I’m in my late 20s and I've been dating an amazing guy for six months. We have amazing adventures together and incredible sex. He has awakened a part of me that I thought I had lost a long time ago. He makes me feel safe and appreciated like I have never experienced before. I don’t have a great track record with men and I feel so lucky to have found a man who I feel so supported by and loved completely.

Here is my problem: We met through a mutual friend who, at the time of our meeting, I had not had sexual contact with. He was with someone else at the time and we had spent some time together as just platonic friends, which we are to this day. He is a great guy and I consider him a close friend. My boyfriend and I hooked up once or twice before things got serious. We both have trust issues and it took a month or so before we started to see each other seriously. After the first couple times I hooked up with the man who [would become] my boyfriend... I ended up partying with our mutual friend and we had sex. We talked about it later and agreed that it wasn’t a good decision on both our parts. We remain good friends and neither of us has told anyone about it.

I feel guilty for not telling my boyfriend about hooking up with our mutual friend. It was before either of us had realized that we wanted to take things further. I don’t think our friend will say anything to him—he loves my boyfriend like a brother and is really happy we found each other—but it eats at me. Whenever my boyfriend gets upset and withdrawn, I imagine it’s because he found out. I know it was before we got serious and that it shouldn’t be a huge deal, but it haunts me. Keeping this secret is making me feel like a bad person and a bad partner.

Do you have any advice on how to deal with this situation if it ever comes out or how to deal with the guilt? Logically, I know it isn’t a huge deal, we weren’t serious at the time, and if a friend of mine told me this story I would tell them not to worry and just deal with it if it comes to light. I just care so deeply for this person and I would never want to hurt him.

Woman With A Secret

If you don't want to hurt him... don't tell him.

Sometimes withholding information—sometimes sparing someone the truth—is the loving thing to do. And in your case, WWAS, we're talking about information your boyfriend isn't entitled to. That hookup happened before you two got serious, it happened when you were still free to hookup with others without clearing or negotiating it with him. And he was free to hookup with others at that time too. For all you know, WWAS, there are things he hasn't shared with you; irrelevant things that might complicate your feelings for him if he told you about them.

So ask yourself: If your boyfriend hooked up with someone else during the period between you two starting to fuck and you two starting to date... would you want him to tell you? Or would you rather be spared? If it's the latter, WWAS, then Golden Rule this shit and keep your mouth shut. (But even if you'd rather know, WWAS, that doesn't mean he'd rather know. So you can still spare him.)

I would advise you differently—I would advise you to tell him—if this mutual friend was angry and/or vindictive or if the hookup was widely known and the subject of gossip within your larger circle of friends. It would suck for your boyfriend to find out from someone who wasn't involved—or to have it maliciously thrown in his face by your mutual friend—because then the pain of the hookup will be compounded by the humiliation of others knowing (and the assumption that others viewed him as foolish or pitiable). But it sounds like your mutual friend wants to stuff that hookup just as far down as far down the memory hole as you do, WWAS, which means the risk of your boyfriend finding out from anyone other than you is very, very low. But he's not going to find out from you. Because you're going to do the right thing by and for your boyfriend, WWAS, and keep your mouth shut.

And if he does find out... what do you say? "It happened before we got serious and I didn't think you would enjoy knowing or really needed to know, and I'm sorry you found out. It didn't change anything for me and I hope knowing about it doesn't change anything for you. And are you familiar with the 'memory hole' concept?"

I have been dating my girlfriend for about six months and she revealed to me that she once knowingly slept with a married man. She says he manipulated her and claimed he was unhappy in his marriage. She also says she felt horrible and called it off after the first time. She's regretful of the action and thinks karma will bite her in the butt. She also says she is a changed person and in a better place now because of me, cares for me deeply, and that I am the only person she has ever seen a future with. I will be honest: I am struggling with this. I understand it was in the past and it doesn't make her a bad person. But my sexual past isn't as sketchy as hers. Please let me know what you think I should do. I like her very much and want to stop dwelling on this.

My Girlfriend's Sketchy Past

Hey, WWAS? This is why you don't tell the person you're everything.

As for you, MGSP, here's what you do: You tell yourself that your girlfriend made a mistake. Then you remind yourself that everyone mistakes—you included—and while you may not have made the exact same "sketchy" mistake your girlfriend did, you've doubtless made your fair share. Then you refuse to dwell on this anymore. If you can't put it out of your mind—if your memory hole is too tight to cram in this irrelevant fact about your girlfriend—then you should break up with her. Not because there's anything wrong with (or sketchy about) your girlfriend, MGSP, but because there's something wrong with you.