How To Ruin A First Date

I’ve been on a fair amount of first dates in my life, some ending well, others… ending. And like any human emotional endeavor, there is a certain amount of risk involved that you will reveal your inner sociopath far sooner than intended. Having made that particular mistake myself, the following is a list I’ve compiled of things I’ve learned the hard way not to do.

1. Be emotionally slutty. This is perhaps more often a female problem, although I have myself seen a man go on a 20-minute diatribe on his ex girlfriend’s habits before the appetizer arrived. In any case, don’t let a few glasses of wine and the overwhelming pressure bear down on your carbon-based soul until you become diamonds of terrifying emotional information. My personal poison of choice is the whole “I Want a Family” spiel. Many times now, I have been on a date and temporarily blacked out, coming to only when I’m halfway through a sentence about how “I want to be a writer because it will allow me time to be with my children. Children are very important to me, I’d like two ideally.” The man sits there, looking painfully polite, glancing at his watch, beads of sweat forming at his temple. It’s as though I’ve reached down and pulled out my ovaries, placed them on the table between us, then asked him about his day. No big deal, I’m just reminding you that I have a biological clock and it’s ticking. Generally, when you are just getting to know someone, playing it coy seems to be the better way to go. If, unlike me, you are capable of stomaching your innermost fears and personality tics for the evening–you’d be well advised to do so.

2. Talk too much. This is a specific kind of talking here, and one I am quite guilty of myself. You know how in movies, often at the end of the date, one of the partners will charmingly go off on a little tangent of the “Well, if you’re free tomorrow I’d love to see you, but I know you’re probably busy, but I’m busy, too, well, you let me know. I mean, if you want to, no big–” variety? Right. Well, invariably, the other person will cut them off mid-sentence in a romantic, sweeping kiss and they will embrace there on the sidewalk, stars twinkling above them, moon giving them that “You go, girl” look and the soft summer breeze handing the guy a condom. Yeah, that doesn’t happen in real life. You just stand there, rambling, getting progressively more awkward and uncomfortable until you cut yourself off with an “Umm, goodbye” and walk hastily in the other direction. Better to just keep quiet.

3. Get drunk. The temptation is obvious. You’re in for some rough human interaction, and there’s alcohol everywhere. Let’s lubricate this thing before we both realize how uninteresting the other person is. Unfortunately, there is a very precarious line between “a glass of wine giggly” and “six tequila shots sloppy,” and in the moment, it’s disastrously hard to see. One moment, you’re coquettishly rimming your martini glass with your finger, batting your eyelashes, and laughing at all the right jokes–then suddenly you’re crying on your floor and your roommate is stopping you from sending him a tenth text message apology of the night. We also have the unfortunate predicament of feeling like we come across as incredibly seductive when we just look like the oldest kid on the playground–a bit sad, out of place, and all our clothes are dirty. If possible, stick to a two-drink maximum.

4. See a movie. This has just got to be a matter of principle. If your first date consists of seeing a movie, even for part of it, it has already been ruined. Could you imagine saying to your partner, “I’ve only just met you, I know almost nothing about you, I would like to spend these magical first few moments with you in a dark room where we are not allowed to interact and are facing a screen in front of us”? It’s so…lazy…to think that anyone would want to miss out on these first few conversations where everything is so goddamned interesting for no reason. Who says to themselves, “That’s okay, I’ll let Matt Damon do the talking for me tonight”? You took this person out, at least pretend to be interested in them for a few hours.

5. Don’t offer to pay. This goes for both parties. I have known girls who proudly state that they don’t bring a wallet on first dates, and any man that would let them pay even a tiny bit is not one they would consider going out with again. For those girls, I hope the man accidentally left his at home and, on realizing how much of a gold-digging bitch she is, drives home without her and leaves her with the bill and trying to find a way home with no money. I always go into dates with a full intention of paying at least my share, and would never order things if I wasn’t prepared to pay for them myself. Usually, the man will insist on paying–and that’s fine. I get the gender roles, I appreciate their desire to be a gentleman, but I am honestly willing to pony up my share. There are so many girls that do the fake-out “reach for their wallet” move (their hands have never moved more slowly) as they pretend that they would ever consider putting a monetary value on the food they’ve just eaten. The man, of course, stops them mid-reach and they do that airy giggle of, “Oh! Well, if you insist!” I picture them all taking up Georgian accents circa 1870 and referring to their dates as “gentleman callers.” Quick tip, ladies: It’s nice, if you have the time, to take the man out for a gelato or a coffee as you walk after and insist on paying. It’s a little nothing, but it shows that  we do occasionally open our wallets and the credit card/woman going down ratio isn’t so prostitutionally high.

Don’t worry, though, if you make it through these five rules, you’ll still have a whole relationship to ruin. TC mark

image – Jon Sullivan

Chelsea Fagan

Chelsea Fagan founded the blog The Financial Diet. She is on Twitter.


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  • Jenna

    prostitutionally. kekeke.

  • Tom Smith

    I really liked the line about the overwhelming pressure forming diamonds of terrifying emotional information. Sweet metaphor.

    • jess

      i was going to comment the same.

    • El puto

      yes vn

    • meditationsONAsubway

      “the overwhelming pressure bear down on your carbon-based soul until you poop out diamonds of terrifying emotional information.”

      could've been a more visually descriptive metaphor, IMO


    Thank you for #5.

    I would also like to add #6: talk about heavy drug usage and/or offer ecstasy on the spot.

    •!/nvvmxac danne rassle

      if a girl opens up to me about drug usage on the first date i'll know she's tyte right there

      • Kia Etienne

        hell yeah, cause nothing says 'dis bitch be tyte' than her snorting a line with the money to be used for the tip.

  • Lim Yan Yun

    #6. talk about your pet.

    no, seriously.

    • Rose Meza

      Or worse, pull out pictures of said pet. One of my friends does this to deter people heheh

  • SousChefGerard

    If you switch out a Louisiana accent for the Georgian one, you will have my last date down perfect.

    BOOM! Nailed #1 without even noticing.

  • El puto

    Love number 5 and your style of writing in general.

  • Julian Tully Alexander

    All of these are dead on.

  • Andrew F.

    “I picture them all taking up Georgian accents circa 1870 and referring to their dates as “gentleman callers.””

    This is so great.

  • Carlos Ortiz

    If I had a dollar for every first date I've ruined I'd have 2 dollars, if I had a dollar for every good date I've had I wouldn't have any money.
    So I have a dollar for every good date I've had.
    Why do I always take them to the movies?
    Oh, that's right I'm lazy.

  • Sas Jam

    Thank you, Chelsea for at least setting up the rules on paying.
    I typically prefer to pay (I mean how else can I seem like I got it like that?). But NOTHING is worse than someone entitled just sitting there like “well, you know what to do”.
    Good article.

  • Comic Insult

    Admitting that you did a little Internet research on your date. That could be #6.

  • Steven Timberman

    You had me at “emotionally slutty”. A friend noticed that I always hold hands with any girl I'm casually seeing, and she accused me of “just giving away the importance of your hand”. We were both drunk at the time, of course.

  • lathompson

    !!!!!!!! awesome.

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