Dear Prudence

Help! I’m a Straight Guy Who Just Slept With My Gay Best Friend. Now What?

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

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Photo illustration by Slate. Photo by GaudiLab/iStock/Getty Images Plus.

Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat.

Daniel Mallory Ortberg: Hi, everyone! Hope you all enjoyed the break—now it’s back to your regularly scheduled Dear Prudence. Let’s chat!

Q. Possibly bisexual: I have always identified as a straight guy, but I am recently panicked and confused by feelings for my best friend (a gay man), “Greg.” We’ve known each other since college and have always been close. I was at his place recently, comforting him over a breakup; we got drunk and slept together. He didn’t take advantage of me. I remember everything. I initiated it, and he asked several times if I was OK with what we were doing. I had to leave early the next morning for a work emergency, so I left him a note (along with a glass of water and some aspirin) explaining why I had to leave. I also texted him the same information, just in case. But he concluded I was angry with him, texted me an upset-sounding apology. He worried that it was his “fault” and that I wouldn’t want to be friends anymore. I tried to reassure him. His response was conciliatory but brief.

I decided to talk to a friend about what had happened. She was excited to hear we had “finally” slept together and started talking about how long Greg had been “in love” with me. She asked if I’d told him I felt the same way. I was stunned. It turns out that she and another mutual friend have known that Greg has had serious feelings for me for years, and that our whole friend group has been waiting for me to “figure out” I’m bisexual because I’m “obviously into Greg.” This is all news to me! I can’t stop thinking about it, and I am putting off replying to a message from Greg asking to meet up because I don’t know what to say.

I barely even know what I’m asking here. Can you come out as bisexual when you’re only really into one guy, and in your late 20s? Have I destroyed my most important friendship by unknowingly messing with Greg’s feelings? Is it worth risking hurting him more by asking if he wants to try a relationship with someone so confused about his sexuality? I am definitely attracted to him, and I honestly don’t think I’ve ever cared about someone as much as I do him. I literally received another message from him asking if we’re OK while writing this question, so please advise in any way you can!

A: I have so much good news for you (You’re doing fine! You do not need to keep apologizing for having sex it sounds like you enjoyed, with a friend you trust and find attractive; your hookup sounded complicated and flustered on a number of fronts but nothing that can’t be ironed out by an in-person conversation), but only one piece of advice: Talk to Greg! Talk to Greg, and only Greg, about this. Not the rest of your friends, not to me, not to trustworthy-looking strangers on the bus who look like they have a lot of wisdom to share. Just Greg.

You are allowed to come out as bisexual in your late 20s. You are allowed to come out as bisexual if you’re only attracted to one of your friends named Greg and haven’t first run a hypothetical attraction test on all the other men in the world. Asking a friend to go out with you is not hurtful. It’s a risk, I suppose, in the sense that asking out anyone is a risk, but it’s not such an inherently risky proposition that you shouldn’t do it. Talk to Greg in person, make it clear that the morning-after work emergency was real and terribly timed and not just an excuse to avoid having a post-sex conversation with him. Tell him that you’re attracted to him, that you care about him, and that you would be interested in going on a date or having sex again or whatever else you’re interested in exploring with him, then ask him how he feels. You don’t need to preface your feelings with speculation about his, like, “I know you probably don’t want to date anyone so soon after your breakup” or “Sarah thinks you’ve been in love with me for years.” He knows that you haven’t dated guys before, so you can let him decide whether that’s a “risk” he cares to run. You don’t have to take yourself out of romantic contention just because he’s the first man you’ve slept with. Good luck having the talk. I hope it goes well, and keep us updated!

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Q. Realistic presents: My brother is dating a woman with three kids. He has never had much luck with women. He tells us that he loves her and she is the “one.” There are plans for all of them to join our family for Christmas. They are flying. My mom texted the girlfriend and asked her for a wish list for her kids. The girlfriend texted back: iPads, Xboxes, designer clothing, nothing under $100. My parents aren’t wealthy people, and I am not buying iPads for kids I have never met! My mother was upset, so I called the girlfriend and told her we needed a more realistic gift list. She got snippy and asked if I got my kids expensive gifts. I told her that was none of her business and she needed to deal with her own kids before worrying about mine.

The girlfriend has twisted the situation, accusing my family of looking down on her for being poor. My brother yelled at me for “sticking my nose in”, and I yelled back that our parents survive on Social Security. Why the hell was his girlfriend hitting them up for expensive gifts? He couldn’t answer that. My brother is paying for this trip. I know he doesn’t make that much. My husband and I planned on keeping our more extravagant presents at our home and letting Santa bring the smaller ones to Grandma’s. I don’t know what to do now. The situation is simmering and I don’t want this to turn out to be a horrible holiday.

A: While I agree it’s rude and presumptuous to send over a wildly expensive wish list, I think the problem really started here: “My mother was upset so I called the girlfriend.” Your mother is an adult who can handle her own problems; she should have given herself a little time to get over her initial irritation and said something like: “I’m afraid all of that’s out of our budget. If you know of anything the kids might want that’s less pricey, let us know.” There was no reason for you to get involved, no matter how angry you got on your mother’s behalf.

One of the unpleasant side effects of sticking your oar in unsolicited is that it sometimes means you have to apologize to people you really don’t want to apologize to. But you do have to apologize to your brother’s girlfriend. Tell her you’re sorry for getting in the middle of her conversation with your mother, that you won’t offer unsolicited advice again, and that you’re looking forward to seeing her at Christmas. Give the same apology to your brother, keep it brief, and don’t attempt to relitigate the issue. Bring whatever presents you feel comfortable bringing to your family Christmas gathering and leave the rest at home.

Q. Homeless kittens: This summer, a stray cat had kittens under our deck. We’ve been feeding them but can’t take them in because I have a 16-year-old diabetic cat who requires special (expensive!) food and insulin. At his age, he just wouldn’t be able to handle the energy of these two kittens. We tried adding a second cat a few years ago and it did not work out. I don’t want to take these kittens in and then have to put them back outside again. (One of them already tries to run inside our house whenever he gets a chance.) Should we take them to our local shelter (it isn’t no-kill) and hope for the best, or set up an outside shelter for them when it gets colder? I just don’t know what is best for them.

A: I think the best thing to do right now is to make sure the kittens have been spayed/neutered. If they’re already comfortable being fed and try to run inside your house, I don’t think it will be too difficult to lure them into a carrier and take them to your vet. And if they were born this summer, they’re definitely old enough to be fixed. You can also check to see if there’s an organization like the Feral Cat Spay/Neuter Project anywhere near you that may be able to offer support/resources like Trap, Neuter, Return:

Trap, Neuter, Return (TNR) is a program that allows free roaming cats to live out their lives without adding to the homeless cat population. Cats are humanely trapped, often evaluated to ensure they are healthy enough to live a free-roaming lifestyle, vaccinated, spayed/neutered, ear tipped to identify them as being altered and released back to their familiar environment. Often kittens and tame cats are placed with rescue organizations for adoption into homes.

You might also ask family and friends if any of them are interested in adopting a kitten. Sometimes people are more interested in young kittens than they would be in fully grown feral cats. If there are no leads there, and no other local organizations are willing to help, then it’s time to contact the shelter. Just because it doesn’t have a no-kill policy doesn’t mean it’s an automatic death sentence; it’s fair to assume that unless you have evidence to the contrary, everyone working there is attempting to do as much good as they possibly can for the maximum number of animals.

Q. Idealistic yet unorganized: I signed up in early November with a local nonprofit to be a secret Santa for children in my area. The due date to have presents wrapped and shipped to their school is in a few days, and the nonprofit still hasn’t mailed the students’ letters! A friend who signed up with me hasn’t received her letters either. The good news is we both ended up bypassing the organization and calling the schools directly to ask what age the children are and which presents they are most looking forward to. We wrapped everything and got it all shipped out in time.

Now quite a few of my other friends are asking which organization I went through because they would like to participate next year. This organization was so unorganized that I honestly couldn’t recommend using it, but I think not recommending this organization would only hurt the children. What should I tell my friends?

A: There are so many Christmas-themed charities that I don’t think you need to make it your responsibility to prop up the reputation of a disorganized one. Find one that’s well-organized and encourage your friends to seek out a charity that can live up to its promise. Plus, there are a lot of ways to help children year-round, like paying off school lunch debts, donating money to your local food pantry, or volunteering at an after-school program. Don’t waste your time trying to fix a flailing organization when there are so many other viable opportunities.

Q. Husband wants books for Christmas. He never reads them: Year after year, my husband asks for books for Christmas. I believe he asks with the sincere intention to start reading more. But in all our years together, he has not once cracked open a book I’ve gifted to him. It shouldn’t bother me—he seems genuinely happy when he unwraps the book. But then the book is quickly forgotten. Our shelves are crowded with titles that are never read, gathering dust. We live in a small apartment, and at this rate, we’ll have to donate them for the sake of space. The idea of boxing up years of gifts to him for Goodwill is depressing. It’d be one thing if they were enjoyed, but again, he never reads them! He wants books again this year.
Should I go rogue and get something he might actually use?

A: I’m tempted to instruct you to wrap up a book you bought him four or five years ago and present it to him as if it’s brand-new. I suppose you could also go the e-reader route and start getting him books he’ll never read to store on a tablet—at least that way you won’t be sacrificing shelf space in your apartment. Or you could donate to your local library in his name. Lots of libraries (the San Francisco Public Library, for example) accept cash donations, and it’d likely still make him feel like a good literary citizen, in the same way promising himself that he’s actually going to read his new books this year does.

Q. Should we break up? I’ve been dating “Sam” for about 10 months. It’s my longest relationship and his longest relationship even though I’m 27 and he’s 33. When we first started dating, we used to see each other about twice a week. We both have busy jobs but made time for each other. He’s never been a very good texter, but in the past few months now I see him about once or twice a month. His job got crazy busy after he got promoted. Seven people have quit his company in the past couple months because it made them work late and on weekends. On the one hand, I understand that Sam is overworked, and he’s also introverted, so he likes to have time alone on weekends. But going from seeing him frequently to hardly ever, compounded by our lack of text communication, is making me consider ending the relationship. Last Friday I asked if he wanted to go out with me and my friends and he said he just wanted to stay in. Then I asked what his plans for the weekend were and he just didn’t respond. Last month I asked him if he just isn’t interested anymore, if our relationship has fizzled for him, and he said that’s not it at all—it’s just how overworked he is. I really like him and we are great when we’re together. Should I just enjoy the time we’re together?

A: I hesitate to sound glib here, but … how can you enjoy the time you’re together if you two don’t actually spend time together? You’ve seen him roughly once a month for the past three months, he’s stopped responding to your texts, and he’s demonstrated no interest in talking to you about when his schedule might potentially open up or how the two of you can stay in touch in the meantime. He has effectively broken up with you already. You can either acknowledge this openly so you can mourn your breakup, move on, and look for someone else, or wait for him to finally get around to saying the words, “I want to break up.” At the risk of making a sweeping generalization—and acknowledging that there’s probably at least one reader of this column who thinks this setup sounds ideal—anyone who is so overworked and introverted that they only want to see their partner once a month or less often probably doesn’t want or need a partner. You deserve a boyfriend who enjoys seeing you and can consistently balance his work responsibilities against his desire for solitude and a social life. That’s not an unreasonable request to make of a boyfriend. Sam may be great in a number of respects but he’s really not your boyfriend at all anymore.

Q. When to disclose that you’re nonmonogamous: I’m nonmonogamous and have been for a pretty long time. One tricky aspect about it is when to disclose this when it comes to dating. I have a dating profile that states I’m nonmonogamous and only looking for same. Recently I had a couple of dates, and really great flirtation, with a guy who described himself as monogamous but indicated in his compatibility answers that he was open to the idea of nonmonogamy. However, I soon intuited that he hadn’t read the fine print on my profile. Usually guys bring that up when they read it, and he hadn’t mentioned it once.

So, I figured I really needed to let him know about this, especially because he seemed way into me and was talking about future dates together. I brought it up during our second date, when we were having post-dinner drinks at a bar. (For scheduling reasons our two dates were a month apart, but a lot of texting went on in between.) In retrospect, I should have set up a time to seriously discuss this, not spring it on him while we were drinking, but I felt like the longer it went unsaid, the more “betrayed” he might feel about it. And boy, he had a reaction. It went from “this is not a deal-breaker” to “Oh my god, I can’t do this, I don’t understand the rules, I should just go” in what felt like 20 minutes tops, and then he rushed out of the bar.

We cleared the air the next day. He apologized profusely for being a jerk and bailing, but clearly, we’re not going to be dating. Maybe this was always how a guy like him was going to react, but when is the right time to bring it up if you meet someone in real life first? Or if it’s clear someone didn’t read the fine print before he jumped straight to heavy infatuation? He claimed his meltdown was an emotional response to the conflict he was feeling between 1) the expectation that serious relationships need to lead to monogamy and 2) the great time he was having with someone who turned out to be (gasp) nonmonogamous. Was there a better way to have shared this information? A time sooner or later? We were really clicking, so his freakout was a huge surprise.

A: I think you’ve done all that you reasonably can to make sure that you’re upfront about being nonmonogamous, and going into detail about your dating style on a second date because you’ve developed a strong feeling that your date didn’t actually read your profile hardly seems like putting off an important disclosure. Nor do I think you “sprung it on him” at an inappropriate time—it was your second date! You don’t say you two were wasted or anything, so it doesn’t sound like his ability to process new information was impaired. You were just getting a drink or two, a perfectly reasonable second-date activity. It’s unfortunate that he freaked out, especially after you’d really gotten your hopes up, but there’s no amount of planning or preparation that can completely eliminate jarring moments or sudden realizations of incompatibility while dating. Certainly you can take something away from this, and you might decide to start explicitly confirming with future dates that they’re aware of your nonmonogamy before you meet up. But even then there’s always the possibility that some of them will say, “Yeah, I’m totally cool with it” when they are not, in fact, totally cool with it.

Q. My father’s memories: My mom died a year ago. Naturally, my dad talks about her a lot. Some of this is sweet, like memories from vacations. Some of it is just inappropriate: I 100 percent did not want to hear about my father’s first seduction of my mother. And some of it is bitter as hell. Over four decades of marriage, there are ups and downs, and my mom got much-needed therapy that started when I was a teenager and should have started when she was that age, so there were frankly plenty of bad times she caused with my generally good-natured, sweet father.

But I need a script to get him to stop. I don’t mind the sweet memories. Hell, I’ll even let go of the less-appropriate memories since at least they’re positive ones. But I need the bitter ones to stop. For all the problems I had with my mom before the therapy made progress, we had a happy, healthy relationship as adults and I loved her and miss her like crazy. He doesn’t have anyone else to talk to, but I’m still not the one who should be hearing this.

A: “Dad, I know that you need to be able to talk about Mom. I also know that your relationship was really difficult sometimes. But I’m your kid, and I cannot be the person you come to about your sex life or marital problems with Mom before she died. I hope you can find a friend or a therapist, or both, to talk to about this, but it can’t be me anymore.”

Then if he does it again, all you have to say is, “Dad, we’ve talked about this, and I can’t have this conversation with you.” Then leave the room/hang up the phone/etc. This is a totally reasonable request to make of him, even while he’s grieving, so please don’t feel like you’re being unduly harsh on a widower or anything along those lines. There’s a whole world of people who are not his kids to whom he can talk about this!

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Classic Prudie

Q. My cousin is a sociopath who dated my friend and stole her identity: My cousin is a sociopath. He recently dated a friend of mine, stole her identity, and then dumped her. Now all our friends are angry with me, because I should cut him off after what he did. Should I? It won’t teach him anything; he can’t learn that sort of lesson, and it might make him worse (it has in the past). Plus, it will upset my aunt, who already has enough to deal with regarding him. Not to mention the rest of the family who see his friendship (such as it is) with me and my brother as a way my cousin can be controlled—and therefore pressure us to stay in contact with him. (He is, or was at one point, diagnosed. My aunt has grown more deceptive over his psych history as time went on.) Read what Prudie had to say.