How to Date Multiple Women

When I was sixteen, my sister and I were helping my grandmother organize some old photographs. I’d just gone through a particularly harrowing breakup (it involved the bitter division of Wesley Snipes film bootlegs on VHS, to provide both historical and raw emotional context). I’d been with my boyfriend for six beautiful months of Demolition Man makeouts and I was never going to love again. My grandmother was less than understanding about it.

“You should be dating a BUNCH of guys,” she said, and held up a picture of one of her pretty sisters, as a teenager. “Sophie used to go with one boy Friday, another Saturday, and another on Monday.”

My sister and I exchanged looks. “Jesus! Aunt Sophie, right?” she whispered. “I know,” I said. “What a skank.”

To us, and all of our friends, agreeing to a single date with a dude implied consent to monogamy thenceforth. Going out with somebody else the next day would therefore be cheating, a cruel thing to do to your boyfriend on the all-important 24-hour anniversary. It was jarring to find out that our great aunt had basically spent her youth as the whore of Babylon. (Although, I guess she broke for Sunday, so there was that.)


I don’t know if it’s because of Cameron Crowe movies or disease panic or protracted adolescence, but my generation believed that when you really liked somebody, you should like them solely and exclusively, even obsessively. If a guy gave you a mix CD of Radiohead songs because it felt like giving you “a pint of his own blood,” and then he gave another girl a pint of his own blood, it sort of cheapens the gesture. You know, of giving somebody your blood. Metaphorically. It made Archie comics particularly perplexing. You’re going to date Veronica and her best friend and Cheryl Blossom? Ugh. Say goodbye to your T-cells, Archie.

A lot of my friends, male and female, followed this kind of “Medieval Courtly Love, With Blowjobs” model well into college, like knights and ladies with bitterly divorced parents. But for those of us still single, relaxed ideas about monogamy and the facility of the Internet have produced a new golden age of slutty aunts.

I know guys who date multiple women like they’re filling out an elimination bracket, and I know guys who date multiple women because they get easily bored by one set of nipples. More and more people I know prefer dating a bunch of people to one; you can be suspended in a kind of single-but-not animation that used to be reserved for old bachelors of indeterminate sexual orientation, and not be considered a jerky health risk.

But, at the same time, you aren’t a Branch Davidian cult leader and you can’t treat the world like a Waco sex compound, stocked with unstable teen runaways. The situation can be a minefield, so here are a couple of ground rules for being an ethical he-ho.


1. Make sure you give out enough information.
There’s a difference between gently avoiding the exclusivity talk and going into a relationship knowing you never want to have it. Blurting “I want to see other people” over first date calamari can come off as dismissive, so wait until it feels natural. Let her know you’re not looking for a girlfriend around the same time you’d tell her you had a terminal disease.

2. Don’t give out too much information.
There’s a difference between honestly and total transparency. Tell a girl that you’re seeing other people, don’t tell a girl that you don’t want to see One Day because you just saw it with a beautiful Pakistani accountant. That’s dishonest. You totally want to see One Day again.

3. Avoid social media.
A good rule of thumb is to always act as though you’re having an affair. Avoid friending women you date, and definitely don’t, like, Tumblr pictures of you making snow angels with a girl if you’re supposed to get hot cider with another that evening (in this scenario it is winter and you are charming!). Don’t ever give away your location—check in to a martini bar on FourSquare and you might as well have posted, “Greg just became the Mayor of Another Woman’s Vagina.”

4. Keep it casual.
If you’ve found a girl who’s okay with your tomcatting, congrats! Get all feelingsy, and you’re going to ruin it in a hurry. Don’t tell a girl you’ve “never met anybody like her” if you’d still like to meet a bunch of people like her and get blowjobs from them. And if you’ve got the kind of girl who reeeeeally isn’t looking for exclusivity, she doesn’t want you barfing your gross emotion germs all over her. Go feel elsewhere.

5. Bag it up.
I should not have to tell you this, but just because we aren’t making Boys on the Side-type films anymore doesn’t mean we’re out of the woods with sexually transmitted diseases. Did you see Contagion? I’m pretty sure that the bat and the pig that combined viruses to make The Contagion met on eHarmony and that I’ve had sex with them both.

Done responsibly, dating a lot of women is no longer considered outré. Enjoy the fact that, today, women are cooler than ever, because we are too busy stealing your screenwriting jobs, hoing around, and frittering away our fertile years to needle you for diamonds.

Article by Julieanne Smolinski