Dear Prudence

The Comeback

Prudie counsels a letter writer who broke up with a fiancé six years ago—and now wants him back.

Emily Yoffe.
Emily Yoffe

Photo by Teresa Castracane.

Emily Yoffe, aka Dear Prudence, is online weekly to chat live with readers. This week, due to technical difficulties, Prudie responded to submitted questions offline. The edited write-up 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

Q. Old Flames Die Hard: Six years ago I broke up with my fiancé because I felt like we were no longer happy together and he never made time for me with a demanding job. I was confident in the decision, and while he was incredibly upset, he assented to the breakup. Now, at age 40, and after dating numerous other men, I realize that this breakup was a mistake. He made me much happier than any other partner has since, and I just didn’t realize a good thing when I had it. We don’t really speak much anymore, but I want to make contact to see if we could rekindle what we had. I’m hopeful I could persuade him that I made a mistake and he was right all along, but that may be unrealistic. Am I making a mistake trying this? Should I just give up on this man without a fight?

A: It sounds as if you gave him a pretty good fight six years ago when you confidently said you were done. Your letter is a cautionary tale for people who feel they are with the right person but who have to work out some difficult compromises. You learned over six hard years that everyone else was more flawed than your Mr. Wonderful (retrospective version). There’s nothing wrong with trying for your relationship, 2.0, but since you’ve been in only sporadic touch in the past few years, you have no idea where he’s at. Go ahead and reach out, but be much more restrained with your information than you are here. Don’t say you washed out at finding a replacement and you now realize what a dope you were and you want him back. Instead, say you’ve been thinking about him and missing him, and wondering if he would like to have dinner. It could be that when you’re face to face again, you’ll realize why he’s out of your life.

Q. Blended-Family Turmoil!: My 7-year-old stepson cries uncontrollably every week when pickup time with his mom rolls around. His mom and I sat down and agreed to trade family pictures so that he had a picture of each family at the other home. My stepson told me the other day that he went to get his picture, which his mom makes him keep in a drawer (her family’s picture is displayed in our living room in a frame) and it was gone. He said he later found it torn up in the trash in the bathroom. I think it’s sad that this happened, but can’t tell them how to run things in their home. My stepson gets in trouble every week for crying that he doesn’t want to go. But I fear it’s a vicious cycle. If they are so hard on him, he will naturally pull away.

A: I’m assuming you’re the stepmother, so I hope your stepson’s father is paying attention to what’s going on. This little boy is 7 years old, and transitions are hard for lots of people, especially elementary-school-age children who bounce between homes. But if he’s being punished and psychologically pressured over having a good and happy relationship with his father and stepmother, that’s deeply concerning. It might help to get the boy a therapist so he can talk about what’s going on in his life and so his father can be on top of what’s going on. What’s crucial is that you and his father keep this connection strong. Your stepson needs it.

Q. Lost Friend: I have been a friend with someone of the opposite gender for close to 15 years. She’s married, and I am in a serious relationship. I hadn’t heard from her for about two months, so I called and left a message just calling to say hi about three weeks ago. I didn’t receive a call or text back, so I called and left a message this past week asking if everything was OK. This morning she called and told me not call her again, that our relationship was inappropriate, and she apologized for this coming out of the blue. I am at a complete loss and I don’t recall doing anything to offend her, and she didn’t really supply any reason for this sudden rupture. Is this one of those growing-up lessons and I should just let things go? Or should I shoot her an email or text and asking her what’s up? I feel like that would go against her wishes of not contacting her. My S.O. has offered to call her to check in and see what’s up (they’re friends too), but I feel that that’s weird. What’s a guy to do?

A: This is sad and distressing, and I agree that a 15-year friendship deserves better than this. I’m concerned that she was forced to do this by her husband—you don’t say how long she’s been married, but however long it is, maybe he’s found your friendship to be a source of jealousy and insecurity and he’s finally forced the issue. She has told you that she doesn’t want to contact her again. I’m afraid you have to respect this request. Let’s hope someday she’s able to reconnect, and explain what was going on. And let’s hope that she’s not under the thumb of a control freak.

Q. Three Dads?: I was the result of a hook-up. My parents never pursued a romantic relationship, but I get along with both of them swimmingly. When I was 2, my mother married “Larry.” Larry had a huge impact on my formative years and he means a lot to me. A year ago he reached out to me and we have been in contact ever since. We go out for coffee or lunch at least once a month and exchange text messages regularly. I treasure our friendship. My mother, who is no longer married to Larry, finds our friendship bizarre. She says I already have two great father figures (my father and current stepfather). Am I wrong for pursuing this friendship?

A: How sad that your mother would like you to have less love in your life. How wonderful that Larry, who was an important father figure to you, has renewed that “claim” now that you’re an adult (I’m assuming) and are free to make your own relationships. Your mother had her own reasons for severing her ties to Larry, but she should be big enough not to interfere with your delightful reacquaintance with him. The easiest thing is for you to stop updating her about this. She doesn’t want Larry in her life; you want him in yours. There’s no need to keep her updated on your lunch activities.

Q. Wedding Invite: A close friend has just sent me a save-the-date for his fourth wedding. I sigh because if I go to this one, I will have attended three of his weddings, complete with expensive gifts. He has dated this one for all of two months, and I suspect that he is off his meds for bipolar. Do I really have to go?

A: Since you two are close, you should have a conversation with him about your concerns. You could also reach out to his parents (if they’re in the picture), siblings, or people who might be able to persuade your friend to get to a doctor, fast. No, you don’t have to pretend that this apparently dangerous manic episode is a happy event.

Q. No Harm (to Me), No Foul?: I am in my early 30s and newly married to a great and trustworthy (I thought!) man. He recently came home limping from a soccer game after taking the ball to his … jewels. He casually mentioned that the injury may have ruptured his testicular cyst. He then revealed that before we met he discovered a cyst and was told it could make conception difficult. I am currently three months pregnant. It took us about five months to conceive. I admit I was impatient but I found the wait frustrating and confusing. He said he didn’t tell me about the cyst because it was personal and since I was so anxious about getting pregnant he didn’t want to make it worse. Isn’t this information one discloses pre-nuptials? Does this reveal a deeper problem with honesty? Or do I just let the ball lie where it fell?

A: So a ball to the balls may have resolved his cyst—talk about sports medicine! I agree that before entering into a marriage, the two parties should disclose their medical conditions to each other—especially if there is a condition that could affect conception. I hope, however, that you are not saying that had you known, you would have rethought your marriage because of a sack of fluid in his sack. Surely you know that getting pregnant after five months of trying is a quick and happy result. That you describe yourself as being impatient, frustrated, and confused leads me to believe that your husband simply made a calculated decision not to increase your already significant anxiety. And everything turned out fine! I think this is a good opening for the two of you to have a discussion about how you both deal with the tough things that are an inevitable part of life. If your husband withholds because he doesn’t want to deal with your reactions, then this is a matter of how you interact as a couple, not just that he thought “nuts” to telling you about his nuts.

Q. Sixth-Grade Teacher Insists Students Address Her as “Doctor”: My daughter’s sixth-grade English class has a new teacher. I haven’t met her, but her introductory note to parents dwelled on her Ed.D., which she completed five years ago after several decades in education. She signed it formally: “Doctor Anita Horgarth.” The class has not warmed up to her, and my daughter now tells me her teacher has been ignoring students who call her “Ms. Horgarth”—she will only respond to students who address her as “Dr. Horgarth.” I’ve told my daughter this is both silly and sad. Should I explain she should just learn to accommodate fools who might otherwise make life difficult? Or should I suggest she refuse to answer her teacher unless addressed formally as “Reverend Miss Maizy Russell,” as my daughter has the privilege, despite her youth, of being ordained in the Church of the Flying Spaghetti Monster?

A: If this woman is a lousy, punitive teacher, that should be brought to the attention of the principal. The issue is not her sense of entitlement about her title (and I agree it’s silly). The issue is her teaching skills. If indeed they are lacking, it would help if you went with two or three other parents who have similar concerns. In the meantime, this is a good lesson for your daughter about getting along with difficult people, because Dr. Horgarth is not the only pompous person she will encounter. It’s an easy gimme for her to say “Dr. Horgarth.” Of course your daughter is free to think of her teacher as Anita Horgarth, Ed.D., P.F.—pretentious fool. But maybe there are also good things about this woman. If so, another good lesson for your daughter is accepting that everyone has flaws and it’s worth overlooking the easily overlooked ones.

Q. Pregnant but Not As Excited As They Want Me to Be: I have recently disclosed to my co-workers that I am pregnant, less than a month after marrying my husband. I have never had an over-the-moon desire to have children—but my husband very much did, and we compromised at having one. I will love this child more than life and be the best mother I can be—but I’m not really excited about being pregnant or being a mother. There are several women who tried for years to have children, including rounds of fertility treatments and eventual adoption. They are beyond excited for me. They want me to be glowing every day and share the joys of being pregnant. How do I not sound totally insensitive when they ask me how excited I am about being pregnant? If it was just once, I would suck it up and lie, but I see these women every day.

A: You are in your first trimester, so that gives you an easy out for your lack of glowing ecstasy. “I’m so happy, thanks. I’ll be even happier once I can keep down my breakfast.” One recurrent issue I hear from office workers is the pressure they feel to discuss issues that aren’t in any way related to work: their religious beliefs, their conception issues, their relationships with their spouses, etc. You need a way to politely push this off in general so that you get along with your co-workers while establishing there are things you don’t discuss in depth with them. It will be good to establish some boundaries now, so after the baby is born your entire workday is not consumed with discussions of breast-feeding, sleeping through the night, and toilet training.

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