Ask Alison: Should I Tell Her I've Paid for Sex in the Past?

Good advice from someone who is terrible at dating
(Shuji Kajiyama / AP)

This girl and I have been dating for a few months now. Things are going really well, and I could see myself being with her for a very long time, maybe even marrying her. The only problem is, I have a secret. I went through a bit of a dry spell in my late 20's and ended up paying for sex with multiple sex workers many times. I don't know if this is something I need to reveal to her, or something I can keep to myself for the rest of my life. I don't even know where she stands on the issue of prostitution, but I'm guessing if she found out, she would not be happy. What do I do?

First of all, don't use the phrase "I have a secret" only to follow it up with the fact that you saw a couple prostitutes. It's anti-climactic storytelling. Did you at least fall in love and go on a crime spree together? Because if it's just that you paid for sex, I don't really know where the drama is.

When couples give each other their dating history, they're mostly going over the big landmarks: First Love, The One That Broke Me Forever, Longest Relationship, etc.

Hey man, your past is your past. It's of course important to be open and honest with your significant other, but that doesn't mean sharing every sexual experience you've ever had. Sometimes people want a full rundown, and sometimes they want to arrive in their life brand-new just out of the package. When couples give each other their dating history, they're mostly going over the big landmarks: First Love, The One That Broke Me Forever, Longest Relationship, etc. Even then, you're looking for patterns or things that you learned about yourself from past situations, not how you had sex with your exes.

However, based on the way you worded this question, it seems like this is weighing heavy on your conscience. There are certainly some factors that might make it important for her to know. If you got an STD, although that could have happened with any of your partners, she should absolutely be made aware of that. Or if she is so morally opposed to the idea of sex for money that if she knew about this, she wouldn't want to be with you. Or finally, if the guilt of this terrible, shameful, fairly common (and not particularly terrible or shameful) thing is tainting your relationship then sure, I guess confess to her.

If none of these are the case, I encourage you to keep this one to yourself, unless a little Dick Whitman shows up. She doesn't need or want to know, I promise you.

I've recently started online dating, which is going sort of okay; it has its highs and its lows. My question isn't really about me, but about my friend's girlfriend, who has an account on the site. I just sort of stumbled onto it and as far as I know, they don't have an open relationship. Should I tell my friend?

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Alison Agosti is a writer living in Los Angeles.

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