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How to Casually Date Multiple People at Once

By / 01.14.13

You're not ready to wife her up but you still think she's pretty great. She's cool with getting dragged to concerts by your favorite bands and knows just how you like your protein shake. But you can't seem to shake the image of your bud's bangin' younger sister giving you the eye at the bar last weekend. Then, just as you're creeping through her spring break bikini pictures on Facebook, a chat window pops up. Holy BroBible, it's her! You exchange coy one-liners which eventually lead to phone numbers and just as your about to hit her with the “drinks tonight?” text, the “True Blood” theme song pops into your head. Damn. You debate about whether you consider yourself a free agent for a few minutes. No contracts have been signed, no titles given, so technically she's not your girlfriend. So do you explore your options while there's still time?

That's completely up to you. But if the roles were reversed, would you be cool with her casually getting drinks with her friend's older brother? If you haven't yet metaphorically “put a ring on it” and made it Facebook official, it sounds like you have reservations about this one. She's crazy about you and you know it. Don't you want someone you're just as crazy about though? Maybe The Facebook bikini queen could be it. You decide that you’d rather be a dating Casanova than a tied-down Romeo.

So you shoot her those two simple words, “drinks tonight?” to which she willingly agrees.

Now as you Acqua di Gio up, you wonder if you should be honest tonight and tell her about the girl dying to put a title on your situation. The answer is YES. Be up front about your relationship, however serious or not it is.

“I was just casually inside all of them”

But wait, won't she think you're a pig? Isn't there some sort of girl code she'd be breaking?

She'll think you're a way bigger pig when she sees those tagged pictures of you sleeping in a girl's bed with a cheesy caption ending in “<333″. And I hate to say it, but girl code is pretty arbitrary. Sure we get drunk and shout things like “Girl power! Sisters before misters! Hos before bros!” but most of those idioms are us referring to our direct group of friends. None of us want to be home-wreckers, but at twenty-something years old are we really wrecking homes and tearing families apart? Especially when you won't even publicly declare your relationship status to the Internet. Once the g-word and b-words come into play is when we tend to back off because we wouldn't want some other girl encroaching on our territory (and also we don't enjoy threatening Monday morning Facebook messages from your crazy g-word).

Anyways, if you're honest, she'll probably be pretty flattered that she caught your eye despite the watchdog who's usually carefully guarding you. And if you have no girlfriend candidates in your rotation, she’ll still be flattered that you want to take her out.

You might have to explain casual dating to her and voice your views on monogamy. I know it seems like something for old people or those brilliant sluts on “Sex and the City” but normal people can participate in pressure-free relationships with multiple people. Our generation seems to be obsessed with ownership over a significant other, insisting on virtually peeing on their territory all over the Internet. But why pee on one person when you can go around sniffing a bunch of people? Alright, bad analogy but you get what I mean.

Bottom line is, most girls love going on dates so they’ll understand that you might do it pretty frequently too. Also, knowing you date other girls eases some of those first-date jitters and it’s nice to know that other girls like you too (sort of like a letter of recommendation or a good Yelp review).

A few tips to remember when you’re out for an evening with a lovely lady:

1. OUT, when you’re OUT for an evening with a lovely lady. Meaning, do not ask a girl to come over and watch a movie and think that counts as a date.

2. Have a plan; tell her exactly where you’re taking her. Don’t ask her to make any decisions about what you two are going to do. She’ll undoubtedly say “I’m fine with whatever”. We like a man with a plan.

4. When in doubt, over-dress. Put on that button-up and wear your nice shoes (we notice these things)

5. Do not sit there and talk about yourself for 2 hours.

6. Avoid asking deep life-questions. (I once had a date ask me what was holding me back from achieving my dreams… Umm more wine please!)

7. It’s actually okay to ask her about her dating history and ex-boyfriends (just don’t pry too much)

8. If she tries to end the date early or not continue to post-dinner drinks on account of a “big day at work tomorrow,” she’s not very interested so take her home.

9. You should be able to tell if a first-date kiss is going to happen. She’ll linger after the goodbye hug, there will be eye contact. Don’t just go for it. But don’t be afraid to either if it’s called for.

10. Don’t text her later that evening. Let her take in what just happened. Wait until tomorrow afternoon to send that “I had a lot of fun last night. We should do it again soon.” text.

(Editor's note: Yep, she missed #3)

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