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Dear Breakup Girl,

I am a 30 year old woman who is currently in a relationship.. My problem is not the relationship but rather, my past. You see, I was an escort for 3 years. I left the business two years ago and have returned to grad school. My future is bright but sometimes I'm afraid that my past will come back to haunt me, especially where any future relationships are concerned. I'm not really ashamed of my prior occupation: I did it, I liked it and it helped me to get to where I am now and as I said before, its a good place. Not ashamed, but certainly aware that society (and men) frown on women who practice this particular trade. I'm essentially happy but afraid that if things progress with my boyfriend I will have to decide whether to tell him or not. If not him, then the next one... What do you think, should I keep quiet and risk exposure at a later date or be honest up front (if or when the relationship progresses to that point) and risk losing him????

-- Kristi

Dear Kristi,

Oooh, I love this one. Good call, good attitude, good news, good question.

First of all, you're right. I'm not going to get Pollyanna on your ass: he might freak. (See Kevin's letter.) I'm not saying freakage is right or wrong, I'm just saying he very well might. Reality.

Still, I think that you are going to have to tell him (or whomever) at some point, yes. When? Well, on the one hand, there's Too Soon. I do not think that this is a disclosure that need predate involvement. It is your business, your choice, your past. Arguably, it does not affect the current relationship the way, say (eeeeuw, sorry, I don't mean to equate here, but) an STD would. So I think you're fine so far.

But then there's too late. I don't think anyone wants any potentially major (though again, maybe it "shouldn't" be, but it might be) secret kept from anyone they're sincerely, profoundly involved with. Any such revelation could crash as a "How could you have kept this from me?" shocker.

So where is the precise point in between? It's where you've built up enough trust to cushion the [potential] blow, but not so much that the [potential] blow rends that selfsame trust. On what exact day that will fall, Kristi, I'm not quite sure. But I will tell you this. I recommend that you date only guys whom you could see telling, at some point, in the first place. I recommend that you see that there is a middle ground here: that he could be both thrown for a loop and able to deal. And I recommend that you get that dating you would be worth that.

Love,
Breakup Girl

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