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.

Dear Prudence,

I recently found out my boyfriend still keeps nudes from his exes (he’s only admitted to one, but there could be more) and that he masturbates to them from time to time. We live in different states, and I plan to move to his city soon. He is a decent guy, and we love each other. He didn’t see anything wrong with it, but to me it feels closer to cheating than to watching porn, mostly because of the personal romantic history. I was upset when he told me about it, but I also appreciate that he told me himself and wasn’t trying to hide it from me. I want us to understand each other’s perspective. But it felt like a betrayal, especially since I haven’t deprived him of nudes of myself. He told me he is sorry he hurt me and says he will delete them. The problem is that I don’t believe him. From previous experience, I know he hates “erasing history,” as he calls it. For example, he had a hard time deleting my own pictures stored in his hard drive. I had asked him to get rid of them multiple times because I was not comfortable with my nudes being stored anywhere. I’m the type who would prefer them deleted once we’ve finished sexting and to send new ones next time. I understand I may never find out the whole story, but I can’t help but hope that I will be able to tell if he’s telling the truth once I confront him in his face. Should I confront him? Am I wrong to equate keeping those pictures to him not giving my feelings and our relationship the highest regard?

You may have a clearer sense of whether your boyfriend’s lying after you two move in together, but I wonder how at ease you’ll feel if you’re constantly scanning his countenance for “tells” whenever you ask him a direct question. The problem here is not that you’re too far away to verify his answer when he tells you he’s deleted the pictures. It’s that you don’t believe him when he speaks. Whether that’s because he’s made a habit of lying or evasiveness in the past, or because you have trouble dealing with matters of trust and suspicion generally, I don’t know. (It’s not clear if he had a “hard time” deleting your old nudes in the sense that he felt sad at your request or that he didn’t actually do it and you caught him in a lie.) A little soul-searching should help clarify the source.

You need to speak to your boyfriend about the fact that you don’t trust him when he tells you he’s going to do something before you move cities. Ask him about his perspective, since it’s important to you that you both understand each other. What personal rules does he follow about keeping nudes from exes? Under what circumstances would he want to delete them? What does he want his exes to do with nudes he may have sent them? Does he consider occasionally revisiting an old gift to be fun or poignant, or is there something else that appeals? What do you expect from him in order to feel respected and cared for, and does he seem interested and willing in the same?

Also, the fact that your boyfriend occasionally masturbates to pictures of former flings may be a point of disagreement between the two of you, but it’s not the result of insufficient nudity on your part. That’s not really how desire works, but more importantly, you don’t have to offer nudes before you can tell him if he’s hurt your feelings, or what you want from him, or to ask him to have a serious conversation about values, preferences, compromises, and limits together. Start talking it out, and good luck! —Danny M. Lavery

From: “Help! My Boyfriend Masturbates to Nudes of His Exes.” (Sept. 24, 2020)

Dear Prudence,

I went to a fairly cliquey college but developed a friendship with another girl outside of our cliques. We remained friends after college, keeping in touch almost daily via Gmail chat, despite living pretty far away. She was my main confidant leading up to my quickly-planned, very small wedding in 2010. Around that time, she began dating a former classmate/friend of ours. She was invited to my wedding but canceled due to a bout of pneumonia. I never heard from her again. I have spent five years racking my brain as to what I did wrong. I called and emailed her, but never heard anything. I was worried that something had happened to her. Recently there was a blurb in our alumni paper that she and the fellow had married. I was so happy to hear she was doing great! I would love to send her my congratulations, but I worry about intruding. Part of me is also still dying to know what happened. It must have been something I did or said, but I honestly cannot think of anything.

She’s gone, girl. You don’t know what happened, and you likely never will. Maybe her now-husband said something in passing about finding you attractive. Maybe she heard a false rumor that you and he were once involved (Shakespeare is full of such misunderstandings and betrayals). Maybe you said something that bothered her—but five years out, you are never going to find out what it is, and if some harmless remark on your part ended a dear friendship without explanation, then she’s not much of a friend. Sometimes there’s no big reason, but people just decide to move on. So be happy she didn’t die of the pneumonia she probably never had, and conclude this is just one of those inexplicable things. —Emily Yoffe

From: “Help! A Friend Stopped Speaking to Me Years Ago, but I Don’t Know What I Did.” (Nov. 4, 2014)

Dear Prudence,

I play the violin, and my boyfriend plays piano. We were supposed to play at my sister’s wedding, but two weeks before the event, I went running in the park, fell, and fractured my arm. I was near my sister’s house at the time and called to ask her to take me to the ER. She was very upset and concerned about how this would affect the wedding. She scolded me for being so careless. I was in a lot of pain and started crying.

Later, when my boyfriend got home, I told him what happened, and he got really angry with my sister. I begged him to let it go. The next day, my sister texted me that I needed to find and pay for another violinist, since her budget was blown and this was my fault. I cried again. When my boyfriend found out, he swore, called my sister, and quit on the spot. I begged him not to, but he told me he wasn’t going to stand by and let her treat me like trash. My sister blew up. We were disinvited from the wedding, although I ended up going with my parents and sitting in the back. They had to use a phone and speaker for the music. I didn’t stay for the reception. When my sister got back from her honeymoon, she sent me an apology text, but she also wants one from my boyfriend for leaving her “high and dry.” My boyfriend refuses. He tells me he will be polite to her face as long as she doesn’t provoke him. I just want this to be over. I know my sister is in the wrong, but can’t my boyfriend just say he is sorry? I feel so stuck.

I’m so sorry about your arm and the way your sister treated you for having an accident. I can appreciate how additionally painful it must feel to be in the middle of an angry boyfriend and an angry sister when all you want is peace. But just because they’re both angry doesn’t mean they’re both equally culpable or stubborn. Your boyfriend is upset because he loves you and saw you driven to tears more than once by your sister’s cruelty and unreasonable expectations. He saw her blame you for an accident that could have happened to anyone, then ask you for money for fracturing your own arm. Your sister is upset because she had to use an aux cord for her wedding. Your boyfriend’s anger is reasonable, protective, and loving. Your sister’s anger is unreasonable, selfish, and ungenerous. It sounds like your sister has a history of acting this way and that you’ve made your peace with it by giving in to her whenever she digs her heels in, because you don’t believe she’ll ever change. But you shouldn’t ask your boyfriend to apologize for standing up for you just because your sister is habitually unreasonable.

I think you should start by refusing to have any more conversations about this over text. Disinviting your own sister from your wedding because she fractured her arm is a capricious, heartless thing to do, and sending an “I’m sorry” text a few weeks after the fact does little to mend the damage she caused. I don’t think this will be “over” if your boyfriend were to apologize to her. It would likely encourage her worst impulses, and she’d continue to abuse and take advantage of you both as much as possible. I wish I could promise you that if you’re honest and compassionate with your sister—if you explain to your sister in person just how much she hurt you, how hard it was to be in both physical pain from an accident you couldn’t possibly have foreseen and then disinvited from her wedding—she’d apologize on the spot and commit to a new way of living. But if any kind of meaningful change is possible on her part, and meaningful reconciliation achievable for the two of you, she needs to be able to acknowledge that it’s wrong to try to punish people for getting hurt in accidents and commit to treating you with basic kindness and respect. —D.L.

From: “Help! My Sister Disinvited Me From Her Wedding After I Broke My Arm.” (Nov. 2, 2019)

Dear Prudence,

My boyfriend and I have been together for almost a year now, and I thought it was going well. I thought we were utterly trusting of each other. A few days ago, he sat me down and began to apologize profusely, and informed me that he had been suspecting me of stealing money from him. He explained that for some months he had been noticing increments of his cash was missing, and that his best friend Corey had told him the culprit was probably me. I was floored! Then he caught Corey in the act of sliding a wad of bills from my boyfriend’s emergency stash, and the truth was out. My boyfriend said he wasn’t sure about what Corey had been saying, but that he’d been subtly steering me away from situations where I’d have access to his cash, and that he’d mentioned several times that he thought he’d had more money in his wallet just to gauge my reaction. I didn’t notice at all! He apologized his heart out for not trusting me. I’m really hurt and now I’m wondering how I can trust him, knowing that he didn’t trust me?

I have a Valentine’s Day gift suggestion for you! Wrap up a copy of Othello, and then you and your beloved together watch this tale of murderous manipulation and betrayal. It’s a recurring theme in Shakespeare for an evildoer to whisper lies to one character about someone that character loves and trusts. The person hearing the lies then believes the manipulator, and tragedy is soon to follow. I know it would make the plays shorter and not necessarily better, but I find myself wanting to call out something like, “Othello, just say to Desdemona, ‘Des, honey, Iago told me thou art having an affair. What’s up with that?’ ” It is indeed too bad that upon hearing these vile lies from your boyfriend’s own Iago, he didn’t come to you immediately. He could have explained that Corey had told him something awful he found impossible to believe, and he had to let you know. Together you might have easily figured out what was really going on. Yes, it’s bad that he was so willing to doubt you. But give him some credit for baring his easily-deceived soul—even if an arguably wiser course would have been to keep silent about what a sap he’d been. His apology is abject and sincere. Of course you are hurt and shaken, and getting over this is going to take time. You two need to talk about this, but not dwell on it. If you want this relationship to go on, all he can do is slowly regain your trust. —E.Y.

From: “Help! Someone Told My Boyfriend I Was Stealing From Him, and He Believed It.” (Feb. 12, 2015)

More Advice From Dear Prudence

When I first met my husband, I was really excited to find someone else who liked to have sex at least 10 times a week.