Emily Yoffe, aka Dear Prudence, is on Washingtonpost.com weekly to chat live with readers. An edited transcript of the chat is below. (Sign up here to get Dear Prudence delivered to your inbox each week. Read Prudie’s Slate columns here. Send questions to Prudence at prudence@slate.com.)

Q. Weight-Loss Pressure: A few months ago, I met a wonderful man through an online dating site. He is a physician and we are both middle-aged. Our relationship has evolved quickly, and we have fallen in love. We spend most of our free time together. Ever since the beginning, though, he has expressed that he would like to see me lose some weight. He was quite thin himself when we met, to the point where it was unappealing (though I did not volunteer this to him). He had lost some weight after the end of his marriage, which had also involved weight issues on behalf of both parties. He has gained some weight back since we met while mine has remained the same. I am at the top end of a healthy BMI, or slightly above, and am certainly not opposed to losing a bit of weight, but I have the feeling from knowing which celebrities he idolizes that his ideal female body type is quite a bit thinner than I’d ever want to be. He keeps framing the discussion in terms of my health (generally excellent), which I think is a spurious low-blow. Apart from this issue, we are extremely compatible in all areas but I feel pressured and defensive when he wants to make a “deal” with me over losing some weight. I have tried to express my concerns but he says I am being too sensitive. Am I?

A: I’ll say you’re defensive. I’m a stranger and already I know you’re healthy, your weight is a smidge above the recommended, you’re willing to lose weight, but you’re worried your lover wants you to look like Sarah Jessica Parker, you resent his commentary on your body, etc. This does not sound like love. This sounds like what happens after that first flush of infatuation starts wearing off and you begin to understand why his wife is his ex-wife. Sure, parents of teenagers say that unless the kids’ grades improve their cellphone access will be curtailed. But you’re a middle-aged woman. Maybe if you renege on your half of the weight loss deal, your punishment will be your boyfriend curtails your sexual activities. What a fun situation that will be. It’s almost impossible to be happy, compatible, and relaxed with someone who checks your weight every morning and monitors your every mouthful. When you rightly have objected to this surveillance, you’re told you’re too sensitive. (Not to mention you have issues with his body.) I say forget the eating rules and just renew your membership to OkCupid.

Dear Prudence: Disgusting Dinner Companion

Q. Player: My boyfriend has described himself as a reformed “player,” meaning he was sexually promiscuous in his younger days. He’s pretty handsome and I still notice women looking him over when we’re out in public. It makes me angry that he doesn’t discourage this behavior. I guessed his password for his email and looked though all of his emails for the past few months. I’m pretty sure he’s not cheating on me, but he does have a few emails from women he’s friendly with which make me suspicious. I check his voice mails and text messages on his phone as often as I can and haven’t found a smoking gun, but I’m still worried. Should I confront him with my suspicions? I’d like to tell him that unless he can prove to me he hasn’t cheated on me, we’re through.

A: I think I know of a control-freak physician who might be available soon, and you two could monitor each other to your hearts’ content. I love the terms you want to present to your boyfriend: Prove to me you aren’t doing something there is no evidence you are doing. I think you should save you and your boyfriend a lot of trouble and just cut to the last part of your proposal. Tell him you are a compulsive snoop, you don’t respect his privacy, and you can never trust him. Say that because you care about him and want to save his sanity, you two are through.

Q. Should This Be Part of the Job?: Should a stay-at-home mom check in with her husband about what she got done that day? My husband thinks I should give him a breakdown of how I spent my time. 9 to 10 a.m., vacuumed and played with kids. 10 to 11 a.m., walked dogs and kids, cooked lunch. I say to him, your home and kids are always happy and clean. I shouldn’t have to account for my whole day. Who is right here, Prudie?

A: Did the listserv for Control Freaks Anonymous (and their loved ones) get misdirected here today? One of the reasons I could never imagine being a lawyer is because you have to account for your time in 15-minute increments. (“11:00 am to 11:15 am, brewed tea and stared into space.”) But at least that job comes with (or it used to) a compensatingly big salary. There is something really bizarre about a husband who comes home from a day of work and actually wants to look over the time sheets of his stay-at-home wife. I’m guessing this is not the first manifestation of his unpleasant micromanaging of you. Unless you can get him to see the lunacy of his demands, I think you two should find someone who bills by the 50-minute hour and get a professional to help your husband understand some boundaries.

Q. No Money Worries: After my former husband of 15 years and father of my three children committed suicide I was the beneficiary of a life insurance policy that, although not large enough to allow me to quit working, has eliminated a lifetime of financial worries. I have been fiscally responsible with the funds, but have allowed myself to work less than full-time hours and take off long school breaks with my children. I don’t feel guilty about doing this—I think it’s what my children need as they continue to process the loss of their father and work their way through their teen years. How do I deal with questions and judgment from people who comment on “how I never seem to worry about money”? They seem to be fishing for information and I worry that, by being vague, it is leading to people making up stories about how I was the recipient of “millions.”

A: I think the best response is to look at your interlocutor with a bemused expression, shake your head, and excuse yourself. If people you have to deal with—relatives, co-workers, “friends”—really are pressing you on your financial situation, you can answer with a kind of nonsequitur: “The kids are doing as well as can be expected after their father’s death. Thanks for asking.” You have no obligation to explain your personal life or your financial situation to nosy jerks.

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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