31 Jan 11

Sasha Speaks: Answering Your Most Private Dating Questions — Many Sex Partners?

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Dear Sasha,
I’ve just started dating a new guy that I really like a lot. I’ve had sex with a lot of guys for my age (I’m 25), more than I can count — do I tell him?

One too many to count.

Dear Too Many-
You know what are else too many to count? All the reasons never to tell anyone you’re dating how many sexual partners you’ve had. No matter what, it’s always going to be too many or too few and, either way, the truth is no one really wants to know.

I can give you a million pearls of wisdom on this one, but anything I tell you will just be a poor paraphrase of words I live by that I learned thanks to my favorite Kevin Smith film, Chasing Amy.

Ahem, and I quote…

“Men need to believe that they’re Marco-fuckin’-Polo when it comes to sex; like they’re the only ones who’ve ever explored new territory. And it’s hard not to let them believe it. I let my boys run with it for awhile, feed them some of that ‘I’ve never done this before’ bullshit, and let ‘em labor under the delusion that they rockin’ my world—until I can’t stand them anymore. Then I hit ‘em with the truth. It’s a sick game. The world would be a better place if people would just accept that there’s nothing new under the sun, and everything you can do with a person has probably been done long before you got there.”


The past is the past and you don’t need to drag it into bed with you, especially when it’ll only make your new boyfriend feel insecure. And that’s not because you’ve got a high number! You could’ve slept with only one other man and that would be one too many for most guys. And, here’s the kicker, if you hadn’t slept with any, you’d be vilified for that too. It would seem like “too much pressure” for most guys, proving, you can’t win if you’re the Madonna or the Whore so it’s better to not ask or tell.

If you’ve been around the block a few times, more power to ya’. Use that experience to your benefit and rock your man’s socks off. Just be sure to remember the immortal words of Ludacris: “They want a lady in the streets but a freak in the bed.” No need to let them know where you picked up those moves, just as long as you’ve got ‘em.


*Feel free to email us with any dating, relationship, love and sex questions you may have for Sasha.

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About Jennifer Kelton

Jennifer KeltonI did not wake up one morning and say “hey I think I’d like a man use my sweater like a towel, write a candid dating book, become a dating expert, the CEO and founder of a social dating site and have three blogs.”

All of this has happened in a slow burn and here I am. The good, the bad, the mistakes, way too many tears shed to count, lots of wine and oh my goodness a huge learning curve that leaves me much of the time saying, “I’m sorry but this is all new to me.”

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