10 Things You Shouldn’t Say On A First Date

Co-written by Stephanie Georgopulos.

“So, what’s your number? Five? Ten? I’m just curious, no judgment here! But like, you’re really hot, so I bet it’s high. Is it over twenty? I’ll tell you mine if you tell me yours. Wait, really? I don’t believe you… there’s no way you’ve only slept with seven people. I mean, really, I’m not gonna tell you mine if you’re just going to lie straight to my face. Seven… yeah. Okay.”

“Haha no but seriously I’m wasted. I feel like alcohol is super good for that. I mean like whenever I go out I always take a few shots beforehand, it really helps me. I know we’ve only had one drink but I’m flyin’ high! HAHA. I’m having such a good time already. Do you believe in the concept of soulmates? Want to take shots?”

“You seem like a pretty upbeat girl, yeah? I was wondering, uh… ever think about what’ll happen when you die? We’re all gonna die someday, it’s not weird to think about. I mean — death is everywhere. Do you think it’s weird to think about? Ever wonder who would skip your funeral?”

“Oh — you need to go? Sure you don’t want to like, go back to my apartment and take off our clothes together? Just kidding! Haha. Got you. I was totally just kidding. All my friends know I joke around a lot. You’ll find that I joke around a lot. I’m a really funny guy once you get to know me.”

“Oh, I haven’t had champagne since I was with my ex, who totally screwed me over by the way. What a mistake I made with her! Hah! I mean, not that you asked, but let me tell you how much of a whore this girl was. You know what — nevermind. Forget I said anything. It’s just that… let’s just say that she went around the block a few times while she was with me. I’m not trying to say anything about her right now. Who likes a person who talks about their ex on a first date? F-ck her though, seriously.”

“Are your parents divorced? I’m asking because studies show that a child of divorce is likely to get divorced themselves, eventually, and my parents are divorced so if we’re two for two here… we’re kind of screwed, right? Like, this date would be pointless. Right?”

“You work on Prince? There’s this neat little Italian place a few blocks down, we’re totally eating there on our second date. I can meet you at your job? Oh… oh, wow… you do want to go on a second date with me, don’t you? I uh… I think, I thought we were having a great time so I just kind of assumed that we’d do this again, a few days from now if that works for you? If that fits in your schedule?”

[~5 second pause in conversation] “Do you think this is an awkward silence? Hah. I think this is really awkward. Sorry, I’m just an awkward person sometimes. It just seems like we have nothing to say to each other. Ummm. Wow this is really awkward, isn’t it?”

“I just have to warn you ahead of time that I’m always, always working. I work fourteen hours a day, seven days a week. But babe, it’s like my father and my father’s father and my father’s father’s father worked those hours, too. You can’t just become a 53%er overnight. It takes generations of manual labor and blood. Lots of blood. No handouts for anyone, am I right? You brought your wallet, right? We’re going dutch.”

“Well. What should we talk about?” TC mark

image – Beraldo Leal


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  • Mashka

    “Do you think this is an awkward silence? Hah. I think this is really
    awkward. Sorry, I’m just an awkward person sometimes. It just seems like
    we have nothing to say to each other. Ummm. Wow this is really awkward,
    isn’t it?”  

    That has legitimately happened to me. Not even on a date. When I was out with a friend this guy I had been seeing met up with us and this is what he said to me. Yes, thanks, NOW it’s awkward now that you said that. Otherwise it wouldn’t have been. He later asked me if we “talked about him the entire way home”. Yikes.

  • Anonymous

    Oh my fucking god this was so funny. I just went on a date last week and I loved reading and agreeing with all your not-so-subtle neurosis:

    Past sexual history, alcoholism/soul mates, inappropriate subjects, sexual intimacy, ex-lovers, long-term compatibility, future dates, feeling comfortable, etc.


  • http://twitter.com/kyleangeletti Kyle Angeletti

    Hilarious. Glad I caught this one. 

    Guilty of pulling the fourth one from the bottom. 

  • http://twitter.com/nawasaka Becky To

    “Do you believe in the concept of soulmates? Want to take shots?”

    Bam, gotta try that line this weekend when I’m out and about :)

  • Mashka

    “we would have really good looking children” is another one.

    I mean it’s funny if it’s with someone you know but on a first date, hellz no I don’t care how babely you are.

  • http://www.facebook.com/profile.php?id=9383035 Scott Muska

    Dude. This is great.

  • http://alisoniven.com Alison

    I was just about to text this guy I met this past weekend a “sorry I’m awkward” message… until I read this!

    • gueston

      I just did that today :( but dude txt me bk to hang out :)

  • http://www.facebook.com/profile.php?id=1363230138 Michael Koh

    Died laughing… I could relate. 

    Is this a compilation of your first date experiences? JK guys! Love you!

  • adsaqw aqw

    Haha hilarious

  • sequinsbythesea


    also “Wanna hear something awkward? My dad died last week.”

    and “Can I ask you a personal question? Are you familiar with Missoni for Target”

  • Anonymous
  • YOKO


  • Sophia

    I HATE PEOPLE WHO POINT OUT AWKWARD SILENCES. thanks for it awkward, buddy.

  • Tyrone

    ahhhh the second one  is me every friday.

  • Anonymous
  • Janelle

    Laughed out loud reading the awkward silence paragraph.

  • Steph

    Past the pain, I now see a few reasons why it didn’t work out with this guy I dated. He asked me these two things when we first went out: What is my dream wedding, and am I high maintenance? Looks like it’s true sometimes the first questions asked can tell a lot.

  • Anonymous
  • http://www.facebook.com/profile.php?id=1272952278 Paige Stocking

    “I’ve been told I have good birthing hips…”

  • http://gapersblock.com/ac/2011/10/20/chicago-dating-2011-the-first-date/ Niki

    Love this! Totally just wrote something similar for Gapers Block about the do’s and don’t of online dating first dates:http://gapersblock.com/ac/2011/10/20/chicago-dating-2011-the-first-date/. My biggest ugg moment was confusing date’s stories. I need to start keeping cheat sheets.

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