The Worst Things to Do on a First Date


Everything that’s going on in my email box right now.

You guys keep emailing me and asking what’s the best thing to do on the first date. And I appreciate it, I really do. It’s nice to wake up in the morning and see so many messages in the It’s Not a Match in-box, especially when all that’s in my personal one are two emails from my Mom, and a message from a girl named Tanya promising XXX SUPER HOT NUDE PICS JUST FOR YOU HONEY, TOTALLY REAL!! which I’m starting to think is a hoax. I mean, if they really were just for me, why do there seem to be so many people CC’d? And if they’re real, why does she looks like someone attached two Goodyear blimps to the chest of an underfed Russian woman? So many questions, so few answers. If only Tanya would ever write back!

Seriously, as much as I like hearing from the readers, my response to the first date question is always the same: Get Drunk. Don’t get messy, sassy, or stupid–just get a nice, respectable Dean-Martin-Christmas-Special kinda drunk. No shots, no drinks with the word “sex,” “slide,” or “blowjob” in them. Just a couple of cocktails, wines, beers, or Zimas. (Zima is Tanya’s favorite. Probably.) Do you need alcohol to have a good time? No. But you might need it to have a good time with someone you’ve never met who could very well be awful. I mean, come on. If someone walked up to you and said “Hey, see that chick standing in the corner? You’ve gotta talk to her this minute. I’ll tell you her name and her job and what she likes to do on the weekend, but you’re probably gonna forget. So GO.” Are you gonna slug back a bourbon first, or just go at it stone-cold sober? You’re taking the drink. You’re looking at the guy like he’s a lunatic, and then you’re taking the drink. Because drinking makes meeting someone easier. However, the following date ideas do not…

"It was really nice meeting you, but now I have to barf!"

“It was really nice meeting you, but now I have to barf!”

GETTING COFFEE: What, the evening doesn’t have you jittery enough, you wanna throw some caffeine into the equation to see what happens? Why don’t you just meet your date on a roller coaster, or, say, the inside of a volcano? I have never, I repeat NEVER had a good first date that involved only coffee. You can’t meet at Starbucks, because that’s just depressing, so instead you meet at an Independent Coffee Purveyor, which is either going to be dank and dirty or filled with strollers. I’m not sure which is worse for romance, but neither is good. And then what happens if the date is going well, you get a…second cup of coffee? Good grief. Dating is the anti-Glengarry Glen Ross: Coffee is Not for Closers.

PLAYING POOL: Why not invite your date to change your carburetor, or perhaps perfectly shave a man’s Adam’s apple? I mean, how far exactly do you want to take your date out of her comfort zone? Women often feel insecure about their pool playing ability, thinking it’s something men are either great at or care about tremendously. Neither could be further from the truth. It takes me 45 minutes to clear a pool table, and that’s with me manually dropping balls in the pockets when no one’s looking. But why pick an activity that is very possibly going to make your date nervous? There are plenty of women who love and are great at pool, but they’re in the minority, so don’t risk making the night uncomfortable. And if you think the thing where you teach them how to line up a shot is going to be cute and datey, you’re wrong. It’s gonna be weird and gropey. Put down the sticks and order a DRINK.

Also an option.

Also an option.

PLAYING DARTS: Sure the date is going badly now, but what if we introduce small, pointy knives into the equation? “Ooops! She hit me in the eye! I guess at least I don’t have pay for drinks!” I actually think darts is a pretty good date activity, because no one’s particularly good at it, which evens the playing field. Unless you’re one of those burly darts aficionados who’s known as “The Hammer” or “Bullseye Barney,” but something tells me snarky dating blogs really isn’t your thing, so I’m not speaking to you. If you’re gonna play a game, darts is a good choice, because it doesn’t monopolize the conversation too much, but still, it’s distracting. And really, any activity that increases the likelihood of a punctured lung is never a great date game plan.

GOING TO A MOVIE: Is there a way we can get to know each other less? What if we just watched DVDs separately at home? Or, how about this: at exactly 6:15 you take a two-hour long nap at your house, I’ll take one at my house, and then we reconvene afterwards to see how it went? Sound good? GOOD!

GOING OUT FOR DINNER: It guarantees the date will be long, expensive, and possibly result in gas. BINGO! I believe we have BINGO!

WALKING OUR DOGS TOGETHER: No good first date involves feces, human or otherwise. However, tune in next week for why it plays an integral role in date #3! (I’m kidding. As far as you know.)

This entry was posted in Advice, Internet Dating is Weird. Bookmark the permalink.

19 Responses to The Worst Things to Do on a First Date

  1. dsantos85 says:

    well that pretty much rules out any ideas i’ve ever had for a first date :/

    any suggestions to where IS a good place to go on a first date?

  2. Paula says:

    Thanks for putting the absolutely HORRIBLE Starbucks “date” first. The most unromantic thing ever. Also bad? Going to a swapmeet and watching a guy haggle for undershirts. My god. The swapmeet idea itself isn’t bad because it involves walking and talking as opposed to sitting and caffeinating, but the undershirts? Just no.

    • betsy says:

      Brings back memories of the worst date I ever went on, where to kill time before the movie we went to a Starbucks and I learned all about how much smarter he was then everyone else in his accounting class.

  3. sexyawkward says:

    How about a combination coffee and pool? Because that’s what my first match date was like. -_-

  4. betsy says:

    This makes me wonder how all those Match-endorsed Stir events go, like the ones where you have to make pasta or dance (as opposed the ones where it’s just 50 people at a bar).

    • The Most Semi-Interesting Man in the World says:

      I attended exactly one of Match’s crappy, one horse popsicle stand, hood-rat thump hump bar stir events. 50 people sat around looking at each other and the bar feigned ignorance over the happy hour discount Match advertised. If there are some outgoing people who work to make introductions it can work, but most people (especially guys) at these are not exactly forward from what I’ve witnessed, but then that worked to my advantage. Unfortunately for the women, most of the men sat there waiting for a sign from the universe to introduce themselves so most women at the one in Houston I attended left disgruntled to put it mildly. Bottom line, find something that is organized and has a requirement for interaction like cooking, etc.

  5. Sapphire says:

    Hey, gotta defend the coffee date! There enough funky interesting coffee places that nobody cares if it takes you an hour to drink your joe. So easy out if it’s a loser, easy transition if it’s going well. And meeting mid-afternoon is definitely possible. So don’t diss the coffee date!

    Btw, b, I found ANOTHER 419 scam artist. Doesn’t anyone think you use google image? This one I busted after one e-mail and called him out before I notified. Match…

  6. Andrea K says:

    I never understood the pool thing. Why pool? Why not just challenge me to a game of basketball, and then we can really see how uncoordinated I am.

  7. Pingback: Do Coffee Dates Work? « Smooth ReEntry

  8. jenyphero says:

    I beg to differ on the pool thing. I can’t play for jack, but I like to slip the balls in the pocket when he’s not looking. Plus, if he doesn’t call me on it, it lets me know he’s a keeper!

  9. Natalie says:

    B, you’re the face of Salesforce!

  10. Wilson says:

    In NYC, there are tons of chill coffee shops and cafes. They’re a much better place to have an actual conversation, as opposed to one of the many pretentious lounges and wine bars in the city.

    Furthermore, I don’t drink. Thus, you’d never find me in a bar.

    The author’s mindset is totally flawed. A first “date” isn’t about romance nor about “closing.” It’s simply an initial meeting.

    If closing is your main concern, then visit a hooker.

  11. Larry S says:

    I agree with @Wilson. Coming from Vancouver (Canada), there is an abundance of awesome coffee shops. In coffee shops, you have a better chance of understanding the person you are trying to date, gaining the ability to know her/him better. As much as I love drinking, bars are loud, noisy, and you are in a state where you are intoxicated, the decisions and choices you make will in turn be clouded. I also want to add that the best relationships I had all started as a first date in a coffee shop. Oh, and you don’t have to order coffee if you can’t handle it, most good coffee shops sell a bunch of other things too, like tea, or other non-caffinated beverages. If your coffee shop date turns out to be boring, that just means that either you or your date aren’t interesting enough to make it work. Unless my goal is getting laid by the end of the night, I never have a first date in a bar. (pubs and restaurants that serve alcohol are different)

  12. Pingback: Great Date Ideas If You Absolutely, Positively Refuse to Drink | It's Not a

  13. AbrahamLincoln says:

    I agree on the darts too. I had a date once that while good lasted for a very long time because for the life of us we couldn’t close out the fucking bullseye. Oh you’re tired? Well tough luck because this date ain’t over till one of us hits that silver dollar sized target from 8 feet at least two to three times.

  14. 30's Dater says:

    +1 for avoiding coffee dates at all costs. An environment that lackluster requires not only you but your date to perform at such a high level to generate enough interest for date #2 that it turns a hard situation into a nearly impossible one. Drinks make the convo flow better, but my issue with that is that my hands begin to wander after the 5th drink…lol

  15. Beth says:

    I do not suggest the Sports Bar. My “date” would ask me a question and as I started to answer his eyes would be gazing up at the big screen TV off to the side. After and excited “Oh yeah!”, “Sweet”, “That’s it!”, or some such he would return his attention to me. These were just clips from games and not even a real game. Of course, if your date posted she is into sports and drinking, then go for it.

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