Dating has always been my greatest impediment to quitting drinking altogether. Even in my later years, as my body has begun to reject alcohol with a greater vengeance, I’m still quick to screech “let’s get drinks tonight!” at every opportunity. I like the familiar formula of a date in a bar, and I like that it’s casual and low-stress.
Maybe it’s Dryuary. Maybe you’re doing the Whole 30. Maybe you just don’t feel like drinking. Whatever the reason, there’s a lot of value in doing a sober date, even if you’re a drinker: You’ll probably spend less, you won’t wake up with a hangover, and you’ll be able to evaluate how you actually feel about a person. As one sober-ish friend, an advocate of the coffee date, put it: “If you need to have five drinks in order to have sex with someone, you don’t actually want to have sex with them.” And furthermore, should you make it to the bedroom after a sober date, you won’t take off your shirt to find that your ordinarily svelte physique has become a bloated barrel thanks to the six beers you nervously drank on your date. Should you, too, wish to avoid barrel bod, here’s how to execute a good fun sober date.
Pick an activity you’ve done before.
When planning a sober date, a whole world of exciting activities suddenly opens up before you, and you might feel pressure to pick something really memorable and out-of-the-box. Ignore that pressure. The Bachelor always sends couples skydiving so they can “get out of their comfort zones.” On real life dates, at least one of you should be in your comfort zone. I don’t want to “try something new” together—we’re both already trying something new by going out with a new person. I want to get to know you under circumstances where you feel at ease, not stressed. If you like to go skeet shooting on weekends, take me skeet shooting. If you’ve never shot a gun before? Let’s just have coffee.
Consider a museum.
One day in October I walked by the Museum of Pizza, a pop-up, pizza-themed museum in Brooklyn, and saw a line of about twenty couples waiting to pay $35 per person to go inside. The Museum of Pizza was the perfect date: Everybody loves pizza, at least conceptually (even lactose intolerants could see the artistry in the “cheese cave”), it could take anywhere from one two hours to pass through, and there was food. Art museums are ideal sober dates even if you hate museums on principle, because they’re often boring and usually quiet. You end up talking to each other the whole time anyway, but you can still stop and pretend to contemplate some art if the conversation hits a lull.
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Make sure whatever you plan has a start and a finish.
Museums also have a logical endpoint—either you see everything, or you get so tired you have to stop museuming. My nightmare sober date is a Christmas market: We meet there, we buy $8 hot chocolate, we immediately realize there’s not actually that much to do at a Christmas market if you’re not willing to drop $900 on tchotchkes, and then we must meander aimlessly, talking over screaming children, for the one or two hours it takes to constitute a date.
Make a plan and stick to it.
The easiest way to do endear yourself to a woman is to plan everything. Suggest a time and place to meet and then show up at that time and place, and you’re in. I might not care for fishing, for instance, but if a guy tells me that he’s going to take care of all the logistics—transportation to the fishing hole or whatever, meals, rods, boat—then I will meet him at 5 a.m. and fish merrily for hours. I don’t even want the responsibility of picking between two sober date options. I just want to be gently but decisively guided along a prescribed itinerary.
But don’t over-plan.
A lot of people mistake “sober date” with “jam-packed day of fun.” On one memorable first date, a boyfriend led me around Chicago on a demented eight-hour journey. We went to a Soviet propaganda exhibit, we got giant cupcakes, we sat outside and watched an orchestra orchestrate, and then we went out to dinner. Charmed as I was by the effort he’d put into planning our romantic death march, by the end of the date I felt exhausted and ill from the giant cupcake. Any one of those activities would have been a perfect date on its own, but doing all of them in one day was stressful. Afterwards I saw Ferris Bueller’s Day Off in a new light: Sloane probably just wanted to go home and take a nap the whole time.
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