Q. Full of Regrets: I’m a man who didn’t have a girlfriend or have sex until I was well into my 30s. Now, I’m approaching 40, and am engaged to a wonderful woman with whom I have a marvelous sex life. But I keep playing over in my mind my dateless, loveless, sexless youth. I daydream about women I was attracted to when I was younger (who are now mostly happily married wives and mothers), and imagine what it would have been like to have been their boyfriend or husband. I imagine the interesting sex I could have had during what is for most people the most sexually fulfilling parts of their lives. It took me a long time to realize that not all women were like my mother. How can I stop this! I want to be content in the happiness I have now, not obsess over the happiness I could have had then.
A: If you read the Dear Prudence archives you will see endless letters from people who had incredible sex daily during their youth and now are wandering a middle-aged sexual desert. I’m wondering if your mother is the kind of person who is chronically unhappy with her current circumstances. If so, you don’t just want to avoid having a partner who is like your mother, you want to not be like her yourself. You are someone who was able to analyze your frustrating, lonely life and take steps to improve it. This resulted in your becoming happy. So now you want to wreck that by pondering just how much larger your total happiness could be if you had lived a different life. This line of thought will only be useful if you manage to be the person who finally invents a time machine. In the absence of that, stop contemplating the might-have-beens and focus on the wonderful, marvelous now.
Q. Re: Actually, we bill our time in six-minute increments: Be glad you didn’t choose the life of a lawyer!
A: And think of all those unemployed law school grads who wish they could measure out their life in six-minute increments. I wonder if supervisors look at timesheets and say, “Looks like a lot of bathroom time in there. Speed up that urine stream!”
Q. Teenage sex: I just find out that my good friend’s daughter is having sex with her boyfriend; she is 17 years old. Do I tell parents about this or keep it quiet ?
A: I hope that any parents of a 17-year-old, especially one who has a boyfriend or girlfriend, has talked to their child about safe sex and birth control. Yes, it’s hard to talk to people who are running in the opposite direction or have their fingers in their ears, but that kind of talk must happen. You don’t know if the parents know the kids are having sex. You don’t know if the daughter is being responsible about it. Unless you have information that’s more concerning than the fact that two teenagers on the verge of being legal adults are doing it, I think you should stay out of it.
Q. Sister Time—Minus the Sister-in-Law?: I have three wonderful sisters. We are all married and live within about an hour of each other. I need advice on how to deal with a delicate situation involving my sister “Kim.” Kim is married to a sweet lady named “Lisa.” For years, we have regularly planned sister activities every few months—usually dinner or a rare weekend getaway. My issue is that Kim always brings Lisa along to these sister gatherings. Before Lisa and Kim married last year, these were always sister-only activities. None of the rest of us ever bring our husbands or kids. We always include Lisa in other social activities and I really do like her, but I miss the dynamic of sister-only time. I have talked about this with my other sisters and they agree that they would prefer that Kim didn’t always bring Lisa. I feel we should discuss this with Kim, but I don’t want to hurt her feelings or make it feel like we are discriminating against her and Lisa. Any advice on how to bring this up gently?
A: You aren’t discriminating if everyone agrees to leave their spouses behind. But the complication is that while your husbands would run from an invitation to go on one of these all-sister get-togethers as if fleeing Carcosa, Kim’s wife obviously sees this as a fun night with the girls. So discuss this with Kim. Tell her there’s something special about the occasional sisters-only gatherings and since all of you leave your spouses behind you were hoping that Lisa would understand. But if Kim balks, it would be better to make Lisa an honorary sister than to have the gatherings without Kim or let them wither altogether.
Q. Accidentally Saw Sad Search History: Several years ago, I worked with a girl who I was friendly with. I enjoyed occasionally chatting with her but I never hung out or became actual friends. She left the company for another job a little over a year ago and I haven't spoken to her since. I recently checked the history on a work computer and realized that it was still linked to her Google account and I could see all of her recent browsing and searching. The searches were all about what to do when you feel sad and hopeless. I cleared it and logged her out. However, I feel conflicted—should I contact her just to see how she's doing, or should I just pretend this never happened? I don't want to tell her what I saw and it would be a bit odd since we were never friends, but I feel uncomfortable with ignoring the sad stuff that I saw.
A: Her solution to that hopeless feeling might have been to get out of the job she hated and find something better. You don't know anything about the nature of her searching. Maybe it was for herself, maybe she had a depressed family member she was doing research about. If you have information that someone in your orbit is suicidal, that's actionable. But you do not have to do anything about old Google searches from a former work acquaintance.
Emily Yoffe: Thanks, everyone, have a good week.
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