The Five Date Rule

The Spice Girls exercise the Five Date Rule and safe sex.  Pretty sure.  Don’t pretend you don’t love this song.  I know you sing it in the shower before all fifth dates.  

I have a girlfriend (now married) who cheerfully drilled her dating life down to a science. She once went on 24 first dates between April and August. She met guys at Home Depot, at cocktail parties, at the dog park. She knew what she was doing. She had a first date outfit that consisted of skinny jeans, leopard print low-heeled pumps (she’s even taller than me, and I’m 5’10”), and a cream silk blouse. How she managed to wear this throughout summer I will never understand.

She had a set of rules she followed that seemed to work for her, and, at least from what I could tell, things backfired when she didn’t follow her own rules. For example, she once slept with a guy on the first date, but it wasn’t really a date, because he was a visiting friend she’d known for years. Backfired. One of her rules was the package check on date 2, something I’d never have the guts to do. During the good night kiss (assume you’re standing up at your door or something), she’d brush her hand across the guy’s package. Or maybe she cupped it or something. I’m not sure, and I could never do this because I’d assume the guy thought I was easy. But she made it work, and disqualified one extremely tall but weirdly disproportionate guy because of it. Success!

I’m always scared of guys thinking I just want to have sex, and soon, so I could never pull off the package check. The problem is, I do want to have sex, and soon, and early dating for me is a constant struggle to hold this urge back. A guy who kisses even moderately well will send me into the lost in desire neighborhood of my… brain. So, before that “2 Become 1” night, I’m just kind of awkward and cold in my effort to keep the guy liking me without revealing that I’m kind of slutty.

My friend with the package check also exercised the five date rule. “If a guy can’t wait five dates to have sex with me, he doesn’t really like me.” This seems like a patent truth. Five dates can happen over like, two or three weeks for people who really want to hang out – which isn’t much time to get to know someone when you think of it. My problem was always, if I really liked someone, I was struggling just to keep the three date rule that I followed as closely as possible in my twenties.

There are guys… like, one I call the “Brazilian Art Director Date Rapist”, who you give it up to on the second date because you realize they are jerks who aren’t going to be your boyfriend and you’ve never done it with a Brazilian. Backfired and led to an eight month boning hiatus (Note: “never did it with a Brazilian” not a great reason to have sex with a guy who you will later refer to as “rapist”). There are really nice unavailable/inappropriate guys who’re never going to be your boyfriend because they’re not boyfriend material but they’re sooooo hot. You don’t wait around for some other slut to snatch them up!  And then there is the guy (like, once every five years?) who you really like and kissing him is like seeing your future so you have to wait… you have to… but what if it’s really bad? So you better not wait more than three dates just in case. Which relates back to my friend’s package check if you know what I mean.

So, in my extended single thirties dating career, I’ve really worked on adopting the five date rule (except for the really hot guys that are clearly not future husbands – they have the golden ticket). And, it works. For one thing, I think I’ve dated guys that disappeared when they realized they weren’t getting the second date rule. And, they didn’t qualify for my second date rule (compartmentalized into fun casual boyfriend category), so who needs them if they can’t wait for five? Then again, it’s extremely difficult to be flirtatious and not implement the three date rule, and that’s something I’m working on, keeping the five date rule without seeming like a not before marriage rule. “I gotta go” for no reason right in the middle of something works, and is mysterious.

I had little practice implementing the five date rule until recently, because I had a lot of one dates with guys I didn’t exercise any rules on, and a lot of dates with super hot guys who are clearly not my future husband, baby daddy, or potential gardening/traveling partner. But, I’ve already benefited from the five date rule, and now I know I can do it. Because the five date rule prevented ME from sleeping with someone I ended up not liking. And not having slept with him has been the best feeling.

I could get into the details of liking and not liking this guy, brunch and too many drinks and stinky feet and things like that, but really, gossip is so useless. That guy was disco-ed, and I had the lucky feeling of not looking back on gross sex with him, or, even worse, good sex with someone gross. That’s so disheartening.


I’ve realized recently through actually implementing the five date rule, that something so beautiful can come out of it. No, I’m not talking about a boyfriend, cheeseballs. I mean, yeah, you’re right, that potential is there, but that’s not what I’m talking about.

I’m talking about the fact that if you keep a five date guy around long enough to sleep with him, and he passes the test – he suddenly becomes a one or two date guy. Meaning: you can’t stop thinking about him, he’s irresistibly hot, and you’re not even sure he’s potential husband material anymore because he’s so fucking sexy. In effect, you are crushed. And you’re crushed on a guy that took you out five times in earnest before you ever slept with him.

And that’s the only kind of guy I’d ever consider for a boyfriend anymore.

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