Dear Prudence

Short Haul

Prudie advises a woman dating a 26-year-old divorcé whose last girlfriend was a mother of three teens.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

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

Emily Yoffe: Good afternoon. I look forward to your questions.

Q. Boyfriend Was in the Cougar Club: I am 25 and recently began dating a wonderful divorced 26-year-old man. I grew up very sheltered, whereas he has had a long and colorful sex and romantic life. Recently he told me that prior to dating me, he had a several-month fling with a 47-year-old woman with three teenage children. He had been planning on entering a romantic relationship with this woman, meeting her children, and introducing her to his family, who were mortified by the relationship. Ultimately he ended it because she had issues with alcoholism. I understand a fling, but I am worried that seriously dating such a person shows a lack of judgment. Am I too conservative, or is my boyfriend’s ex-flame a sign of a character flaw?

A: An alcoholic 47-year-old woman with teenagers who thinks a guy in his mid-20s is a good prospect as a partner definitely has some judgment and character flaws. I can’t rule on your boyfriend because he’s still so young, and many young people with floridly adventurous sexual youths settle down to contented monogamy. But to have already been divorced by age 26 and to think that a fling with a troubled woman a generation older has long-term potential indicate that your guy still has a lot of growing up to do. You’re only 25, and you’re having fun with someone you’ve been seeing for a short time. So continue to have fun, while you take it very slow emotionally.

Q. Relationship With an Engaged Man?: I am in my early 30s, and a few months ago I moved to a new city where, through a mutual acquaintance, I met a great man who I had a lot of chemistry with. Shortly thereafter he got engaged to his then-girlfriend. I have become relatively close with both of them, and they are both amazing halves of the couple. But independently they have both expressed their major concerns with their partner and they seem like they fight a lot. I am fairly certain that this man has feelings for me, and since his fiancée travels frequently, he has invited me to several social events. They are getting married in a month, and I’m not sure how to react to his invitations. I think it’s possible that something will happen between the two of us at one of these parties, and I don’t want to be a home-wrecker, but I also feel like we are a much better match than him and his fiancée. Should I turn down his invites or see what could happen with this guy?        

A: You feel like “something” might happen if you take him up on his offer to go on a date while his fiancée is out of town. I assume if “something” happens it will be because you decided to let it happen. My advice is to decide not to and to turn down his offers. Trying to break up the impending marriage of new friends—who may indeed be mismatched—is not a good strategy for long-term happiness. If this guy recognizes that your coming into his life has prompted a timely reassessment of his priorities and desires, fine. But it sounds like he’d just like to have some fun pre-wedding, and maybe even post-. Instead of your chemistry illustrating that you two are a better match than the one he’s made, his behavior is showing you what a bad prospect he is. Act accordingly. 

Q. Airplane Etiquette: What’s the etiquette for airplane windows? If someone else is sitting next to the window, would it be rude for me to ask him or her to close it? If I’m sitting next to the window and someone asks me to close it, would it be rude to refuse? Also, if someone asks me to switch seats with him so he can sit next to his friend, family member, etc., but the switch would put me in a middle seat, is it OK for me to say no?

A: Thanks for not asking about reclining seats. Window-shade-position disputes seem to result in fewer fisticuffs and unscheduled landings. I love to look out the window and hate being told to close the shade. When that happens, usually I compromise by pulling it down halfway. Once a flight attendant reached across me to slam it shut, but I reopened it a bit, and the plane was not diverted to have me arrested. If you are sitting in the aisle and want your seat mate to close the shade, just ask nicely: “Would you mind putting the shade down? And if you do mind, please ignore my request.” As for moving seats to accommodate people traveling together, it’s kind but optional. (I do it for others and have always appreciated when others have done it for me.) The key to this request is the move has to be to an equivalent seat. That means, if you’re asked to move from an aisle to a middle, feel free to decline.

Q. Twin Trickery: I have an identical twin brother. “Liam” and I are professionals in our late 20s who grew up together, attended the same university, and now live in the same metropolitan city working in closely related fields. Ten years ago, when Liam and I were both college freshmen, I made a huge mistake. At the time, Liam had a new girlfriend. Liam, “Jane,” and I went to a party together and drank excessively. Jane and I ended up having sex. Because of our high intoxication levels, I’m not entirely sure if she knew it was me or if she thought I was Liam, but we have never discussed the incident. Jane and Liam are still dating, so she’s a big part of my life. I’ve buried feelings of crippling guilt over the years but it’s becoming harder and harder to cope. How do I overcome feeling like a horrible brother and kind of a creep?

A: When people are really drunk they have a propensity to harm themselves and others—they fall off buildings, they drive into other cars. You had sex with Jane. That did no permanent damage, so be grateful if that’s the worst outcome of your youthful overindulgence. You don’t know what Jane knows, but for the past decade she’s acted as if nothing happened. That sounds like a long overdue strategy for you to adopt. It’s way past time for you to draw the curtain over an episode that should have been lost to your conscious awareness and relegated to a vague, alcohol-induced haze. If you continue to obsess over this, seek short-term therapy to talk this out and help relieve you of the ill-founded notion that you’re the evil twin.

Q. Impressing at Work: I work part time in a research lab at my school and have for three years. The summer has been a challenging time for me, and my contributions at work have been less in number and quality than previously—or than I would’ve liked. During a meeting with my boss today, he mentioned that he was concerned about my commitment level. My summer issues have largely resolved, leaving me much more able to contribute. Here’s my question: The nature of our lab is such that my boss doesn’t get updates about my daily activities, which have to do with the more mundane tasks of running a research study or staying abreast of the literature. We do meet about once a week. What’s the best way for me to show my boss that I am committed to the project and that I am doing productive work?

A: If you were having personal or medical problems that were keeping you from performing at peak, that is something you should have taken to your boss to explain that you needed accommodation to deal with some pressing private matters. Since you were rebuked, it is not too late to have that conversation and explain that you appreciate now that you should have brought this to his attention earlier. If your issues are resolved, say so, and that you look forward to being back performing at your usual level. Then the real solution is to do productive work. After you get back in the swing—say for the next month to six weeks—address this at a subsequent review session. Tick off some of your accomplishments and say you hope it’s clear that you are fully committed to making the lab function at the highest level.

Q. Re: Cougar: I don’t see what’s wrong with someone in his mid-20s dating someone 20 years older. If this were a 26-year-old woman dating a 47-year-old man, I doubt this would be considered much of an issue. As for her alcoholism, it is entirely possible that he wasn’t aware of it until late in the relationship, especially if it were casual. Alcoholics are often really good at hiding it.

A: I know many happy couples with large age differences, but I have written often that when there is a gap that is a generation wide, I advise carefully considering the consequences. I would caution a woman in her mid-20s about getting deeply involved with a man in his late 40s with three teenagers. (A fling is something else.) I agree that the young man’s romantic history is not dispositive that he is a bad romantic bet himself. But it is something to keep in mind.

Q. Caught the Klepto Blues: Since I was in my teens, I have been in the habit of stealing small trinkets from almost every store I go to. I’ll typically take small things of little value like makeup, candy, or jewelry. However, over the years I’m sure the collective sum of my acquisitions is worth thousands of dollars. Over the past year or so, I have completely turned over a new leaf and am disgusted by my former self. Should I attempt to repay stores I regularly stole from? Should I donate a generous sum to charity? I am dumbfounded on how to right my wrongs. Sometimes I wish I had been caught so I would have had real consequences.

A: I wish you had elucidated how you managed this remarkable transition. However you did it, congratulations for recognizing you had a problem and making a change. There is no way for you to go around and repay stores for long-ago stolen lipsticks and Twizzlers. But I agree that finding another way to atone is useful for both the person who committed a violation and for society. Contributing to a charity is one way to do this. You could also do something more hands-on—say donate your time to a group that works with people who need guidance and a second chance.

Q. Re: Cougar: Please can we lose this term? It is sexist and implies that women with a sex drive are somehow predatory or unusual. How about just “47-year-old woman” and skip the judgmental phrase?

A: Good point. 

Click here to read Part 2 of this week’s chat.

Discuss this column with Emily Yoffe on her Facebook page.