7 Rules for Dating Several People At Once

by Rebecca Santiago

So there are two ways to eat dinner. (Actually, there are quite a few ways to eat dinner, but I am trying to craft a metaphor here, aight?) You can go the traditional route and order a behemoth of an entrée — something safe, like eggplant parm. It will be extremely delicious and comforting, but it might get kind of boring by the 15th bite. Or it might not. You never know with eggplant parm.

The second option is ordering tapas — a taste of this, a nibble of that. You’ll experience an array of flavors, and though you won’t love them all, they’ll keep you intrigued. I guess what I’m trying to say is, maybe sometimes you want to date a lot of people at the same time, in the same way that you might want to eat a lot of small plates instead of just one entrée, because it can get very 15th-bite eggplant parm-y to just date one person. There is also a chance that I’m terrible at metaphors.

Either way, I think we can all agree that dates are way harder to juggle than tapas. Tapas don’t peer over your shoulder while you’re texting, or get sulky when you say "Sorry, Saturday's booked but how about Tuesday?" And while tapas are sometimes a little heavy on the cilantro, they’re very rarely ever high-drama, as dating several people can sometimes be. Fortunately, the list below will help you to survive even the craziest of dating rosters. Good luck and bon appetit.

1. You don’t need to be freakishly upfront, but don’t be a dick, either

Many people will tell you that honesty is the best policy when it comes to dating. It’s probably true, but if you’re bad at confrontation and slightly aroused by minor espionage (what?), you might not feel like being super-upfront with your casual partners about your other casual partners. This is fine, as long as you’re not a total asshole about it. You’re under no obligation to wave your date-filled calendar in the air or anything.

That said, if a date asks you if the two of you are serious/exclusive/just chilling, don’t lie. You don’t have to hand over your diary or anything — just say, “Yeah, I’ve been on some dates lately. All casual, though. What about you?” And if you’re not on the same page, know when to cut it off. There are plenty of other fish in the sea, and you shall sup on one of them next Thursday with that programmer from Tinder at the cute Mediterranean place uptown.

2. Put your phone on lockdown (or, like, away)

If your date doesn’t know about your other paramours, you don’t want to make him suspicious, and if he does, you don’t want to flaunt them. Turn off the text preview on your phone, and hey, why are you texting on a date, anyway? Knock it off, Millennial.

3. Date very different people who would probably never, ever hang out with each other

You really shouldn’t be dating eight tortured musicians who live within a five-mile radius of one another. Anyway, the whole point of dating is to try out totally different types of people. Consider an artist (always free, no money), a banker (free on weekends, nice dinners), a bouncer (good club access, different date shifts), a marketing dude (free for happy hour, split the bill), whatever — so long as you avoid seeing two of a kind.

4. Schedule smart

As with most things in life, organization is key. Some people are able to swing two rendezvouses in a day; others need weeklong gaps. The most stressful thing you can do is overbook yourself, so try to set realistic limits for yourself.

5. If you don’t schedule smart, go out for tapas

Sorry, I know the tapas joke was really dumb and I should just let it die, but this is actually a pretty good tip! Because if you forget to schedule smart and instead plan a 2 p.m. lunch date and a 7 p.m. dinner date, you are not going to want to order two eggplant friggin’ parms. You aren’t. With small plates, you’re less likely to overeat and consequentially retch all over your unfortunate second date. See? No retching = great tip.

6. Have safe sex


7. Kiss and tell selectively

You know what’s uncomfortable for three people? Telling your coworker about the awesome date you had with Dude A, and then bumping into that coworker when you’re out with Dude Q (that’s right, Q), and having your coworker go, “Oh, you must be Dude A!” Also uncomfortable: talking about someone you’re dating suuuuper casually with a vague acquaintance, and then realizing that the two of them are really good friends, and then having to navigate that weirdness. Tell your inner circle whatever you like as always, but think twice before dishing at the office candy basket. That’s a pretty watertight life motto, actually.

Main image: Beth Dubber/FOX