Dear Prudence

Degree of Difficulty

Prudie advises a letter writer whose fiancé is embarrassed about not having gone to college.

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 here 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. Let’s get started. 

Q. Educational Differences: I am engaged to a wonderful, funny, intelligent man, who, as we approach our wedding date, will be meeting more of my extended family and friends. I graduated from a prestigious university, and my family and friends usually assume that we either met there, or that he attended another notable school. However, he got his GED after dropping out of high school, and it embarrasses him when people ask where he went to college. He has a successful career, his lack of degree has never been an issue for us, and we know people only ask to make conversation, but it still makes him uncomfortable every time the question comes up. What is the best way to respond to spare him (and the asker) embarrassment?

A: There are lots of successful people who just weren’t cut out for school—Richard Branson, for one. Sure, dropping out of high school is not the usual path to becoming a billionaire, but your guy has made a success of himself without academic credentials. It’s too bad he’s insecure about this. He needs to embrace his unique path and also put others at ease when they make small talk. You can help him. Tell him you know this comes up all the time and he shouldn’t feel self-conscious. When asked where he went to college, suggest he smile and say, “I didn’t. Heather and I met at a conference.” That way he will deflect the awkwardness and express his own comfort with his choices. 

Q. Salacious Selfie: I am an early-30s professional woman in a junior executive position at an ad agency. I am also in a long-distance relationship, so I send and receive explicit photos with my significant other (yes, I know it’s risky). I keep these in a vault app on my phone that requires a password. Last week we had a company party and I asked our early-20s marketing assistant (female) to take a picture of me with a co-worker and realized that a suggestive, but fully clothed photo was in the thumbnail of the camera function. She seemed confused about how to use the phone camera and passed it back to me. I snapped a photo of the ground and gave the phone back. Should I just pretend like nothing happened or do I acknowledge this with an apology, although the photo may not have even registered for her?

A: Anything you say will be so much weirder than anything she saw: “You know that picture of me with my lips parted, cupping my breasts? I did that because my boyfriend and I live far apart, so we send each other sexy selfies to masturbate to.” It’s likely the assistant didn’t see anything, and since you were dressed in the photo, there doesn’t sound like anything to see. Since you have acknowledged the risk of such pictures, however, let me pick up on that. Sure, you have them stored in an electronic vault. And sure, you love your boyfriend, and he would never do anything to hurt you. Except that when people break up, sometimes they hurt each other. In an era when people took sexy nude Polaroids of themselves and stuck them in the sock drawer, there wasn’t much to worry about. Now, with the tap of a finger, your private parts can instantly been seen by strangers from Bosnia to Bimini. You’re not Jennifer Lawrence, so hackers are probably not trying to break into your vault. And I hope you and your beloved go on to a life of happiness. But instead of keeping each other excited with sexy images, maybe you should shift your focus to old-fashioned dirty talk.

Q. Re: Educational Differences: I was in the same boat. I dropped out of college and it surprised people because I’m intelligent and well-spoken. And I was incredibly embarrassed by it, whether or not I had any reason to be. So … I went back to school. Got my degree, and now I can answer the question without the least bit of shame. If it really bothers him, maybe he should think about doing the same. (Especially if his employer does tuition reimbursement!) My degree increased my marketability and earnings potential, of course, but the self-satisfaction was probably worth more than the rest all put together.

A: That’s another great point. These days, there are so many more ways to get degrees. He could likely enroll at an accredited university with an online program that would probably give him considerable credit for his life experiences. And if his employer was willing to help with tuition, getting his degree would deal with his insecurity about this and maybe make him more marketable down the road. 

Q. Re: Educational Differences: “I went to school in Boston.”

A: Nice one! Thanks.

Q. Dating an Underage Woman?: I’m a 26-year-old man attracted to a 17-year-old woman. I don’t assume traditional social conventions to be right, but is it possible to break this one? This woman started pursuing me—I’m not an aggressive person in general compared to most men. I’m elated when I’m with her. We go to the same college, we are both ballet dancers, and have similar dispositions. We share a lot in common, except our age. Is it possible to ethically and healthily have a relationship with this age gap, or does my age make this impossible? Would this inevitably cause a power imbalance? 

A: Lots of couples have such an age gap, but your issue is your ages at which this gap is appearing. She’s in college so presumably she will turn 18 soon. So wait until this magic now-she’s-a-legal-adult age happens before pursuing anything romantically. After that, you two can follow your hearts. Since she’s the one who’s pursued you, she sounds like a young woman who will keep you on your toes.

Q. Pajamas Outside?: Please settle a debate! I live on a back road, so only neighbors and such are around. Is it OK to go outside, briefly, in pajamas? I mean, running out to the car, grabbing the mail, or smoking a cigarette. The pajamas aren’t at all revealing—just loose pants and a baggy shirt. My boobs are fairly small (thank you surgery!) so it’s not obvious that I only have a shirt on; I’m not at all worried about any attack, since it’s a very safe neighborhood and I’m trained in self-defense. This debate is about propriety.

A: Walk around any major downtown and see what people are wearing (or not) and you will feel as if you’re in a burka in your pajamas. Presumably someone you love is telling you to get fully dressed before you step outside. But loose flannel pants and shirts are fully dressed when it comes to getting the mail, etc. It’s not even a bathrobe! (I’m on a Jim Gaffigan quoting jag, and I love his line about the inventor of the bathrobe saying, “I’ve got an idea, let’s make a coat out of a towel!”) You say you’re trained in self-defense, so train some of these defenses on whomever is telling you to put on a business suit when you go outside to have a smoke.

Q. Re: Educational Differences: If he’s successful now without the degree, it’s not going to make him any more marketable to have a bachelor’s degree. My husband completed only a year of college before dropping out and he has been wildly successful without the degree. What started out as a hobby became his career and if he were to go back to school now, he’d probably be able to teach the classes. If I were the LW’s husband, I’d be thrilled that I became successful and didn’t have to go into debt for school to do it.

A: Becoming wildly successful is its own reward. And it sounds as if your husband is an entrepreneur with his own business. I agree if someone is on a great trajectory without the degree, be comfortable with that. But if the letter writer’s boyfriend is uncomfortable, or down the road he may be stymied at getting jobs because they require a degree (no matter how irrelevant that is), he may want to look into getting one. I agree the key is to do it without debt, which he may be able to swing.

Q. Re: Salacious Selfie: Keep in mind that it doesn’t have to be after a breakup for pics to be used. I was working in a large firm a couple of years ago. A guy (older—and old enough to know better) received a reclining nude photo from his girlfriend and set it as his screen saver. Which would have been nobody’s business except that his screen faced his open door. Anyone and everyone saw her … including the night-cleaners!

A: Unless this guy worked at Playboy Enterprises, is he nuts!? Did anyone ever say, “Hey, Dick, I didn’t know you were dating Miss January, and now it’s time that no one knows.” I believe people can memorialize their hotness, they just need to be cool-headed about how they do it. 

Q. An Ex-Friend’s Nasty Divorce: A few years ago a friend of mine and I had a bitter falling out. Since then she has bad-mouthed me all over our gossipy town. She said absolutely brutal and untrue things about me and even fabricated a story about me sleeping my way to the top in my career. It took me quite a few years to bounce back. I don’t claim to be entirely innocent, but I never stopped as low as she did. In the past year, she’s begun one of the nastiest divorces I’ve ever seen, and I have a bit of important information about her soon-to-be-ex’s finances that would benefit her greatly in court (our husbands are co-workers and it has to do with company investments). I’m at absolutely no legal obligation to disclose to her, but am I at a moral one? She has three kids between 5 and 11, and although I don’t care for her, I think it could affect her children.

A: If you help this woman, I assure you that somehow it will backfire on you. She is a dangerously unstable and vindictive person. But she has a lawyer and this professional should be the one to ferret out helpful financial information. It took you years to get over being trashed by this loon, so don’t sign up for another round. 

Q. Passive-Aggressive Lawn Care?: I live in a middle-class suburban neighborhood where most of us mow our own lawns and occasionally go a bit too long between mows. My driveway and those of my next-door neighbors are situated to the far side of our property, so the majority of our grass is in front of the house but there is about a 5-foot strip on the far side of the drive that is essentially attached to the neighbor’s yard. Every time I mow my front yard I wonder whether to include my neighbor’s 5-foot strip when I mow my front lawn. Is it a friendly and neighborly gesture or would it come off as a passive-aggressive way of saying it’s time for them to get mowing? (For the record, I don’t know either of my neighbors very well, other than to wave hello when we’re outside at the same time.)

A: Next time you’re going to mow, ring their bell and ask. You can say when you’re out there it’s really easy for you to do the strip between your two houses, but you don’t want to intrude if they would prefer you didn’t. 

Q. Fond Memories, or Creeper Status?: At the end of my high school career and on my summer breaks in college, I babysat for “Linda” and her three adorable children. On breaks, I would call her when I was back in the area, but unfortunately, during my last year in school, I dropped my phone in water and I couldn’t recover the phone numbers in my phone book. I thought about her family often, but without her number, I haven’t contacted her since. It has been about five years since I last spoke to her, and one day, I Googled her and found her phone number. Is it inappropriate to call her and connect with her? I don’t want to be creepy, and I would probably have to explain why I haven’t called in so long, but I remember them fondly and want to see how the family is doing. What should I do?

A: This isn’t creepy at all—it will probably be delightful for them to hear from you and catch up. But no one talks on the phone these days, so see if you can send a private Facebook message or another way to get back in touch electronically. That way you can exchange photos and see how those adorable kids have grown up. 

Q. Re: Educational Differences: I think the idea of telling this guy to go back to school misses the point. Telling a bunch of private school grads that he went to the University of Phoenix isn’t going to make him feel better about his situation. He needs to realize on his own that college wasn’t for him and that is OK, he didn’t need it. There will always be a few who raise their eyebrows, but you’ll never change that and their opinion really doesn’t matter.

A: I said he should be more comfortable with his lack of degree. Someone else in a similar situation said getting a degree really helped. So if not having a degree really does bother the fiancé of the letter writer, I agreed that today there are many ways for someone like him to get a degree from an accredited university by taking classes online in his own time and getting credit for his work experience. But only if he wants to!

Q. Proper: Is it proper to be asked to change seats in the cinema or plane to allow for a better sitting arrangement for a couple? I have had in recent times two experiences where couples asked me to change my seat because they want to sit together. In both cases, I did change my seat to avoid a scene, but I wonder why as a couple why you would come late to the cinema. And if you want to sit together, then check in online and book preferred seats.

A: You must not fly or go to the movies often. It’s not unusual that by the time you book airplane seats, there are no seats together. I have often asked people if they could make a switch and as I have been asked, and have always been accommodated and accommodated others. The key is that one doesn’t request the mover change to a worse situation. That is, you don’t suggest going from an aisle seat to a middle. But what’s the difference in moving your aisle seat by a couple of rows? Similarly, you can’t always get to the cinema in time to sit together, so if by your moving right or left by one seat, you allow a couple to share a box of popcorn, it’s really petty not to—unless moving puts you behind the patron who’s 6-foot-6. 

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