If you’re like most single guys, you’re not sure how to be fun on your dates or when talking with women you’re into. What do you say? How do you make her laugh? What if you seem boring and she loses interest? Sadly, if your date or conversation is dull, she won’t be attracted to you—and you’ll be missing out on romance.
So let’s amp up the fun factor.
In this episode of the Dating Transformation podcast, dating coach Connell Barrett shares 5 tools you can use to make your dates and conversations WAY more fun. Also, he’ll give you his No. 1 favorite game to play on a date, and it’s sure to get you both laughing and having a blast.
It’s time you STOP hearing women say “I just didn’t feel a spark” and START hearing them say, “Last night was fun! When can we go out again?” Listen now, because Cyndi Lauper was right: “Girls just wanna have fun.”
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
"Cyndi Lauper was right: Girls just wanna have fun. If she has fun with you on a date, she'll want to see you again."
-Connell Barrett
Connell Barrett
Founder and Executive Coach of Dating Transformation
Website: https://datingtransformation.com
Instagram: https://www.instagram.com/datingtransformation
00:00 - Introduction
01:45 - Creating Laughter and Fun for Unforgettable Moments
03:35 - Mastering the Art of Making Dates More Enjoyable
08:13 - Success Through a Playful Approach
12:25 - Focusing on Positivity and Meaningful Conversations
14:34 - Unlocking Romance Through Emotions and Passions
18:20 - From Boring to Exciting: The Power of Fun Topics
22:45 - Choosing Enjoyable First Date Activities
26:50 - Sparking Conversations with Fun First Date Questions
30:01 - The '5 Questions Game: Getting It All Wrong
33:46 - The Art of Pretending and Posing Questions
35:09 - Turning the Tables: Trick Questions and Victory
39:17 - Revealing Nature Through Trick Questions
40:40 - Fun Questions and Game Recommendations
41:23 - Outro
Intro:
Cindy Lauper was right. Girls, they wanna have fun.
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, get a lot more dates with women you're into, and attract a really wonderful girlfriend. And do this all with authenticity. Radical authenticity. No pickup artist Nonsense. And not just surface level. What to say, here's how you know, here's a prescripted line. I'm talking about lighting women up by conveying your best, most confident, and authentic self. And today's topic is how to have fun when talking with a woman you're attracted to, primarily on the 1st or second date, but also in a conversation when you've just met her. Maybe you're at a bar, at a party, some kind of social event. And you're speaking to her and you're thinking, what do I say? How can I make something good happen romantically here? That's what today's episode is about. So I'm really excited about it. It's really all about one of the most underrated aspects of dating. But arguably, the most attractive energy to create with a woman when you first meet her, which is simply fun. Having fun, me. Laughing, joking, creating good fun emotions. You might be a guy who thinks, oh, you've Gotta be tall, handsome, really funny, and witty, and know the perfect thing to say in order to create a spark with a woman. And those things are bonuses. If I mean, any of those things could be valuable, but for my money on a 1st date or that 1st conversation, I just wanna give her a fun experience. I want to give her a fun experience instead of a boring one. Instead of some weird sketchy creepy I'm hitting on you vibe, I just want her to have fun with me. Because if she's having fun with you on that 1st date, in that 1st conversation, if she's laughing, if you're asking her good questions, funny questions, Or if you're talking about topics that you're both enjoying and making you both laugh, then she's gonna wanna see you again. She's gonna wanna she's gonna say yes to that 1st date, or she's gonna want that 2nd date if you're on a 1st date. Or she's gonna just be that really, That woman at the bar who's just, she just met you. You're 5, 10, 15 minutes in. You're making her laugh. You should say you're laughing together. You're laughing together. It's not about and today's episode is not How to be funny and witty, although that has value. We'll talk about that in other episodes, and I have. It's about how to have fun. And the nice thing about amping up the fun factor is you can absolutely do it. You don't have to be the funniest, wittiest guy in the world. You just need to understand some real simple tools for amping up the fun factor. So for today's episode, I'm gonna give you five simple strategies, 5 simple tools to have a lot more fun on your next date in your next conversation with a woman, especially if you've just met her. And I'm also staying tuned to the very end because at about the 25 minute mark, 20 about the 20, 22 minute mark, I'm gonna share with you my single favorite ever first date game. There's a game, kind of a bar bet. It's a fun little 3, 2, 3, 4 minute game you can play on a 1st date. And it's my single favorite, fun fun creator. Fun generator. It's my number 1. I just made that up. It's my number 1 fun generator to play on 1st dates. And it's a really fun simple game. I played it literally 200 times on a couple 100 dates. And anyway, today's about solving a big problem that you're probably struggling with. At least if you're listening to this pod, which is your 1st date might be kinda boring, you're not sure what to say, you're not sure what to talk about, She doesn't wanna see you again. Maybe you get stuck in the friend zone. Maybe a woman says, hey, it was nice meeting you, but I'm seeing somebody, Or I'm not really interested in dating right now. Or I don't wanna. I didn't feel that spark. That's all the code. That's all woman code for, Dude, just wasn't feeling the romance with you. I just don't wanna date you again. And bringing fun To a 1st date or a 1st conversation with a woman is such an important part of giving her the experience of bringing value to her life, making her smile, laughing with her, giving her a fun time, and bringing a good fun energy is enough to get a 2nd date. It's enough to make a woman wanna see you again. Here's a quick story. I was in Miami about, 12, 13 years ago, and I was really, at this point, getting really good at I was starting to get really good at first dates, and really good at that first 5 to 10 minutes after an approach. And I was at The Fontainebleau Hotel, the lobby at the Fontainebleau Hotel on a Saturday night, and I'd finally gotten in the zone. And for the first time in my approaching journey as a single dude trying to get good at approaching women, I saw the matrix. The matrix was 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.com/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. I thought I was supposed to walk up to women and be cool And say cool, witty, clever, pick up artist y things. And this night at the Fontainebleau Hotel, I was walking up to women, and I was just being silly. I was having fun. I was teasing and joking. I was asking them silly questions, and I got 3 phone numbers in about 45 minutes. And one of them was this really beautiful woman named Brie, and I just remember her name. I remember how pretty she is and how classy and stylish. And I just remember her saying as she gave me her number, we talked for 10 minutes in the lobby bar of the Fontainebleau. She gave me her number and said, hey. Let's meet up. Text me. You're a lot of fun. You are a lot of fun. And that was a real moment for me when I realized, okay, Connell. Stop trying to find the perfect thing to say. Stop trying to be cool and show off. Instead, bring the fun. So let's do it. I'm gonna give you right now my top five favorite Fun factors. Way ways to amp up the fun factor. Here we go. Especially on 1st dates, but also in that first approach. Strategy strategy number 1 is to talk about fun topics. Focus on fun topics. This one is the easiest one. Simply monitor the conversation you're having with her and ask yourself, is this topic fun or is it not fun? So that's very simple. You don't need to come up with amazing shtick all the time. You can just keep topics, Keep the topics on things that are fun and light and more emotion based as opposed to information and logic based. So here's a story. Here's a quick story from a first date of mine. To illustrate this, I was on a 1st date once, and it was actually right after the pandemic ended because she and I were talking about how we spent the pandemic. And I remember she spent about 2 or 3 minutes getting negative about her pandemic experience. She was a graduate student in psychology. And she was saying how, oh, my grade I hated the pandemic. I took this online course for grad school, and I hated it, and she was just going down this rabbit hole of negativity. And in my mind, I'm thinking, not a fun topic. She hates grad school. She hated this Zoom course. Change the subject. And so I interrupted as politely as I could, but also I felt like I needed to take charge. I said, hey. Let's get back to that in a second, but do me a favor. Tell what were you saying earlier about those 2 cats you were babysitting? What was that story? Because that sounded really funny. You said the cats got into, like, a, they got into a funny fight or did they what were they doing again? And as soon as I changed the topic from her grad school hell to these 2 kitties that she mentioned earlier, her face lit up, and she smiled and said, oh, yeah. So I housed these 2 cats, and she told me this funny story. And the vibe of the date improved by 50% instantly. It became fun, and all we did was change the topic from why she hates grad school to why kitties are cute. So it can be as simple as noticing the topic and switching to something more fun. Here are some bad topics to avoid. Politics. Talking about people besides you and her who aren't important, who aren't really important to you or her. So it's totally fine if you And she talk about your parents, people you're closest to, family members, best friend. But you don't want to go down some long conversational rabbit hole about, I don't know, some guy you work with and tell a 5 minute story that's not really relevant to you or her. Or maybe she goes off on a 5 minute rant or story about What a jerk her boss is, and talks about all the problems she's having at work and her boss. Now you can empathize with that, but it's not a fun topic. So you wanna take responsibility for the date and make it a bit more fun. Make it a bit more fun. Other topics to avoid would be, you know, negativity, bad news in bad Bad news happening in the world. There's some awful news happening in the world. You don't wanna dwell on that or even mention it if you can. And those are some bad topics. Basically, anything that's logical, anything negative, and anything that veers too far away from you and her. The best topics to talk about are her, are you. I should say that we start with topics that are that matter to her and you. So if you might look at her profile if it's a first date, from the dating apps. You might look at her profile and say, okay, she's really into skiing. That's a fun topic. She's gonna wanna talk about that. She went on a wine tour of Napa. Okay. I wanna ask her about her trip and ask her what was the most enjoyable part of that trip. So travel's a great topic. Anything she puts on her online dating profile is a great topic. Her career is a good topic as long as you talk about it the right way. In other words, don't get bogged down in just facts and figures. Oh, really? So what year did you become an attorney? How long have you been practicing as an attorney? What, you know, what kind of law did you study in college? Those are okay questions to get information. But if you're gonna talk about her job, then talk about it through a more emotional lens. Emotion is the gateway to romance, whereas logic and information is quite the opposite of romance. And so you could say, oh, what do you love most about your job? What do you love most about being a lawyer? What lights you up? I love asking that question. What lights you up about your job. Other topics, great topics, music, food, people in general, women in particular, love talking about Fine dining, favorite foods. I had a 1st date once where we talked about coffee, different coffee, and we also talked about bagels.I had a bagel lover, And I had a date once where we just talked about coffee and bagels for 20 minutes. Now that might not seem like a sexy, hot, fun first date topic, but there's something that can feel really good about talking about things that are unimportant. It's a nice light topic. Because think about it. She's if it's a first date, Or if it's a Friday night after a long week, she just got finished having a very tough week in some ways. Right? She's got her work problems. She's got stress. She's got her boss maybe as being a jerk.Yeah. Everybody goes out on dates or they go out to socialize and have some drinks to get out of their logical information based mind, to get away from their problems, and to just talk about fun, dumb things. So feel free to talk about stupid shit. Stupid, dumb, fun shit. It could be bagels. It can be TV shows. I love asking my date about her favorite desert island TV shows. What show would she bring on a Dessa Allen with her? She could only watch that show over and over again. Food, Stupid stuff happening in culture. Talk about Taylor Swift and Travis, what's his name, If that's a light fun topic that lights her up or lights you up too. So this does not have to be super fancy. Have to be the perfect topic. Basically, use your common sense. Use common sense. Keep things light and fun, and that's gonna be giving her the gift of shifting her focus away from her problems, her bills, her job, her stress. And she's just with you talking about bagels and Taylor Swift and each other and getting to know you and her sharing her, That's gonna be a fun date. So the 1st and easiest thing you can do is switch to fun topics. One last example of this happening. My client, Trevor. I write about this in my book, in the chapter all about how to flirt. But my client, Trevor, was once on a date, And, his 1st date was with a beautiful, beautiful woman, a chef. Beautiful, gorgeous, successful Brunette chef in New York City. A totally amazing catch. And he'd been in the friend zone with a lot of women until we started working together. And this woman, her name is Becca, she was telling a story that frankly was kind of a boring story. It was something to do with shopping, and she was buying makeup and shoes. He was listening. He was trying to listen, but it was kind of a boring story. And he interrupted her and said, hey. I actually, we can get back to your story in a second, but you're never gonna guess what happened to me today. And he told this fun story about being on the subway and something weird and crazy happened. Now I'm not saying you should cut a woman off and interrupt her, but if you do notice the conversation is in a boring place, interrupt it, make it fun just by switching to a more fun topic. She'll appreciate it. 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 1 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. Getting dating sucks, but today you transform your confidence and find your dream girl. This is an example of you leading the date into a good place. So tip number 1 is talk about fun topics. Tip number 2 is play some fun games. Play some fun games. I love playing games on dates. 2 per date is a good amount. Any more than that, It can get a little bit gimmicky, but I love doing staring contests, thumb wrestling, 2 truths and a lie. Come to the date, prepare if it's a date or just be ready if it's a conversation. Be ready to say something like, oh, hey. You know what? Let's play 2 truths and a lie. Ready? And then you have 3 things ready to say. One of them's a lie. She gets to guess what it is. A game is fun. People love to play games. We're all wired to enjoy playing games.Staring contests, 2 truths and a lie. I like to play a game called The first time where I say, okay, I have an idea. Let's play a game. It's called the first time. We're gonna take turns talking about the 1st time we did something in our life. We'll just ask each other questions. So you might ask her, okay, when was the first time you traveled by yourself? And then she'll ask you a question for the first time. And you ask her another, what's the 1st time you went to a rock concert? What was your 1st concert? Basically, it's asking each other about firsts in life.
And a cool thing about this game is it's fun. You're getting to know each other. And if you want, you can dial up the flirting. Make the topic that you're asking about a bit more risque. You know, you could say, hey, who's the 1st kiss you ever had? How old were you when you had your 1st kiss? Or when was the first time you got drunk? And it can get a little bit risque from there. You could talk about the first, You know, if it's being dialed up, you can then start talking about your 1st time being intimate. 1st time having sex. Now be careful with that because some women might have a bad first time having sex story. So read the room, make sure that she's enjoying that topic. But you can lead up you can kinda dial up the sparks factor by talking about by asking first time questions that are a bit more Spicy as you go along. And my very favorite first date game, I'm gonna save to the very end of the pod about 5 or 6 minutes from now. So, I'm gonna give you my very favorite first date game to play. It's my favorite one and you'll see why in a couple minutes. Okay. 3rd tip for more fun interactions with women, fun dates, is choose a fun activity if you're on a first date. You don't always have to just get drinks or/or avoid having dinner for a 1st date. Avoid dinner. It can get pricey. You're sitting across from a table. Usually, you're sitting across from each other at a table rather than right next to each other. So instead, have a fun activity for a 1st date. Bowling, ping pong, pool, game a game, a game night challenge. Jenga is a fun first date. Go to a bar that has board games and play a game. Play a game of Jenga or whatever board game you're into. You could do Actually, one of the best activity dates I ever had. You can get really creative with this. Once during a New York City heat wave in August. I had a 2nd date with a girl I was very into, and we snuck into a hotel pool. It was kind of a fun devious thing to do. We broke the rules. I don't think we broke any laws, but we broke the rule. We pretended to be hotel clients. We got into the pool, and there was a swim up bar at the pool, had some drinks, and it felt like we were doing something bad. So it was a first and a 2nd date swim date. That was kind of a fun devious date. Karaoke is a great fun first date. So, yeah, have an activity For, do do an activity for your 1st date or maybe 2nd date. That's a way to amp up the fun factor. Okay. That was number 4. Number 5 is oh, sorry. That was number 3. I lost count. That was number 3. My 4th Fun factor tip is to have fun on dates and ask fun questions. Ask fun questions. This is so easy. Takes a little preparation. You don't have to, improvise it. You can come armed with 3, 4, 5 good questions in your back pocket, so to speak, to ask. And because you're gonna ask you're gonna ask some very normal get to know you questions, So that's fine. If you do want to ask, get to know your questions like, who are you closer to or or tell me about your parents, how many brothers and sisters you have? Where did you grow up? Those kinds of questions are totally fine and normal to ask on a first date. But to amp up the fun factor, you can ask some more fun questions. You can ask yourself questions. The game would you rather, if you Google would you rather Based on whatever the topic is you're talking about, or maybe just totally randomly. I remember I was on a date once where she was a big Harry Potter fan. So I said, okay, would you rather. I think I asked her though. I think I asked her, F Mary I said, okay. F Mary Dragon. I don't remember. So you could ask her, like, if Mary killed questions. You can ask yourself questions. You know? Would you rather, would you rather have the ability to fly or the ability of super speed? A Would you rather questions are great. There's a whole list of good first date questions in my book, Dating Sucks But You Don't. Feel free One of my favorites was always, okay. If you could have anybody play you, any actress, any actor play you in your life story, who would you choose? I like that question. I like asking when this is a this is, moving away from fun and potentially more into deep, but it can also be fun. As I like to ask, What was the best day of your life? What was the best day of your life? And that'll keep things positive and hopefully fun. That's a fairly deep question, but it's a positive one. Right. I love that question. So ask good fun questions. Google, Read the 1st date chapter of my book. Google some would you rather questions, and you could have 5 or 6 of them at the ready. And in the middle of the day, you can say, hey, I have some fun questions I wanna ask you. These are a little bit out there. Are you game? And then you hit her with some fun questions. By the way, they don't always have to be super clever. They can just be fun questions like, if you could, You know, if you could have dinner with any famous person, who would you have dinner with? If you could, you know, the desert island question I asked earlier. It can be as simple as that. You know, what's your favorite TV show? Your favorite movie? Who is your 1st concert? That's a good one. That's a good one. I like asking what's a story, what's a story from college that you oh, hold on. My iTunes music just started playing randomly. Oh, man. I hate Apple Music. Okay. You could ask about, you know, What's the what's what's the one story from college that you've never told your parents about? So as the date goes on, as the questions go on, you can sort of escalate things, make them more personal, more playful, more risque. Anyway, Okay. Let's end with my single Favorite first date game. This is tip number 5, which is to play a first date game that's called 5 questions. I did not invent this.
I forget where this comes from. I got it from some dating guru 15, 20 years ago. But anyways, I called the 5 questions. It's basically a bar bet. It's a little it's a it's a it's a trick. It's a trick game but fun, very fun. And I've done this on the majority of first dates I've had, and it's called 5 questions. And here's how it works. Basically, what you're doing is you're telling her that you're gonna play a game called 5 questions And all she has to do is get all 5 questions wrong. If she gets any of the questions right, she loses the game. And a great way to frame this is you might say this after the 1st drink, And it's time to order a 2nd drink, and you're thinking, hey, you know what? I have an idea. Do you wanna play a little game for a drink? It's a little bet. So right there , right there, upping the stakes, challenging her to a fun little wager for a free drink, the loser buys the drink. That is fun because you're amplifying the stakes. You're saying, hey, let's make this, let's make this mean something a little bit more. So, it's called 5 questions.
I'll take you through it. I'll do it right now. I'll basically do it as if I was on a date, and then I'll kinda role play both parts here. The great thing about this being a podcast is you can go back and listen to it and practice. So here's how it goes. So you're on the date and it basically goes like this. Hey. I have an idea. Let's play a game. It's called 5 questions. It's a game where I'm gonna ask you 5 very simple, straightforward questions. And for you to win the game, all you have to do is get all 5 questions wrong. Are you up for it? If you get any question right, you lose, and you owe me a drink. Are you up for it? She'll always say yes because it's fun. You're basically saying, let's have some fun. And then here is how the game works. So you're going to ask her 3 very simple, clear, easy to get wrong questions. And then the 4th question is a trick question as you'll see in a second. And then there's also a chance to have another trick question for question number 5, if she doesn't fall for the 1st trick question. So let me demonstrate for you. Here we go. Okay, cool. Let's play. Here we go.
Remember, remember Amanda, get them all wrong. If you get any of them right, you lose. Okay? Alright. Here we go. Question number 1. And then the first 3 questions you just ask her something incredibly obvious and simple to get wrong. Doesn't really matter what they are. So the nice thing about this game is you can make up the first 3 questions.
So you might say, alright, question number 1. What is my first name? Could be as simple as that. And she'll say, your first name is Chester. And you can laugh and say, that is Correctly, incorrect. So far so good. So she got it wrong. Right? And so you wanna give her a little reward smile. Good job. Nice job. So far so good. And then you wanna go to the next question. And as you're asking the questions, you wanna ask the question kind of like in an official way. Like, okay, here we go. Next up. What the next question will be, and it'll be literally anything. What is the name of the president of the United States? A super easy question, and she'll say something wrong.
Right? Robert De Niro. Whatever she says, whatever she says, it's gonna be funny. I love this game because it's it's it's it's you're setting up a fun payoff shortly, but it's also just a blast To have her say the wrong name. Robert De Niro. And you say, ah, that is wrong. Good job. You're crushing it. You're totally crushing it.
You're nailing this game. Now the next one. Now while you're doing this, you wanna keep count, And you wanna get to 3 simple questions asked and answered so that but you don't say the number as you go along Necessarily. You kinda wanna pretend like you're losing count. So the next one, you're asking question number 3 and you say The next one, whatever it is. What app did you and I meet on? Let's say you met on Hinge. What app did you and I meet on? And she'll say some incorrect answers. You know, we met on Grindr.
If she's funny, she'll say something like that. So you'll be you'll you'll both be laughing about her 3rd incorrect answers. And then you'll say, ah, nice job. Nice job. I accept your answer. It's right. It's wrong because it's right It's right because it's wrong. And then here's the secret.
Here's the move. Okay? You pause. You change your tone of voice from a question asking a guy to sincerely asking a sincere question, and you say to her, wait. How many was that? How many questions was that so far? And then she'll very likely say, oh, that was that was 3. So she'll give you the truthful correct answer, but that's the trick question. And then you say, you lose. Nice try. Sorry. You lost. So I'll do it again. Remember, so the way you ask the first 3 questions is, who is the president of the United States? What app did you and I meet on? What is my first name? Then you get to that next one, numb number before number 4, You say, wait, how many how many how many questions was that? You ask in a genuine sounding way, and she'll very likely say to you, oh, that was 3. And then you go, gotcha. I win. Gotcha. On the 4th and 9 out of 10 times, you'll win the game on that trick question. And that'll be great.
It'll be funny. She'll be mad, but in a good way. She'll be she'll be she'll she'll feel like she got got, and you can trash talk. Please do. I encourage you. Say, oh, gosh. You're terrible at this. Man, that was easy.
I hope you brought a lot of cash because I like really pricey drinks. What are you gonna get me? So you can, like, kinda lean into the trash talking, which is really funny. So that's how you win at question number 4. Now there's one other element to the game here that's possible. So you gotta stay on your toes. It's possible, unlikely, but possible that she'll have her guard up. And so that when you ask that trick question, How many was that? Question. She'll have her guard up and she might say, oh, that was 27 questions.
If that happens, don't freak out. In fact, it's actually an opportunity to win the game. You basically get 2 bites of the apple. 1st bite, I just explained. Here's the 2nd bite to win the game. If she's on to you and says, oh, that was 29 guesses or 29 questions, Then you pretend that she lost. I'm sorry. That you lost and she won.
You say, oh, damn it. I thought I had you. Shoot. You got me. I thought I was gonna get you. Man. You're too smart for me. Say something like, I thought I had you.
I thought I was gonna win. You're just too smart for me. Oh, shoot. I yeah. I usually think people usually crumble. Alright. I know when I'm beaten. So you play it up a little bit.
You play it up that she's the winner. You give her a false sense of security that she won the game. Right? And give her, you know, stroke her ego a little bit too. Yeah. You're too quick for me. I thought I had you. And then you say this very conversationally, very casually. You say, have you played this before? Now that secretly is question number 5 because that is the 5th question you've asked, But her guard will be down and she'll say, no.
No. I never played before. And then you say, ah, I got you on the 5th. You lose. And I'm telling you, dear listener, when you get that 5th question and she thinks she won but she lost, her brain melts. It's so funny. You get a free drink. She's gonna pretend like she's upset, but she's not.
She's having a blast because you're challenging her, you're teasing, you're joking, and you're having fun together. By the way so and that's so that's 5 questions. I played this 100 plus times, Never lost. I've only lost this game once to 1 person. I wasn't on a date. But so practice this game. Get good at it. Maybe do it To do it with family members and friends.
It's a fun little thing you can do with anybody. It's not just a first date game. But there's just something about it. It's just silly. It gives you both a chance to laugh and trash talk, then she gets to buy you a drink if she loses, which I'm sure she will. It's also, I think , a fun psychological test. And I've actually said this to my date after the game is over. I said, "Let's say she lost on the second one.
The first trick question, if she loses on that one, it's because she's a helpful, giving person. She's trying to help the game by telling me how many questions there were. And so I'll say, well, you or this game's a psychological examination. If you miss the first question, it's because you're Helpful and sincere in trying to give back. If you miss the 2nd question, the 5th one, it's because you have a huge ego. So if she misses on the last one, you can say, apparently, you have a giant ego. You just thought you'd won the game and you didn't. Anyway, it's fun trash talking.
It's just silly. And, try out the 5 questions. Please rewind. Go back and listen to this episode again. Listen to how I talk. How you set the game up is really important. Or it's not really important, but it's fairly important to frame it as a really fun game. Just get all 5 wrong.
If you get any question right, you lose. And then you'll enjoy that. So those are the 5, My 5, fun escalators. Call them the fun escalators. How to escalate, amp up the fun on first dates. Number 1, talk about fun topics. Number 2, play fun games. Number 3, do fun activities if it's a first date. Number 4, ask fun questions. And number 5, play the 5 questions, the game I just did. That's my favorite game ever. My favorite first date game ever, and I think you're gonna have a blast with it. Alright. Thank you so much for listening. And, yeah. Remember, bottom line.
Hey, Cindy Lauper was right. Girls, they wanna have fun. She also said, bebop. She bop, she bop. So she was 2 for 2. Alright. Remember, your beautiful, cool future girlfriend, she's out there. She already likes you. She just has to meet the real you. See you next time.Thank you for listening to the dating transformation podcast. For lots of free tips, videos, and other goodies, go to dating transformation.com. See you next time.
Produced 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
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