Miss Information: Do I tell my girlfriend I once slept with her sister?

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Dear Miss Information,

I live in a small city (70K) and use online dating as a way to meet women. About six weeks ago, I met a nice girl. We went on two dates, but I decided it wouldn’t work out. We scheduled lunch for the next day and I told her how I felt. She was not upset but asked if I still wanted to sleep together sometime. We ended up at her place that afternoon. I couldn’t believe it happened either. We said our goodbyes and that was that.  

Fast forward three weeks. I meet another woman. We’ve been on numerous dates, had a few sleepovers, but no sex. We added each other on Facebook and while looking at her page I noticed she is friends with the woman I previously slept with. I did some research and found out they are sisters with different fathers and different last names. Now I’m really bummed. Do I need to bring this up? Do you think she already knows? Once she finds out, is she going to end it? Should I message the sister and ask her to keep quiet? I really enjoy her and don’t want it to end because of something I did before we even met. — Fearing the Premature End

Dear Fearing the Premature End,

I’m not a fan of oversharing, especially when it’s an online-dating one-off. However, in this case, I would tell her. Why? Because it’s her sister, not a random friend. Because you run in the same circles. Because you live in a small town. Because the breakup with the other woman was amicable and you were the initiator. Because it only happened once and your current girlfriend was someone you didn’t even know. Because you didn’t have the information then, but you do now. 

How you act now that you have that information will be what sets the tone going forward. Contacting the other girl and asking her to keep quiet? Shady. Very shady, sir. That’s putting misters above sisters. Dicks over chicks. There are consequences that come with breaking that rule. Plus, even if you do ask her to keep quiet, who’s to say she’s going to actually do it? You barely know her. Her loyalty is going to go to her sister, not some dude she met online. 

You do have the option of never saying anything to anybody and hoping the sister does the same, but that’s also risky. What if the relationship gets serious? Are you going to avoid every Thanksgiving dinner and family reunion? What if dear sister’s the type to get loose-lipped and start commenting on your bedroom encounter once she’s had a couple glasses of Merlot? Do you want a solid relationship or one built on uncertainty principles? Remember what the first rule of celebrity PR — tell your story, or someone else will.

The good news is that it’s not that terrible of a story. Yes, sleeping with two women who share blood ties is creepy, but it only happened one time, it was a clean break, and you’re still early in the getting-to-know-each-other process. I wouldn’t dump you for that. I might feel awkward, sure. However, as long as you were cool and committed and didn’t leer at my sister every time we got together or called her name instead of mine in the sack, it’s all good. 

If she dumps you, so be it. At least you know now, before you were any more emotionally invested. You would have been dumped, anyway. The truth always comes out and you can’t go back in time and un-screw this woman. Who knows, maybe you can still salvage a fuck buddy relationship out of the other one if the sister you’re with now dumps you.

Have any of you ever been in this situation? How did you handle it?

Dear Miss Information,

I’ll get straight to the point: my girlfriend has a mustache. How do I ask her to get rid of it without hurting her feelings, getting into an argument, or having her hold it against me forever? She’s a great girl, but when cornered, becomes the queen of passive-aggressive remarks. — Boyfriend X

Dear Boyfriend X,

First of all, don’t ever call it a mustache. Say facial hair. Peach fuzz. Upper lip cozy. Anything but a term associated with Sam Elliott and motorcycle cops. That being said, the important part of figuring out an approach is figuring out your girlfriend’s mindset. When it comes to facial hair, women usually fall into one of a few categories: 

1. Those who don’t know they have it, and upon finding out they have it, are hurt, angry, and/or embarrassed. After getting over the initial shock, they’re more than willing to find a way to remove it.

2. Those who do know they have it, have done removal procedures it in the past, and have just been letting it slip lately. (Perhaps they had something more appealing to do with their weekend, like tour a waste processing plant or visit a friend in prison.)

3. Those who do know they have it, and don’t give a rat’s A, either because they’ve tried to get rid of it in the past and ran into problems or just don’t see the point of keeping up on something that’s just going to grow right back. Maybe they like the way they look or are a making personal or political statement — a sort of "fuck you" to the popular conception of beauty.

No surprise here: you’re going to have more success if your girlfriend is a 1 or a 2 than if she’s a 3. How to find that out? Try getting into a generalized discussion about grooming. Say her hair smells good and ask her what kind of shampoo she uses. Move on to soap, shaving cream, etc. Ask her if she’s ever had her nails done or legs waxed or had a spa day with her friends. Do it right, and you’ll sound like a naïve male curious about "all that girly stuff" that goes into making her look good. Do it wrong, and you’ll sound like a dude with a pedicure fetish or a burgeoning interest in cross-dressing.

Once you know a bit more about her, you can put a plan in motion. If she’s a 1, you can tell her straight out: "Hey, I don’t know if you’ve ever noticed, but you have a little bit of fuzz on your upper lip. It’s not a huge deal, but it would be great if you could remove it. If you want to get it waxed or something, I’ll go with you and get my (unibrow, back, knuckles, etc.) done at the same time." You could also do something more indirect, like buy her a gift certificate for a local salon that includes waxing as part of the package. Throw in an eyebrow wax so it doesn’t look as suspicious. 

There’s also speaking to the best friend or sister or having them be the fall guy. I know that sounds ill-advised: bringing in a third party. But it can work if your girlfriend is really close with this person and they promise not to reveal their source (you) and make it sound like their idea. 

The main takeaways here are to be gentle, complimentary, and polite. Expect hurt feelings. With something like this, it’s unavoidable. Give her time to vent and rant and reassure her without being defensive, even if she’s hurling insults about your haircut, bullshit media-brainwashed male gaze, and marginal wardrobe. She’ll wind down eventually. Then you can start working on a solution, even if that solution is to do nothing at all or a compromise, like bleaching or periodic waxing.

Readers, ever made an embarrassing request of a partner? What did you learn from it?

Have a question? Email Letters may be edited for length, content and clarity.