Advicereality check

Reality Check

My best friend just got engaged. We have known each other since we were little and always did everything together. Her family is like my family. We did everything together growing up, and when we both decided to go to college, we ended up in different places. I went someplace nearby, and she went out of state. We didn’t see each other as much, but we talked all the time on the phone and still told each other everything. After school, I spent a year living out west with another group of friends, and my best friend came back home. She got a job and started dating this guy, and she told me all about him and he sounded great. Soon, she was telling me that she was in love, and that they were talking about moving in together. When I came home and finally met him, I was horrified because I realized that he and I had had a drunken one-night stand back in college. I never told her about it at the time, because she’s always been more conservative than me and I didn’t want her to lecture me or think I was a slut.

The thing is, he and I have mutual friends, and we had one fun night, and then it never happened again. We didn’t really see each other very often, and when we did it was never awkward because we both knew that nothing was going to come of that night, and before this I didn’t even know his last name. Which didn’t matter, except that if I had I would have known that he was my best friend’s new boyfriend, and I would have been prepared. So, when we were “introduced†by my best friend, we both smiled and said “Nice to meet you,†and he said “You’re friends with Jenny so-and-so, right?†and I was like “Yeah.†Neither of us said anything, but in the moment it was like we had mutually agreed not to tell my best friend and his girlfriend that we had a past. I don’t think any of our mutual friends even know it happened, or if they do they have never said anything. But now I’m starting to feel guilty, like I’m hiding something from my best friend, and I don’t know if I should come clean before they get married. It has been almost a year since I have been home, and they are probably going to get married in the fall. I feel terrible. I don’t want to hurt her, but I don’t know if lying is the answer. Should I talk to him? To her? I am confused and I feel guilty. Please help!


First, don’t feel guilty. This is a weird situation, and you reacted in a moment of shock out of a desire to protect your best friend’s feelings. Even though you are also covering your own ass, there is no malicious intent in your secret and you are not a terrible person. You said you never told her about the one-night stand because you basically think that she would be morally opposed to it, right? You didn’t owe it to her to tell her. Now, do you owe her to tell her you slept with her future husband? I don’t think so.

I think if you did, especially after all this time, you would certainly hurt her and potentially ruin her otherwise happy relationship over something that happened ages ago and was virtually meaningless to both you and him. Even if she did forgive you, she would certainly think about it, and it just seems pointless to risk making her feel bad. Imagine those thoughts invading her subconscious on her wedding night. Crappy, right? And for what? The only thing you need to make absolute certain of is that he has no intention of ever telling her. And if he really cares about her, which I am assuming he does, then I can’t imagine why he would want to do it either. Sometimes full disclosure is just a bad idea.

I work in a small company. I am very close to my boss and all of my co-workers, and we are very much like a family. We are involved in each other’s lives outside of work, our kids play together, and some of us go to church together. Our spouses know each other, too, and I value all of them and their roles in my life. Recently, my boss and his wife have been having problems. I know this because my wife and his wife are very close, and they talk, and then my wife talks to me. I hope you will understand that this is not in a gossipy way. These people are our dear friends, and my wife is talking to me to try to understand what might be happening. I can’t say that I do understand, because my boss has not indicated to me that anything is wrong.

Since this has been mentioned, I have started noticing that he is paying a lot of attention to a particular woman that we interact with. I don’t want to jump to any conclusions, but I know that things have changed. He calls this woman more than he ever used to, and they have more meetings right now than we possibly need with how little business we’re doing with her company. I don’t know what to do because I can’t admit that I know that they’re having trouble or I’ll be betraying my wife. At the same time, I really feel like if it isn’t too late I would like to bring him back from the precipice he seems to be standing on. Add to this the idea that my job could be in trouble, and I have a hot mess on my hands. I don’t know what to do. Should I talk to him?

Ignorance Is Bliss

If you decide to talk to him, I would approach it in a “Hey, I noticed you seem to be spending a lot of time with Judy†kind of way, rather than a “My wife tells me your wife is miserable and your marriage is on the rocks†way. Better yet, skip the accusation and try going with concern. I think if you are really close to this guy, and you really care about him and his family, you should talk to him. Maybe tell him you’ve noticed his wife seems sad? Ask him if things are OK, if there’s anything he wants to talk about, or any way you can help. If he opens up, great. If he doesn’t, then give him the old “My door is always open†line and back slowly and quietly away. You can’t help unless he wants help, and you certainly don’t want to get fired.

Got a question for Jyl? Submit your anonymous inquiry via the Reality Check form