Dear Prudence

Help! It Turns Out I’m Dating My Ex’s Daughter.

Read what Prudie had to say in Part 1 of this week’s live chat.

An older man in a white T-shirt being embraced from behind by a younger woman.
Photo illustration by Slate. Photo by Nick White/DigitalVision via Getty Images Plus.

Dear Prudence is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat.

Jenée Desmond-Harris: It’s the weird week between Christmas and New Year’s Eve. If anyone is actually online and alert, let me know if you had any holiday drama or if there’s anything else on your mind.

Q. Like mother, like daughter: I am a 50-year-old widower and a friend of mine introduced me to “Susan,” someone she knows who is my age and divorced, thinking we would hit it off. We have gone out a couple of times and it went well, but I had this strange feeling that something was familiar about her. Our mutual friend showed me Susan’s Facebook page and I saw something shocking.

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Years ago when I was in my 20s living in another city, I dated “Jackie,” a woman 30 years my senior. We got along well, but the age difference was too much so we amicably parted ways. She was uncomfortable with others knowing about our relationship, so we agreed never to discuss it with anyone. On Susan’s page was a memorial to Jackie. It turns out Susan is Jackie’s daughter. I’m not sure what to do about this. Should I tell Susan about my past relationship with her mother? Should I wait and tell her later or not tell her at all? It has created an awkward situation and I’m not sure what to do.

A: Awkward, indeed. I would tell her when you get to date No. 5. That’s because you do want to respect the fact that Jackie kept your relationship a secret and wouldn’t want Susan to know. And if you and Susan are going to realize you’re incompatible after a couple more dates, she really doesn’t need access to this information … but if things are going well and getting more serious, you have to choose honesty with the person who is still alive and in your life over the person from your past. Mostly because if your relationship progresses, you don’t want the burden of carrying around this secret.

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How to Get Advice From Prudie:

• Send questions for publication here. (Questions may be edited.)

• Join the live chat Mondays at noon. Submit your questions and comments here before or during the discussion.

Q. Thanks but no tanks: In the nine years I have been with my husband, I never had a good relationship with my brother-in-law. This Christmas, he genuinely wanted to fix that and bought me a snake startup tank with all the things snakes need because he kindly remembered I like snakes (and enjoy holding a friend’s snake when I visit).

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The thing is, I never want to own a snake! I live in a tiny apartment, don’t like pets, and plan on having a child soon, so a snake is out of the question. He is so excited about it, thinks it is the perfect gift, and now everyone is asking me what snake I plan on buying and offering to go with me to a pet store to pick one out. It would break his heart and ruin our relationship (and my relationship with my in-laws, who are so touched by this gift) if I said I never plan on owning a snake and to return the tank.

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What should I do? Keep the tank in my apartment and dodge questions about when I will get one? Try to get pregnant tomorrow and use it as an excuse? Ask my husband to talk to him? I really don’t want to ruin what feels like the start of a good relationship, especially because the gift really IS so kind and thoughtful. But a pet is a HUGE decision, and it would not be fair to the snake (or me) to buy one just to show my appreciation.

A: This is going to be a difficult conversation, but you should tell your brother-in-law the truth. The truth isn’t unkind; it’s not just “I can’t keep this gift, get it out of here.” It includes everything you’ve said about how thoughtful he was and how much you appreciate that, how worried you are about ruining your relationship, and your very real concerns about not having a snake and a baby at the same time. Start and end the conversation by telling him how grateful you are and how you hope this decision won’t affect your relationship with him. But honestly, if the relationship is delicate enough that it can be destroyed by a perfectly reasonable decision not to take responsibility for a pet, it was never really repaired at all.

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Q. Just want to be myself: I’ve been with my boyfriend “Steve” for a while now and love him very much. But Steve’s family is very traditional and very into their holiday stuff. I try my best to just go with the flow but I don’t particularly want to celebrate holidays based on Christianity because I’m the farthest thing from Christian and I just don’t feel all that good about getting gifts and trying to find gifts for everyone. It makes me think about holidays growing up, which were never good. I just want the holidays to be a regular day, and I just think the whole concept of giving gifts because it’s a certain day is yucky. Another issue is that I am a medical cannabis patient and I have to sneak using it around them because they probably wouldn’t like that I use cannabis, even though it’s legal and prescribed.

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So two parts: How do I stop celebrating holidays I don’t want to celebrate, and how do I stop feeling like a teenager sneaking around my boyfriend’s family? Am I just going to have to accept that being myself means they don’t like me, and hope they can be civil?

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A: When it comes to the Christmas issue, my first reaction is to say that there is ONE Christian gift-giving holiday per year, and this seems like something you could probably just suck up (maybe with the help of therapy to try to turn down the intensity of your childhood memories and reframe how you think about participating in this tradition). But, you know, if you felt you could do that, you probably wouldn’t have written in. It sounds like, at least right now, celebrating with Steve’s family really makes you pretty miserable. So you shouldn’t do it. Tell Steve to have a conversation with them about why you won’t be participating—at least for now—and hope for the best!

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Seriously, now is the time to make decisions that ensure you don’t end up in a marriage in which you can’t be yourself because you’ve been putting on an act since you started dating. Same thing for medical cannabis use. Steve—or you and Steve together—should explain it to them, and be prepared to observe their reaction and think about what it means for your relationship. There are possibilities between “totally on board” and “absolutely won’t accept it.” They might be quietly judgy but tolerant. Maybe you can live with that; maybe you can’t. The bottom line is that you have to decide you deserve to be part of a family that accepts you and makes you feel good, and that means being brave enough to leave if this turns out not to be that family. But at least give them a chance to be agreeable before you decide that these two harmless issues are going to destroy your relationship with them.

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Q. Already out and proud: I (he/him/his) have recently been starting to see this guy. He’s very kind, handsome, and humble. I’m attracted to both his personality and looks. He shows a lot of interest in me, and I’m very interested in him. But I’m unsure of how to proceed with this intimate friendship/relationship. He comes from a country and culture that does not accept any form of LGTBTQ+ relations. He said he’s afraid to come out because his family might “kill him,” and I’m afraid he might’ve meant that literally, even though most of his family lives in other countries far away.

I don’t want to get hurt but I like this guy. I’m 100 percent out of the closet and he feels the need to suppress his gay side. He likes spending time with me in public as friends, and we are intimate behind closed doors. What do you think I should do?

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A: It sounds like this guy has a very sad but very legitimate reason not to come out—and there’s nothing that suggests his situation will change anytime soon. On the other hand, you have a very good reason to worry that you’ll eventually be hurt by a relationship that has to remain a secret. I don’t think you need to break up right this minute, but you should be open with him about how challenging this situation might become for you, and then commit to checking in with yourself regularly and being honest about how you’re feeling. When the moment comes, a few months or a year down the line, when getting hurt starts to feel more like something that is happening rather than something that could happen, promise yourself that you’ll take a big step back.

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Classic Prudie

My husband, “Barry,” and I have been married for 23 years. We have four children. I thought we were happy until, about a year ago, Barry began picking fights with me. I finally convinced him to join me in marriage counseling. We saw “Dr. Mary” individually and as a couple. Slowly, Barry admitted that he’d like to open our marriage. Dr. Mary was supportive of this and encouraged me to open my heart to the possibility. As Barry and I began communicating more healthily, I warmed to the idea. Then I discovered evidence that Barry had started cheating on me around the same time he started picking fights. When I confronted him, he told me everything—that he tried to find faults in our marriage to justify cheating and, even more shocking, that Dr. Mary knew about his infidelity. She told him to keep the affairs a secret, explaining that it could destroy our marriage if I found out.

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