Our advice columnists have heard it all over the years. Each Sunday, we dive into the Dear Prudie archives and share a selection of classic letters with our readers. Join Slate Plus for even more advice columns—your first month is only $1.
My boyfriend has always been terrible at giving gifts. For our eight-year anniversary I gave him lots of hints that I wanted something special. In all the previous years he gave nothing. This year he said he got me something meaningful and stupidly I got my hopes up. On our anniversary day, he gave me his—wait for it—wisdom tooth. He had to have it extracted a few weeks earlier and kept it so he could give me a “part of himself.” I’m upset beyond words. How do I teach an otherwise wonderful man how to give good gifts, without specifying exactly what I want?
There is a list of traditional gifts for anniversaries: 1st year, paper; 25th year, silver. But I missed your boyfriend’s innovation: 8th year, enamel! But the thing about giving an enamel gift one grew in one’s mouth is that it should guarantee that the recipient doesn’t hang in there long enough to get the 9th anniversary gift of a rectal polyp. I have long defended people who are bad at gifts or don’t remember anniversaries because I’m one of them. (One of the things that binds my husband and me is that we can never remember when we got married.) But your boyfriend has me rethinking this. He’s not an absent-minded but well-meaning goofball. This gift was crude and deliberate. Maybe he got a laugh when you opened the box and reacted in horror. You say he’s another one in a long line of “wonderful, but” people. I acknowledge there are far worse things than being a lousy gift-giver, and if his other qualities make up for it, so be it. But if after eight years, he wants to mark your togetherness by giving you something his dentist would otherwise dispose of in the biomedical waste bin, he better be really worth it. —Emily Yoffe
From: “Help! My Boyfriend Gave Me the Worst Gift of All Time for Our Anniversary.” (Apr. 14, 2014)
When I was 18, my mom remarried a guy with a son my age. My stepbrother and I didn’t know each other well back then, but after returning from college, I’ve realized that I have a huge crush on him. He’s single, funny, mensch-y, smart, and very good-looking. I think he feels the same way about me, and we totally flirt. If he weren’t my stepbrother, I would definitely ask him out, but I see that there are infinite potential problems here. First off, if we break up it will be insanely awkward, but it’s also kind of weird and incestuous. (On the flip side, we’ve barely known each other five years, so he’s not REALLY like my brother.) Prudie, please tell me not to date my stepbrother so I don’t keep thinking about it!
I can’t quite honor your request to issue a firm nolle prosequi, but I do think you should approach the prospect of dating your stepbrother with extreme caution. As you point out, if things don’t work out between the two of you, it will certainly complicate your family get-togethers. That said, there’s nothing inherently wrong with your feelings for him. You’ve never lived together, you weren’t raised together—in no way is this situation incestuous. Unusual, maybe, but not incestuous. Certainly no worse (and perhaps even slightly better) than Cher and Josh in Clueless. It’s not quite clear if you’ve moved back into your mother’s house (“returning from college” is a little vague). If you have, you should certainly wait until you live on your own to pursue anything. It’s one thing to date an adult stepbrother; it’s quite another to date him in your childhood home, with your mother and stepfather in the next room. —Danny M. Lavery
From: “Help! I’m in Love With My Stepbrother.” (June 13, 2016)
My partner and I have a child together as a result of mixing our sperm before insemination. Before our surrogate became pregnant we decided we would never try to find out who the biological father is, except for serious medical reasons. About a year ago curiosity got the better of me and I got a paternity test done on the sly. It stated I wasn’t the biological father, so I figured my partner must be. I planned on taking this secret to my grave. Then recently I found out our son’s blood type is A. This is impossible because I know both my partner and the egg donor are type B. I am seriously troubled by this revelation because it could mean either the fertility clinic botched up, or the surrogate became pregnant from sexual activity and gave us her own biological child. I need to find out what happened, but it means confessing to my partner I broke a serious agreement. Help.
You and your partner agreed that the paternity of your child would remain a secret unless there were a compelling medical reason. Your curiosity is not a compelling medical reason. There was always a 50/50 chance for either of you that you wouldn’t be the father. It turns out neither of you are. (Keep in mind there is also a chance you have been misinformed about the blood types of the people involved.) I assume that you don’t want to be like the woman in Ohio, who is part of a white, same-sex couple now suing the fertility clinic because their daughter—whom they say they love—turned out to biracial. I assume you both adore your son, so I don’t know what the purpose is of this information. Presumably you don’t want to hand him back to the surrogate and say, “Sorry, we took him by accident—he’s yours.” You violated a trust, and like many people who gather information when they are not supposed to (Prometheus, Pandora, Eve), you have found out there are consequences. I think your consequence is that you do your best to forget this and just be grateful you and your partner are parents of a delightful boy. —EY
From: “Help! I Found Out Our Son by Surrogate Isn’t Our Biological Child. What Gives?” (Oct. 14, 2014)
Eight years ago I had a prolonged affair with a co-worker that ended my already-deteriorating marriage. My ex-wife and I have two teenage boys who don’t yet know the affair was what brought down the final curtain on our relationship. Although my marriage was already on the rocks, I regret having an affair and realize it was the wrong way to deal with my unhappiness. I ended it, we finalized our divorce, and now my ex-wife and I have an amicable, cooperative co-parenting relationship.
Since then, I have tried dating, but have had trouble meeting anyone I care about as much as the woman I had an affair with. I am still in love with her. She now lives far away and works elsewhere, but we have reconnected, and I would love to be in a relationship with her, if it weren’t for our past and the complications it might raise for my relationship with my family. (She feels the same mix of excitement and trepidation.) We have discussed ways to see each other occasionally for now, with an eye toward eventually moving to the same place and being together. The issue that concerns me now is my relationship with my ex-wife and our children. While I don’t think either my ex or I should have any veto over each other’s romantic life, our cooperative co-parenting would be in for a bumpy ride if I were to reconnect with, and marry, this woman. I do not believe that I am entitled to keep the information about how I came to know her from my children, and I know it could be harmful to my relationship with my kids. Do you believe I should pursue this in order to be happy? Or should I avoid it, in order to preserve peace?
This is hands down the most thoughtful, empathetic letter I have ever received from someone who is contemplating renewing a relationship with someone they once had an affair with. “Congratulations” seems like an odd response, but I do commend you for acknowledging your past wrongs and trying to move slowly and to anticipate all future emotional complications should you decide to get back together with this woman. I think you should (cautiously and carefully) reconnect with her. Your marriage is long over, a significant amount of time has passed since the affair, and you’ve tried to date others but haven’t been able to put her out of your mind. Your instinct to prioritize your children’s well-being and your amicable relationship with your ex-wife is a good one, and while there will be challenges, they should not be enough to prevent you from moving forward.
First discuss with your wife the prospect that you may be renewing your relationship with this woman, and reaffirm your commitment to raising your children together, making it clear that you’re not looking to move her into your house next week. The two of you should decide together how, and to what extent, you will tell your children the truth without going into the gory details of the end of your marriage. They already know that your marriage is over, and they’re nearing adult age, so you’ll have to decide what information you think they’re ready for and what would not be helpful for them to know yet. It may prove more difficult than you anticipated—even the most amicable of ex-spouses will feel bitterness about the situation you’re presenting her with. It’s possible that couples counseling with your ex might help you both figure out how to navigate this tricky situation as honestly and as openly as possible—just because you’re divorced doesn’t mean you aren’t partners in a very real way. Good luck. —DL
From: “Help! How Do I Tell My Ex-Wife and Kids I Want to Be With the Woman I Had an Affair With?” (Dec. 1, 2016)
More from Dear Prudence
I was barely an AA cup as a young woman and very self-conscious about it. At age 36, after I finished nursing my youngest, I had breast augmentation surgery. For the past 10 years I’ve been a B cup, and I’ve been completely satisfied with my decision. My daughter, who’s about to turn 18, has inherited her breast size from me. Although we haven’t talked about it explicitly, I suspect she’s just as self-conscious about it as I was. She has literally run away to hide while I consulted with the lingerie sales lady about bras for her. I’m thinking about offering her the option of augmentation surgery before she goes to college. She doesn’t know I have implants, and we’re not generally an image-centric or pro–plastic surgery kind of family. But I’m worried that if I suggest this, I might create the very self-consciousness that I’m aiming to help her relieve. I don’t want her to think that I think there’s anything wrong with her body. Is this a terrible idea? And if I’m not crazy, how do I bring this up in a way that doesn’t imply that I think there’s something wrong with her?
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