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About My Sexual History

Do I lie or tell the truth?


Advice Stop And Answer
Dear Natasha,

I’ve been dating a girl now for 3 months. This is the first girl that I’ve REALLY fallen for.  We are compatible on so many levels.  We talk for hours about everything.  Twice now she has asked me how many girls I’ve slept with.  Both times I just joked around and played it off.  I know the next time she asks, and I try to avoid the question, she is going to make me STOP AND ANSWER.

I want to be honest with her.  With this relationship, I don’t want to tell ANY lies.  But, if I tell her I fear that she is going to think different of me.  I used to be a ‘man-ho’.  I’ve slept with around 100 plus girls.  No girl wants to be with a man like that, right?  The thing is, I don’t want to be that guy anymore now that I have her.  So, what do I do the next time she asks me?  Do I lie to this girl who wants an honest guy and give a low number? Or tell her the truth, and risk this all being over?  I trust you Natasha!

“Kid Boston”




Kid Boston,

Before I give you my advice, I want to throw out a word in bold caps…HONESTY. EVERY WOMAN at some point gets petrified that she settled with a man that she can’t trust. Honesty, honesty, honesty is not only what every woman wants, it’s what every woman needs for her sanity. The problem is….although every woman wants the truth, not all women are mature enough to handle it.

If I was your girlfriend, AGAIN, I would just want the truth. If you told me that you slept with over 100 people I might say jokingly, “ew….that’s gross.” I might not even be fully joking! Personally, I haven’t had a lot of partners because of my philosophy on sex (I’ll explain it another day.) Because of MY beliefs, it’s hard not to have that initial thought filled with some judgement. But, the 3 things that matter to me, is that you were able to be honest, take a little teasing, and that I’m enough for you. I thankfully have that level of maturity now where I understand that you not only have your own beliefs about sex, but that you had a life before me.

I’m not putting your new girlfriend down, I promise, but there is already a maturity issue that is present in your relationship. The fact that she keeps pushing and feels like she needs to know, tells you that she IS going to allow your past effect how she feels about you. Again, I know what you did in the past should have nothing to do with this relationship, but is she mature enough to get that?

I hear from guys, all the time, that have the same story as you, about being a “man-ho”, but suddenly, they found a girl that makes them want to leave that all behind. Your new girl should feel lucky that she was the one girl to make you want to change things about yourself.

Here’s my advice. Tell her what you told me. This relationship is starting off so special that you wouldn’t think about taking it to the next level with lies. Tell her in the past, you’ve not always been honest, for fear of the judgement that usually comes with it. Tell her that you are willing to take a little judgement because you’re not going to lie. Tell her you understand that every girl wants and needs the truth in a relationship. And although you don’t think it has anything to do with how you are going to act in this relationship, you’re going to tell her.

I believe that she is going to be shocked. She will probably joke or show her disgust, but just allow it. Don’t get angry. She has a right to process this new information. Then ask her to file it away, because bringing it up will only do damage. Ask her to focus on the fact that she has an honest man. Tell her that because she is special, those old days are gone. HOPEFULLY, she will be mature enough to keep moving forward. If not, and she keeps bringing it up, I would tell her that you don’t want to be judged for your past any more. And if she still continues, I would honestly step out of the relationship. It’s only 3 months old. And if GIRLS ARE LOOKING FOR HONESTY in a relationship, GUYS ARE LOOKING FOR AN AWESOME GIRL THAT’S NOT GOING TO GIVE THEM A BUNCH OF BULLSHIT!

Give her a chance to handle the truth….if she can’t…..bye Felicia!

Lemme me know you what end up doing…..glad I could be here for you….remember IMYAGIRL!!



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