Sasha Speaks: Answering Your Most Private Dating Questions –- I’m Double Dipping?

  • Posted on: June 11th, 2012 by

“Dear Sasha
I’ve been dating this girl for the past few months. Things are pretty serious, we’ve slept together and say ‘I love you,’ and it’s all great, except that I used to go out with her friend and that makes things a little tense and weird from time to time.

How can I alleviate the tension?

Doug the Double Dipper

Dear Double Dipper-

I can practically smell the stench of awkwardness from here. It’s thicker than the fog of Dolce Gabbana cologne coming off a GLT-ing guido in Ed Hardy fist pumping his way through a Saturday night on the prowl.


First of all, I’m gonna guess that “a little tense and weird” is your guy speak for what most people, especially women, would deem a major s*%tstorm. And I don’t think you packed an umbrella. If you’ve been naked with two women who have to co-exist, the only way to alleviate the tension is to make sure the girl you dated first gets married or starts doinking George Clooney so she won’t have to wallow in the fact that you’ve moved on with someone she knows.

And speaking of, who is this hussy you’re dating?!?!

She violated Girl Rule Numero Uno: You don’t date your friend’s man! That means guys your friends have dated, slept with, made out with, or even crushed on.

Sure, guys have no problem passing a girl along to their friends, but women don’t operate like that.

If I found out one of my girlfriends hooked up with Simon Retner-Warner, who I “went with” for two days before dumping him during third period French class in 7th grade, I’d be pissed. I don’t care if it happened in junior high, I Columbus-ed that ass. I stuck a flag in it and now it’s done.

There are billions of people on this planet; why recycle booty within a friend circle? Even Al Gore can’t get behind that kind of behavior. Besides, how weird is it that now the two of them can sit in a room and say things like, “Don’t you love it when Doug does A, B,C and D?” Girls talk about everything, in vivid, gory detail. The fact that these women can compare notes on your sexual stats doesn’t make them bond, it makes them bitter.

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

  • I’ve dated two girls that have known each other, and the second one never brought the issue up. How likely is it that she wouldn’t show concern but it would be an issue that caused her to lose interest in me?
     – Dave

  • I have to say, DDD…..I agree with Sasha!

    You’ve put yourself in quite the compromising position, so alleviating tension may be near impossible.  Unless, of course, the first girl does manage to move on in epic proportions, similar to the examples Sasha listed.

    The real problem is not the tension you’ve both created.  The real issue – in my humble opinion – is that you’re now seeing New Girl who has absolutely no issues with dating her friend’s ex.  She flippantly ignored the fact that her friend may have been in love, may have gotten hurt, and may be hurting even more so now that you’re in a “pretty serious, we’ve slept together and say ‘I love you,’ it’s so great” relationship.  It hurts to see your ex with someone new.  Hurts even more when they seem so happy.  STABS you in the HEART when it’s your friend.  New Girl doesn’t mind – she’s in love! 

    If New Girl started seeing your friend after the two of you broke up, would that be OK with you?  I mean, after all, New Girl is trying hard to “alleviate the tension” between you and your friend……

    I’m not trying to say you should dump New Girl.  All I’m saying is: there will probably always be a little bit of friction, like it or not.  That’s the nature of the beast when dating two friends.  Take the humble approach – acknowledge that you double dipped, be respectful of Old Girl’s feelings and emotions, and move on with life.  🙂

    Good luck!


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About Jennifer

Jennifer Kelton

Jennifer Kelton CEO / founder LLC is a Los Angeles native and a pioneer in the worldwide dating industry, investigating the game of love while providing encouragement and support since 2007, starting with the acclaimed dating book Don’t Use My Sweater like a Towel. An accomplished CEO, visionary and entrepreneur, Kelton’s work in the […]

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