Dear Prudence

Love Hurts

Prudie counsels a letter writer who thinks a tumultuous relationship may be worth the pain.

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. Addicted to heartbreak: I recently broke up with someone who I thought was my soul mate. I’ve always disliked the word, but when I met him there was an immediate connection that I had never felt. It was like you had known this person for years and found them sexier than anyone you had ever met, while being completely intrigued. In the course of a couple of years we had some amazing memories together, but we also fought constantly, and there were countless small and big lies on his part, including nights spent with his ex. The thing is I still love him so much and feel like I am never going to feel that connection again. That feeling is pretty rare, I think. I’m not new to breaking up with people or people breaking up with me—this one just feels … not right. I can’t shake the feeling that I’m making a mistake (my mind says I gave up too easily), but during our relationship I cried at least a few times a week due to our fighting. That’s a shit way to live. How do I move on from this? Why is it that the strongest connection I’ve found (nothing even comes close) has hurt me to my core? Am I only satisfied by emotional pain?

A: I very much doubt that you are only satisfied by emotional pain, especially considering that the constant ups and downs of this relationship were for you the exception rather than the rule. You probably will feel connections again with other people, even significant and profound connections; I can assure you that intrigue and sexual charisma are not the exclusive province of compulsive liars and habitual cheaters. You got burned in this particular instance but managed to extricate yourself, and now you’re dealing with the aftermath of losing access to a lot of excitement, sudden emotional highs and lows, and intense feelings. You’re not going to feel immediately centered and ready to connect deeply with someone else in the first few weeks or months post-breakup. The strongest connection you’ve ever found has hurt you to your core because it was the strongest connection you’d ever felt. That doesn’t make the connection itself somehow fraudulent or mean that you’re only capable of connecting to people who treat you badly, merely that this person had the power to hurt you precisely because you cared for him so deeply. You have it backward if you think you only cared for him because he hurt you.

Q. He’s never cheated, but I still don’t trust him: I have been married to my spouse for more than 20 years. Throughout our marriage, his ex has always been in the picture. She was his first love, but things didn’t work out. She got married before my spouse and I met but has never stopped blatantly pining for my spouse. Honestly, they have a strange relationship (in my opinion). Recently she asked him to go to NYC with her for the weekend. She stated her spouse hates New York and felt that my spouse would be the perfect companion since he loves it. I am not invited. They would be gone for the weekend, sharing a hotel room. He told me I have nothing to worry about. I said not without me. They both told me I am being petty. Am I? It all seems fishy to me.

A: WHAT. No. No, you are not being petty by objecting to a weekend getaway for your spouse and his ex-girlfriend in a single hotel room, and if they’re trying to make you feel as if you’re being unreasonable, that suggests to me that they’re trying to get away with something. What you call “a strange relationship” I’m inclined to call an affair; you say your husband’s never cheated on you, but I think he’s coming awfully close, if he hasn’t already. There are a lot of people who love New York City; she can take someone you’re not married to. I’m not against spouses taking separate vacations, but this is ridiculous—they used to date, she’s still actively pining for him, and they plan on sharing a room. Something fishy is going on, and don’t let your husband and his (ex?) girlfriend convince you that you’re being paranoid.

Q. How much “I” is TMI?: I have a good friend who recently revealed that many years ago a mutual acquaintance had been sexually assaulted and was injured trying to escape her attacker and in the awful aftermath dropped out of school. I was shocked—not only because my heart went out to her but also because I had heard a very different version of the same story from my boyfriend, who was there that night. In his version of events, this acquaintance (also my boyfriend’s ex) was so drunk that she fell down and injured herself. He took care of her all night, but after she recovered they never spoke again. (Although he clearly had feelings for her at the time, they had a bad history.) I don’t want to believe that this acquaintance would lie about being assaulted to get attention, especially because it doesn’t seem like she has told this story to many people, and I hate to think that there is a girl out there who really believes she was sexually assaulted when she hadn’t been. I don’t know this girl well, and my boyfriend refuses to talk to her (like I said, bad history). If you believed you had been victimized, but other people had a clearer recollection of events, would you want to know the truth?

A: I don’t think you have enough information to proceed. All you know is that your boyfriend dislikes this woman and was not a witness to a sexual assault that still may very well have occurred. You weren’t there, and you don’t know the woman in question very well. She’s never even told you herself; you’ve heard from another friend that she believes she was assaulted and from your boyfriend that he believes she wasn’t. At no point has the woman in question confided in you or sought your opinion in any way. She has not publicly accused or pressed charges against any person you believe to be innocent, so there is no third party for you to seek to protect. You have no way of knowing whether your boyfriend actually has a clearer recollection of events, since you were not there yourself, and if he doesn’t wish to speak to her about it, I don’t think you should take it upon yourself to do so for him. Stay out of it.

Q. Re: How much “I” is TMI?: Are you sure your boyfriend isn’t the one who assaulted her? His saying “she fell” and her never speaking to him again after that night certainly could point to a very different conclusion than the one you’ve reached.

A: Oof, that’s a particularly dark possibility I had completely missed on my first reading. It’s certainly possible, and re-reading the letter with that possibility in mind makes the situation particularly sinister.

Q. Want to make up to sister: My sister and I have five years between us. I’m the oldest, and before she was born there were two other boys, one who died at home. My baby brother and I were sent to live with our grandparents, and no explanation was given about the death of my closest sibling. My parents, understandably, struggled, and when our family was reunited, we had moved and my mother was newly pregnant and excited about this new life. My sister couldn’t know what a broken family she was born into, and I was not at all welcoming and still trying to figure it all out. I never did warm to her, and while we shared a room, it was a chilly place for such a young child. I am ashamed today and would like to make it up to her, but she has long ago written me off. I can only speak to my part in it but will say that her side of the street is not spotless. She has blocked me on social media, changed her phone number, refused to see me, and not responded to mail. I’m 72 and not in good health; I’ve given her space for the past 25 years not wanting to antagonize her, but I’d like to try again. Any ideas?

A: I understand your desire to try again to make amends to your sister, particularly as you get older, but the problem with giving someone space is that she gets to have as much space as she wants, as long as she wants. If your sister never wants to speak to you again, even in your final years, she has that right, and you cannot force her to listen to your apology, no matter how much you might like to unburden yourself. There are two requirements for reconciliation, and you only have one of them: You’d like to try again, but she doesn’t, and no matter how strong your desire to reconnect, it can never override hers. Since she’s already refused to answer your letters, I don’t think you should try to send another. If you continue to be troubled by memories of how you treated your little sister (as, I hope you can remember, a child yourself who was also suffering), consider unburdening yourself to a therapist or a spiritual counselor, if you happen to be religious. But don’t pressure her with your own mortality into forcing a conversation she’s decided she doesn’t want to have.

Q. Co-worker with different priorities: I work in a fairly small company with just me and “Helen” in my department. Most of the time, Helen is attentive and effective at her job. But in the past few weeks, she’s decided she wants to start a nonprofit with her husband. I totally support this, and management does too. But it’s getting to the point where she’s prioritizing the tasks for her nonprofit while she’s at work, and I’m left to do our shared tasks by myself. This isn’t every day, but it’s often enough that it’s beginning to annoy me. Our bosses love her and are thrilled she’s doing nonprofit work, so I’m afraid if I bring it up to them I’ll seem like a childish tattletale. But I’m getting a little tired of doing the work of two people. How do I go about asking her to only do her nonprofit work at home?

A: It’s not exactly telling tales if you ask Helen to do her job while she’s at her job. If you two have a good relationship, consider bringing it to her first: “Helen, while I’m really excited for your new nonprofit, I’ve noticed it’s taking priority over your tasks at work, and I’m having to do more than usual to pick up the slack; can we talk about this?” If that still doesn’t work, you can escalate it to your bosses. If you’re still concerned about seeming like a snitch, you can frame it as a desire for clarity and assistance in making sure everything gets done on time, rather than an accounting of Helen’s every minute in the office. But what you’re asking for is eminently reasonable, and there’s nothing childish about wanting to do one job instead of two.

Q. Going to the chapel: My boyfriend and I recently got engaged, and we are both incredibly happy. One thing I’m not happy about: His parents insist we get married in the Catholic Church. I was raised Catholic and have hated the religion ever since. I’m loath to give money to an institution I disagree with so vehemently, and I’m not looking forward to starting my marriage off in the Catholic Church. I was never the type to plan my wedding when I was younger, but now that I’m looking at it, I know I don’t want to get married in the church. I’m not looking for a way out because there isn’t one. I’m just hoping you can give me some perspective. How do I get over it and get happy about being married in the Catholic Church?

A: I don’t think you should get over this. You’re not merely indifferent to the idea of getting married in a Catholic Church—it violates your deeply held principles. You’re the one getting married, and I think you should stand your ground if you truly object to getting married in a church that belongs to an institution you despise. If your fiancé’s parents are using money to try to force your hand, consider getting married at the courthouse and having a party for friends and family afterward. It doesn’t sound like your fiancé is particularly interested in getting married in the Catholic Church, which would be a different story, so I’m not sure why you’ve already resigned yourself to not only losing this fight but forfeiting entirely. At the absolute bare minimum, I don’t think you should force yourself to be happy about getting married in the Catholic Church at someone else’s behest. If you feel your future in-laws are people you are not allowed to disagree with, I would encourage you to reconsider the wedding entirely, before binding yourself to this family for life.

Mallory Ortberg: Thanks, everyone! I especially appreciate the closer reading on the TMI letter—many people seemed to catch a possible second meaning that I managed to miss entirely. See you next week.

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If you missed Part 1 of this week’s chat, click here to read it.