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.

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?

I think the key phrase in this "as far as I know." You are not a part of their relationship, and they may want to keep certain details about their relationship private. Perhaps to avoid strange, gossipy interactions like this. There's also a possibility that she created that account ages ago, before she started dating your friend, and just forgot to delete it.

Whatever the reason, you're going to look incredibly nosey when you inevitably ask your friend about this. Which sure, go ahead, I guess. I totally get wanting to be a good friend but if this girl were looking to cheat on her boyfriend, she would probably be smarter about it.


I'm newly single and just starting to "get back out there," whatever that means. What is the etiquette in chatting up a girl? It has been a very long time since I've had to do this.

Speaking as a girl that recently suffered through a very unpleasant pickup, I certainly hope you're talking to these women and not shouting at them.

This is a tough thing to give advice on, because I feel like there is a subtlety and nuance to what I'm about to say that men are not always great at picking up on. You can talk to any girl that invites you to talk her. This usually means being a location that welcomes strangers interacting with each other: a bar, a park, one of those like, fun churches maybe? I don't know.

The thing is, women really don't like being hit on. It's unpleasant for the most part, and I can only speak for me here, but it has never worked. Not once. I just try to shut it down as soon as I realize that it's happening and then take my leave. And don't use a gross line. If you see a pretty girl out somewhere and she smiles at you and you feel like there's a connection that you can't ignore (there isn't by the way), then just tell her that. "Hey, I'm sorry to bother you but I just had to talk to you." I feel like that's the best way to go but I still think you'll get shot down more frequently than not.

If you are looking for a high success rate, I recommend online dating or joining a kickball team. My roommate is on a kickball team and everybody has sex with everybody.


Finding Out That You Smell

Break Up Promptly, and Always Unfriend

Maintaining a Relationship With a Dog

If you have questions about relationship etiquette, please send them to Ask Alison [at] The Atlantic (.com).