very first concert? I love that question. That's a great question because music is a great date topic. So prepare to be super impressed when she mentions Beyonce or really sad teases. tease her joke a little bit if she's you know, her first concert was Nickelback. God forbid. Next question. Number 1, 2, 3 no. Number 4 of our 7 great first aid questions is what was the best day of your life?



What was the best day of your life? Now this question is a powerful one because it takes your date back in time to a big life moment. that if it's her if it's the best day of her life, she's gonna love reliving. And it's also gonna take things way deeper than just a service-level chat. By the way, I would hold off the What's the best date of your life question until a little way into the date. Right? Don't walk in. Give her a hell of a hug. Say, hey. Nice to meet you. Grab a seat. What was the best day of your life? No. Don't do that. Wait. Get into the moment a little bit, and get some rapport going. Ask a couple of lighter questions, and then you can ask this question. Okay. The next one is what do you love most about your job slash career? What do you love most about it? This one lets you both talk about your work in a positive, emotionally evocative way. Again, rather than boringly asking, what do you do? So, again, information and logic are dry and often boring. Emotions are what women wanna feel, and frankly, they're what you wanna feel. So don't just settle for what you do. It's fine, it's fine to ask that question. Don't get me wrong. Don't be afraid of what you do. But then follow up with this question, number 5. What do you love most about your job career? Why do you love it so much? And then, again, be ready to answer that question yourself and be ready to answer it in an emotionally compelling way. In other words, give some deep emotional reasons why you love what you do. First date question number 6, what were you like as a kid? What were you like as a kid? Sharing stories from childhood offers her a chance to be vulnerable to tell funny stories and herself as well. I had one date during the pandemic, just one. I just needed to get out of my house and talk to another human being. It didn't go very far. I think we both were just lonely and wanted to talk to another human. But I asked this question about my date, and it led to this really funny story where she talked about when she was a kid, she loved Halloween. And one for Halloween at school in 4th or 5th grade, she got dressed up as a clown. big red nose, big floppy shoes, the whole red wig, the whole clown look. And she went to school to dress up for Halloween Day. And she gets to school and finds out that she had the wrong day, and she was the only person dressed up. And she spent the whole day just as a clown. It just led to a really funny story. And instead of just an informational question about, oh, where did you grow up? How many brothers and sisters do you have? A much better question is, what were you like as a kid? And here's one more. The 7th fantastic first date question is, what is your hidden talent? What's your hidden talent? Or what are you really good at that most people don't know you're good at?



This allows her to show off a little bit. lets her kind of brag. You're giving her permission to brag and show off a little bit while also revealing a secret, which builds trust, sharing secrets, especially light fun secrets, not heavy, sad secrets, but light secrets. Like, what's your hidden talent that builds trust? And, again, be ready to answer any of these questions yourself. If she's got relatively good social skills, she'll probably just turn the tables on you and say, hey. Well, what's your hidden talent? What were you like as a kid? And that's nice. You're helping her ask you questions as well. But even if she doesn't literally ask you these questions, you can always say, oh, cool. Your hidden talent is doing an impression of Shrek with your Scottish accent, great. Here's my talent. So be ready to answer these questions yourself. Okay. Those are the 7 fantastic first date questions along with that game-changing question that I ask every first date. about what lights you up more than anything else. And, yeah, just to recap here, remember, interview mode It's not asking questions that are bad. It's repeatedly asking logical questions and never offering anything about yourself. That's interview mode. To get out of it, ask these good first date questions, ask emotionally compelling questions, and also answer these same questions. so that you're both sharing and contributing to the date. So these aren't just questions to ask her. These are also questions to ask yourself. And do this, and you're gonna be out of the interview zone, out of the friend zone, and you're gonna have some really good first dates where some sparks are gonna fly. Okay. That's the end of today's episode. Thank you so much for listening till next time. Don't forget. women are not there, they already like you. They wanna date you. They wanna be your girlfriend, some of them. They just have to meet the real authentic you. See you next time.



Produced by Heartcast Media.


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Dating Tranformation with Connell Barrett

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.

dating sucks but you don't #1 Amazon bestseller

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NYC Dating Coach Connell Barrett

106 W 32nd St, New York, NY 10001

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