Dear Prudence

Nothing but a Number?

Prudie advises a letter writer whose 66-year-old mother is moving in with her hot 30-year-old boyfriend.

Daniel Mallory Ortberg, 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

Q. Mama’s boy!: My mom is 66 years old and has never been married or dated very much. She’s not rich and looks good for her age, but not unusually so. Last month, she told me her boyfriend was moving in with her, and this weekend I met him. Prudie, he’s my age (31), devastatingly handsome, nice, and seemingly intelligent. I’m totally baffled. My mom seems head over heels for him, and as far as I can tell, he reciprocates. I don’t even want to think about why my mom and this 30-year-old hottie are dating, but should I meddle or leave her alone? A part of me worries she’s being scammed in some elaborate way, and another part is just reeling. Advice would be much appreciated!

A: I understand the surprise, as it’s an awfully large age gap, but your mother is only in her mid-60s and seems to be in perfect command of her faculties—it’s a little soon to fear “elder abuse,” especially when men in their 60s appear to regularly fall prey to hot thirtysomethings without anyone worrying about their well-being. You don’t say anything aside from this man’s age or appearance (is he borrowing money? Does he treat her with respect? Is he trying to isolate her from her usual friends or hobbies?) that suggest he’s taking advantage of her. Until you have evidence to the contrary, I think you should treat your mother’s new boyfriend as just that: your mother’s new boyfriend, not some grifter with a Cocoon fixation. She’s barely reached retirement age; it’s not as if she’s about to be consigned to a nursing home. That doesn’t mean you have to embrace him uncritically—by all means, trust but verify. If he starts treating your mother in a way that suggests a potential for abuse, you should absolutely intervene, but there’s a non-zero chance that he’s just happily dating an older woman. (It happens! No need for bafflement!)

Q. Equal measure: My husband and I are retiring this year and selling off an old beach house we bought years ago. We want to split the profits with our daughter and granddaughter. We have given our sons a lot help over the years—over $50,000 for several failed businesses to one and bought a condo for the other. Neither my daughter nor granddaughter got anything from us other than a used car when my granddaughter finished her tour in the Air Force.

I feel that letting my daughter pay off her home and my granddaughter potentially buy her first is both just and fair. My husband is worried about upsetting our boys. Well, they got theirs first. He thinks we should just not tell them about the sale and give the girls the money secretly. I don’t think secrets like that stay secrets long, plus we are doing nothing wrong anymore than 10 years ago when we gave them the money for the condo and business. We need an outside perspective.

A: Why on earth should you do secretly for your daughter what you once did openly for your sons? They’ve gotten money and help buying a home from you in the past; now you’re doing the same thing for their sister. If their response is anything other than pleasant and supportive, the problem is theirs, not yours.

Q. Moving from romantic partner to buddy: I was thrilled a little over a year ago when I met a lovely man who was funny, sweet, thoughtful, active, and adventurous. We’ve spent nearly every weekend together surfing, hiking, mountain biking, kayaking, you name it; have enjoyed monthly getaway weekends; and get along beautifully in all respects. He helped me train for my first triathlon last summer and cheered when I reached the finish line. He makes everything interesting and fun. He’s my best friend, and he says I am his. Because his work takes him all over the state, we rarely see each other during the week. But it’s allowed me the space I need to settle into the relationship on my own terms and at my own pace, and I’ve been careful not to repeat mistakes I’ve made in past relationships, such as bonding too quickly with a man only to learn over time we were not a good fit as long-term partners.

As we approached the one-year mark, I realized I wanted to invest in our relationship for the long haul. When I shared my feelings with him he confessed that while he loved me he did not see me as a life partner. He said that our age difference—my mid-50s to his early 40s—had prevented him from thinking in those terms from the beginning. He is holding out for a younger woman with whom he can have a family. Of course I’m disappointed, but we had made no promises, and I hope he can create the life he’s envisioned. However, he continues to refer to me as his girlfriend to friends and co-workers, and we function as a couple, so I’m confused about how to assimilate this new information. I’m feeling ambivalent and unsure of how to think of “us” now. I don’t want us to continue to be romantic/sexual partners, but I also don’t want to sacrifice the emotional intimacy we share. What are we now? Besties? Buddies? I can live with that, and I’ve accepted the likelihood that sooner or later one of us will meet someone better suited as a long-term partner. But he clearly wants to continue with all the trappings of a legit relationship, and he says he’s happy. What’s going on here?

A: I think it’s fairly clear what’s going on here: Your boyfriend is happy with you now, but he wants to have a family someday and considers your age gap insurmountable in the long run. In the absence of someone he sees as a likelier long-term prospect, he wants to continue things as they are now—you’re dating with an expiration date. The question now is whether or not that could make you happy. If you think you can honestly enjoy the rest of your time together without looking over your shoulder, afraid of every fertile thirtysomething in kayaking distance, then by all means, continue seeing him. Not all good relationships last forever, and I don’t think either one of you is doing anything wrong. But—and it sounds like this is more likely the case—if continuing to date him under these conditions would make you feel anxious about the future and shunted-aside, I think you should end things, even if it means sacrificing the emotional intimacy you share now. I can’t imagine he’s going to have time for two-day mountain-biking trips with you once he starts seeing someone else that he wants to start a family with, and you should prepare yourself for a more distant friendship with him than the one you share now. What you’re hoping for—a breakup that sacrifices none of your current emotional closeness and doesn’t require either of you to prioritize the other any less—is awfully rare, and in your case, I think, impossible. Better to end things and mourn it all now than try to spin a romantic relationship into a best friendship and watch yourself decrease in importance in your ex’s life.

Q. Bed & breakfast: My new boyfriend and I are moving in together. He’s an exceptional guy, very rational and planned, and asked me to move in pretty quickly. I said I would if he’d move out of his studio into a bigger apartment. I found him one that’s not more expensive than his old one. We have many disagreements on how much stuff to keep (I have many clothes, shoes, etc.), but the biggest disagreement is whose mattress to keep. I’ve been trying to argue that mine was much more expensive and is higher quality, but he insists that his $200 memory foam one is the best. I hate it. What to do?

A: Use your fancy mattress, and buy one of those $30 memory foam toppers they sell at Bed Bath & Beyond. Mattresses are no small matter! It’s unbearable to try to fall asleep every night on a surface you really can’t stand. If he won’t accept that compromise (and you can afford it), go shopping for a mattress together and find one you both like, like in those commercials where one partner pantomimes flinging herself about on her half of the bed, while the other sleeps like the dead. Simplest of all, however: Don’t move in with him yet; wait until you know one another better and have figured out how to fight a little more constructively together.

Q. Misspellings: I have a friend who consistently misspells my name on texts and social media. (It’s written out right there!) I have a simple, four-letter name, of which they invert two of the letters. I have known this person for about four years, and while we’re not particularly close, it’s still a tiny thorn in my side every time I see my name misspelled. I always assumed that they would notice at some point on Facebook, so I’ve let it go on for far too long. Do I say something? Do I let it keep bugging me?

A: Oh my God, say something! You do not need my permission to tell your friends if they are spelling your name incorrectly, but you have it nonetheless. Why on earth would you just let this continue? A simple “Hey, it’s actually spelled T-R-O-Y, not T-O-R-Y” (or equivalent) will more than fit the bill. Surely you’d hate to learn you’d been misspelling one of your friend’s names for years; offer a friendly correction and don’t force yourself to answer to S-A-E-N instead of S-E-A-N (I feel I’m not guessing your actual name, and for some reason this bothers me) just because you worry about coming across like a diva by asking that people spell your name correctly.

Q. Long time no remember: This morning my work email brought a message from a woman I haven’t seen in more than five years. We worked together (different departments, same university) in early 2011. At first I thought the email was a mistake—meant for someone else with my name—because I didn’t recognize the sender’s name. But then I remembered her. She and I had lunch or dinner together a couple of times when I lived in that city, and we talked about work stuff; both of us were from someplace else and neither had many friends there. It wasn’t what I would call a friendship. Her email says that she is coming to my current city for a particular art exhibit and that she would like to see me (maybe catch the art show together), and asked whether I would be interested in meeting when she’s here. I’m not. I remember so little about her. After all this time, do I owe her a reply? In fairness to her, I probably said something like, “If you ever come to [my city], let me know.” It would be like me to issue such an invitation never thinking she’d take me up on it. Why do I feel guilty for not wanting to reconnect?

A: I have no idea why you feel guilty about it, but there’s nothing wrong with not going to museums with old co-workers. I don’t go to museums with former co-workers all the time, and look forward to a rich future of avoiding trips to the museum with old co-workers for years to come. There’s no reason for you not to reply to her (eminently reasonable!) request, however. You don’t have to ghost on her; you can simply tell her you can’t make it. This is the sort of situation the polite lie was made for: “Oh, you’re coming into town the week of the 20th? I’m afraid I’m busy that week. Have a great time at the show, and thanks for thinking of me.”

Q. Gift horse: I love giving gifts. I travel a lot and am constantly on the look out for unique, personal items that I know will mean something special to my friends and family. It’s a kind of sport for me, I guess, but I never thought about its having winners and losers until this last Christmas. I have a friend of 20 years who’s been married these last four. I usually get her something special and give him a bottle of Scotch. While I don’t know him that well I do know he collects a very specific type of sports memorabilia and while traveling last year I found a very rare and underpriced item that I knew he’d been searching for. So I bought it for him and waited eagerly for Christmas. But the moment he opened it I knew I’d made a mistake. He was overjoyed and declared it the best gift he’d ever gotten, and my friend was livid. She dragged me into the kitchen and tore me a new one. She was furious that I’d give her husband such a personal gift. I was shocked, but I also understood her anger when I realize I’d totally upstaged her in the gift-giving department (she’d given her husband a new phone). I apologized profusely and told her it was a mistake. The problem is now, six months later, she’s still mad at me. I don’t know how much her husband knows, but he’s been really awkward around me since then. I already apologized once. I don’t know what else to do.

A: Nothing! Your friend is being churlish. It’s one thing to object to a highly personal gift (I think what you did was lovely, by the way) given to one’s spouse by a mutual friend, but it’s nothing to get “livid” over, and certainly nothing to hold onto for the next six months. Does she think you have sinister designs on her husband and have chosen the medium of sports memorabilia to transfer his affections away from her and toward yourself? Your gift was thoughtful and unique, but it’s not as if you bought him a new car, or something highly personal and inappropriate, or even particularly expensive. You’ve known her for a long time, so I think your relationship can handle a frank conversation: Tell her you’re sorry that you upstaged her in the gift-giving department, but that she’s never complained about your thoughtful presents in the past when she’s been the recipient, and that you’re not trying to steal her husband away via, I don’t know, a football phone, and that she needs to stop punishing you for such a minor transgression. I, by the way, don’t understand her anger; I’ve been perfectly happy to see romantic partners get thoughtful gifts from other people. It’s clear from your letter that you and her husband have never given her reason to feel jealous, and that you’ve never used gift-giving to manipulate others or to pit couples against one another, so her reaction is in especially bad form.

Daniel Mallory Ortberg: Goodbye for now, everyone, and remember to go kayaking with the people you love, for as long as your heart and arms can bear it.

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