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Dating Tip of the Day


A lot of guys email me asking me how I handle questions about my sexual history from girls. The short answer: I feel them out. Some girls can handle it, some can’t.

The more in depth answer: Well, the question that most women love to ask is; “How many women have you slept with?” This is a no win question. If your true answer is low- she’ll assume your inexperienced with women. If your answer is too high she’ll assume your a player just looking for sex.

This is a question that you’re best off to avoid answering. Just deflect the question with sayings like “it doesn’t matter,””haha wouldn’t you like to know.” I like to make a joke out of the question. I’ll tell her I’m a virgin. Or I’ll say something like “Only a few that I was in love with”(with a wink and smile) If you’re absolutely forced to give an answer I would stick with 8-10. Personally I tell girls mid 20’s but thats because I have a reputation amongst my circle and can’t really get away with saying less.

Also, never ask a girl how many guys she has slept with. I know its a tempting question to ask… but trust me no good can come of it. I get nauseous if any girl I’m dating has slept with more than 4 guys. I don’t want to hear it. I had a girl tell me 14 once, and that was the last time I asked. Plus if her numbers to small it will just make your seems that much bigger.

As for the other questions about your sexual history… you really have to feel the girl out. Personally I’ve done shit that will make most girls run for the hills.. unfortanately when I’m dating a girl I really like I feel compelled to be honest with her. I usually let things slip out little by little, some things I never tell (the sex parties in Brazil) some things I wait till she’s in too deep to get scared off (sleeping with 2 girls in the same night) But you have to be the judge of what your girl can handle. And what you can handle. Once you start opening up she will too. And sometimes you’re better off not knowing your girlfriend once got tag teamed in the bathroom of a frat party.

About Bobby Rio

I'm Bobby Rio, one of the founders of TSB. I tend to write about what is on my mind so you'll find a mix of self development, social dynamics and dating articles/experiences.  For a collection of some of my favorite articles check them out.

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  1. ScottUA

    September 18, 2007 at 8:22 pm

    I like to go way OVER the top when I describe. Something like “10,000, me and Wilt Chamberlain are having a competition”.

    Definitely think this conversation should be avoided at ALL costs unless you’re thinking long term.

  2. Ha$h

    January 13, 2008 at 12:54 am

    Way over the top really helps diffuse the situation I’d agree, I like to use that too.

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