How to Date Multiple Women Honestly & Ethically – Andrew Ryan

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, relad 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.