12 Tips for Making Every First Date Great


After the recent Sir Hugo saga (as well as the ever-so-slightly unhappy situation with Sean O'Sean)--not to mention some other Internet first-dates that were a bit too mediocre to mention--I decided it would be wise to take a break from the Internet singles world. Though I seem to be more comfortable than the average person when it comes to making small talk with strangers, even I have been feeling a little burned. Time to get off the online personals merry-go-round! I thought.

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But when I mentioned my malaise to OkCupid Matchmaker Extraordinaire Meghan Beresford, she had some words of wisdom about how I (and you) can make every first date a positive experience--even if it doesn't lead to TRUE WUB.

Here's what she had to say:

#1) DO view every first date as a mini-adventure. At best, you'll meet someone you want to see again. At worst, you'll meet someone you find unattractive or strange, and you'll get to excuse yourself after a short period of time--in which case you'll have a story for brunch with your friends this weekend.*

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#2) DO expect to be surprised. He may be less (or more) attractive than his pictures suggest, or more shy or geeky than he seemed during chats with you. Why? Because he posted his most flattering shots and busted out his wittiest quips to impress you. You probably did the same. The transition from online to real-life can be jarring, but if you head into it without pre-set expectations, you won't feel the jolt so much.

#3) DON'T think of dates in terms of success and failure. A bad first date doesn't mean you're unloveable or that you attract losers and weirdos. It means that there is a vast sea of people out there who aren't right for you, and you're going to bump into a bunch of them before you find the person who is.

#4) DON'T "fall in love" before you meet. Avoid too much time emailing, texting or talking to him before you meet. Doing that can set the stage for huge disappointment and discomfort if you show up and realize, for instance, he's about 100 pounds heavier than he'd indicated--or that the two of you simply don't have any of that mysterious chemistry.

#5) DO consider the venue. Pick a low-pressure location where you'll be able to hear one another. If he's 'meh' on anything but casual drinks, don't take it personally: some guys say that doing activities on first dates feels too 'couple-y', while others can't think of anything better than meeting a strange chick for bowling and beers. Feel him out and decide together what would be fun and comfortable for both of you.

#6) DO be a good listener. People feel a stronger bond with those they've shared personal information with, compared to those who've talked their ear off. So empower yourself--and come off as more attractive--by listening more than talking. To get the person across the table from you going, ask SPECIFIC questions, rather than vague ones (or worse, those that require a yes or no answer). Aim for a series of easy-to-answer queries on a familiar topic. Location, for instance. Try: "What hood do you live in?" ... followed by "How long have you been there?" & "Isn't that awesome burger place down there?" & "Do you want to stay when your lease is up?" Those kinds of queries will cause more chatter than "So how do you like living in New York?"

#7) DO accentuate the positive. Complaining about your job to your friends is one thing--and perfectly fine (up to a point)--but it rarely comes off well when you're too negative during a first date. Make a great impression by waxing enthusiastic about upcoming events you're excited about, some awesome movie you just saw, or the great family (or goldfish) you have.

#8) DO have an escape plan. Rather than lying about how you have to be some where, and bolting, a smarter approach is to make REAL plans with friends for after your date. Mention those plans either before the date starts (possibly via text) or first thing when you show up; it's good manners and will make your eventual disappearance easier. At the same time, you should give the date at least an hour. Sometimes people need a little time to loosen up and hit their conversational stride. If the person is absolutely intolerable, stay for a drink's length (30 minutes or so) and then find a way to excuse yourself.

#9) DO offer to split the check. And if he takes you up on it, don't be offended. It doesn't necessarily mean he doesn't like you; it could just be that he doesn't want to come off as old-fashioned.

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I think all this advice is pretty right-on--although, as I've said before, I don't like splitting the check on the first date (or the second!). Call me old-fashioned and sexist all you want; those descriptions might be accurate. But if a guy isn't willing to buy me dinner or a drink, I think it's probably a sign he's not very generous in all sorts of ways. I will, however, offer to go Dutch if two factors are at play: (a) I think the guy doesn't make more money than I do, and (b) I think the date hasn't gone well. In a situation like that, splitting the check sends a subtle signal about my tepid reaction. And it also seems more fair.
Regarding the escape plan: That is a stupendous idea! Even if you LOVE the date, leaving when you are both wanting more is smart. Plus, your escape plan will enable you to control the good-bye, to some extent, so you're not left waving sayanora with your hat in hand.
Finally, I myself have one last piece of advice:
#10) DO look at every date as an opportunity to learn some new fact or piece of information--or just to see the world through a different lens. Maybe it's just living in NYC, but even when I'm not hot for a dude I meet, I almost always learn something really interesting from him. Sean O'Sean, for instance, told me that a big reason that The Beatles were so successful is because they took ideas that were universally appealing--Love is All You Need, I Want to Hold Your Hand, Happiness is a Warm Gun*--and boiled them down into catchy lyrical phrases. Last summer, I went out with another guy--a brilliant playwright whom we'll call Edward Albeestein--and we were sitting in Prospect Park, watching kids in the distance fly kite, when he said, "It's as if we're on the floor of a pond, looking up at the tadpoles swimming." It was such a beautiful simile that I've never forgotten it.
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Dating blogger Moxie wrote me on Twitter with two REALLY smart pieces of advice:
#11) DO offer to pay the tip if you're not comfy splitting the bill. If you are a sexist girl, like me, and you don't feel happy going Dutch, footing the tip is a way to contribute to the experience.
#12) DON'T GET TOO DRUNK WHATEVER YOU DO!!! I can't believe Meghan and I forgot to mention this! Thank goodness Moxie came to the rescue. Because seriously, getting wasted on a first date is never wise. If you're slurring your words by the time the dessert menus arrive, that might be a turn on for an alcoholic, but everyone else is going to see it as a BIG red flag. Just as bad--if not worse--you might end up doing something you regret (like, oh, I don't know, giving him a blow-job in the taxi home). Better be safe than sorry.
How to hold yourself back? Tell yourself ahead of time you will only have ONE drink if you're not eating, and TWO if you are. Seriously people: Call me a light-weight--I am one--but I had two huge glasses of wine on a date at the Pegu Club once, and by the time we stood up to go, I nearly toppled over into a table full of I-bankers at a nearby table. Not exactly my best moment. And though I thought the date had gone pretty well, the dude put me into a cab with a promise to call once he returned from a weekend business trip--but he never did.
Then there was the OTHER time I got seriously sloshed, and ending up crying to a random guy about a friend of mine who'd recently died ... not pretty.
Here's another trick: For every one serving of alcohol you have, try to get in 3-5 waters. (I'm not kidding.) Between waiting for your aqua glass to get re-filled and maxing out your bladder capacity, that will help slow you down.
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Anyway, lovelies--thoughts? Objections? Comments?
*That's a little joke.


PS: Commenters: I'm glad you're all with me, when it comes to pics of hot chicks!

As for my therapist: I-Heart: I'm kind of with you on the cynicism ... although I don't think my shrink would try to tell me I needed to stay if she didn't really believe it. But I question her judgement--and wonder if the therapy hasn't already done whatever it's gonna do. And Raye: I do question her efficacy. But she is trying to argue that I am pulling away from her because we're finally getting really close--and I'm scared of that--and my fear of getting closer to her mirrors my fear of getting close to someone in a relationship. Uh, mind f*ck, anyone? I feel like I'm in One Flew Over the Cuckoo's Nest sometimes. Oh well.


What do you think?