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How Many Guys Have You Slept With?

How To Answer The Question That Can Sink Your Relationship



Question From A Reader:


I’m a 19-year-old college student that kinda went crazy during my freshman year, mostly with the help of Grindr..  I’m tested frequently for HIV and the normal cocktail of STD’s but have never contracted anything.   A lot of guys have been asking how many people I've been with, lately.  A year ago, I would have proudly responded that I've only been with 4 guys...but now you'd have to add a 0 on the end of that 4 just to get close. 


Normally, when it bothers someone that I've been with that many people, their concern is not that I'm a blown-out whore, but that they'll get an STD.  I have always practiced safer sex (condoms, not swallowing) and I've even gotten into the habit of not letting guys finish in me. 


 I get tested every few months or so in spite of my practices and the fact that I have no signs and symptoms of any STDs.  I’m talking to a guy right now that I’m crazy interested in, but am scared that if he asks me how many guys I’ve been with he’ll be scared off.  When judgment day comes, what should I tell this new guy?  Help!


-Healthily Oversexed


Dear Oversexed:

The answer’s the same if he asked you how much money you made: NONE OF YOUR GODDAMNED BUSINESS.  


Of course, you can’t put it that way—there’s dick at stake.  So here’s how you finesse it:


*  Answer The Question With A Question. As in, “Why are you asking?”  Put the burden on him.  The people who truly want to know about STD’s might say, “I’m just a little worried about HIV and other ill-mannered microbes.”  Then you can simply say, “I get tested regularly and don’t have so much as a pimple.”


*  Assume his motivation is safety. If he says, “I’m only asking because I’m curious,” assume he’s worried he might catch a horrible disease like Age or Wrinkles.  Your answer: “I’m sensing you’re worried about STD’s.  No problem, I get tested regularly.”


*  If He Keeps Insisting, Question His Motivation. Once you’ve answered the safety issue, there’s only one reason he’ll ask:  He wants to judge you.  So don’t answer.  If the number is too low, you’re a loser.  If it’s too high, you’re a whore.  Consider acting out this scene:


Him: So, how many guys have you slept with?


You: Why is that so important to you?


Him: I just want to know more about you.


You: I’d rather talk about our sex life, not my previous ones.


Him: Why are you avoiding the question?  Do you have something to hide?


You: Tell me the right number.


Him: What?


You: The magic number you think is acceptable.  The number that keeps me in the  “good girl” category and the number that cages me in the “slut” pen.


Him: That’s ridiculous.


You: No, it isn’t.  Because you’re not interested in knowing the number.  You’re interested in knowing whether you’re dating an angel or a tramp.


Him: That is SO not true.


You: Yes it is.  No matter what I say, you’re going to judge me.



Okay, that’s a bit overly dramatic for somebody you hardly know, but you get my drift.  If he doesn’t give you an “acceptable” number, change the subject.  If he does give you a number, then you know he’s going to have a fit if you’re north of it.  At that point, you have to decide if you want to date a guy who’s more interested in what you’ve done than what you could be.


Ignite your love life with our Guide To Gay Dating

Michael Alvear • March 14, 2024
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