10 Do’s And Don’t’s Of Dating Multiple People

Okay, so I jut turned 26 years old. It’s not “old-old” in the scheme of the human experience/geologic time, but it feels kinda old to me right now. I’ve had a few serious relationships, and some of them ended because of my own shortcomings, some ended because of his shortcomings, and some ended because I/him/we were so desperate to BE in a relationship that we took what we could get, regardless of actual compatibility. Nonetheless, after the last one, I realized that I might be in a stage of my life where I honestly can’t rely on my own judgment when it comes to men. It’s pathetic, but at least I can admit it. So, I’m doing this new thing where I just openly date a heap of dudes, and am going to remain ACTIVELY AND WILLFULLY SINGLE for at least a year. I’ve been doing it for about 6 months. Here’s what I’ve learned so far:

DO: Date multiple people.

If you’re doing the single thing, go on with your bad self and GET SOME. There’s absolutely nothing wrong with seeing multiple people at the same time.

DON’T: Feel guilty.

If you’re upfront and not being shady or secretive about your actions, there is no reason to feel guilty. There’s a major difference between confessing your love for someone and going out to dinner.

DO: Attempt to get to know said people, rather than just sleeping with them.

Dating multiples is one thing, fucking multiples is another. Personally, I’ve got love for both sides, but if you’re a relatively young person who’s just “trying to find yourself (gag), I highly recommend making a sincere attempt at getting to know those you choose go out with. After all, isn’t part of finding yourself figuring out what kind of people you’re really into?

DON’T: Develop feelings.

I need to clarify here. Having feelings isn’t a bad thing. Call me crazy, but I encourage it. I suppose what I mean is that if you’ve already established that you’re “keeping it casual, man,” then…KEEP IT CASUAL. Don’t say you feel nothing when you actually feel everything. This point is one I’m still working on myself, so don’t feel bad if you can’t be cool as a cucumber 24/7.

DO: Use condoms, for Gods’ sake!!

I don’t know about you, but I am not in college anymore and have thus graduated (so to speak) from the not-very-nice-but-usually-free-or-cheap student health services to the “hey-cousin-do-you-have-any-extra-Monistat?!” version of sexual health. No need to be tossing blame left and right when a particularly nasty strain of Chlamydia comes around. Wrap it up, and you can remain blame-free (and know who to cut out of your little black book for fucking around). Note: If you’re a female, now would be a great time to start keeping a menstrual calendar. I know, I know — it sounded like a bunch of barefoot hippy nonsense to me too, until I, a clockwork menstruator, was 10 days late last month after only having sexy relations with one man who, by the by, has HAD A VASECTOMY. Did I think I was going through early menopause/had cervical cancer/was possibly carrying the next Baby Jesus? Yes, yes, and yes. Did I have a hysterical breakdown and call said-vasectomied man crying and asking about the statistics of vasectomy failure? YES. Was I humiliated? Did I set a calendar alarm for the projected arrival date of my next period EVERY MONTH FOR THE FORESEEABLE FUTURE?!! YES YES YES, GOD, YES!!! <<<This is your brain on bloodthirsty feminine hormones. Don’t make my mistake, ladies!

DON’T: Kiss and tell to someone you’re kissing.

This should be obvious, but sadly, for many it’s not. No matter how much we insist that “it’s all good, bro, we’re like, totally homies!”, we don’t mean it, not really. Perhaps this one is geared more toward the ladies, but I feel pretty confident in assuming that no matter the gender, we as humans don’t like sharing private parts. Or at least, knowing that we’re sharing.

DO: Clean up your tracks.

Like I mentioned earlier, no one wants to know that they’re sharing. Even if you, your partner, and his/her mother knows you’re dating and/or sleeping around, it’s common courtesy to erase all traces of another man or woman before you share your bed/house/car/whatever with another. I had the misfortune of discovering a “hey sexy, thanks for the fantastic weekend XOXO” note at my favorite lovers’ place recently. It sucked. Presumably, it sucked just as much for me as it would have for Miss XOXO to discover Loverman’s growing collection of my sexy panties that he keeps in his bottom dresser drawer. I was pissed.

DON’T: Overbook.

Never schedule one meeting on top of another, unless the first one is someone you’re just using for free dinners (oh, get off your high horse and stop pretending like you’re never done it and/or aren’t jealous you didn’t think of it first) or drinks to get you loosened up for the next. The chances of overlap are just far too great, and the consequences (A.K.A.: humiliation and/or looking like a total dickhead) are even greater.

DO: Be honest.

But only if you’ve been asked straight-up about your intentions, feelings, or any of that dumb goopy stuff. If someone wants to know if you’re seeing other people (and you are), you should be as honest as possible. If you were any sort of decent human being, you wouldn’t want to hurt their feelings anyway, right? On the plus side, if they get so pissed off they won’t sleep with you anymore, you have a couple other to fall back on, right? Note: if they’re drunk when they ask you, they might not really want to know. Whether they really do or not is irrelevant, this is NOT the time to confess to schtupping other people unless you want to spend your Friday night cleaning MAC liquid eyeliner off your shower tiles, or cuddling when really all you want to do is smoke some weed and eat an entire pizza….in bed, alone.

DON’T: Assume you’re the only one.

For me, the ideal casual relationship is one in which I am free to be my naturally flirty/horny/slutty self, and the man I’m seeing is so tormented by my beauty, intelligence, and sexual prowess that he couldn’t imagine sticking his penis into anything other than me. Sad to say, this ideal relationship is totally un-fucking realistic. If I ever met a guy like that, I would think he was the biggest pussy ever and never fuck him again. So don’t be a pussy, and don’t casually date if you can’t handle it.

There’s nothing wrong with being a Monogamous Morgan or a Skanky Shannon — you just gotta figure out which one you are so you don’t end up getting hurt. Because, after all, this is all about you. You’re not obligated to do anything other than look out for yourself, so go out there and GET IT, GIRL/BOY!