Dear Prudence

Help! My Co-Worker Is a 37-Year-Old Virgin. Should I Take Her on a Pity Date?

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

A man in a lab coat eyes a woman in a lab coat.
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Daniel Mallory Ortberg is online weekly to chat live with readers. Here’s an edited transcript of this week’s chat. 

Daniel Mallory Ortberg: Good morning, everyone! Let’s chat.

Q. Not Mr. Darcy: I’m a 45-year-old man who has been divorced for four years. I’ve become close to my co-worker, “Susan,” who is a 37-year-old single woman (I’m not her supervisor). In fact, I’d say she’s my best friend. We work in the science field, and besides being caring, kind, and funny, she’s the smartest person I’ve ever met. We frequently hang out after work and on weekends. I’m a good-looking guy with a professional job, and I’ve never had a hard time getting dates with beautiful, smart women. After a few drinks the other night, Susan confessed to me that she’s a virgin and has never even been on a date or kissed a man. Immediately after telling me this, I could tell she was really embarrassed; she’s very shy, and quite average, physically speaking.

This moment was more awkward for both of us because it is very plain she has feelings for me. I felt heartbroken for her. She’s a good woman and deserves to have some experience of romance. I don’t want to lead her on. But it would cost me nothing to offer her a kiss or give her the experience of a date (she mentioned how she’s always fantasized about holding hands during a movie). Can I offer her these things as part of our friendship, while making it clear we are only friends? I know I should give her a speech about how she’ll find the right guy if only she puts herself out there, but to be honest, she’s incredibly introverted, average-looking, and a virgin—I don’t know a lot of guys looking for that. Please advise.

A: Please do not offer a pity date to a woman—your best friend!—you twice describe in your letter as “average-looking.” Even if she does have feelings for you, it doesn’t necessarily follow that she’s desperate for you to plug your nose, avert your eyes, and eke out a condescending kiss, or to hold her hand during a movie, all the while reminding her that you two are “only friends” and that this is merely a two-hour fantasy you’re willing to let her rent from you. It would be cruel.

Nor should you give her a speech about how she needs to “put herself out there.” She said more than she intended to after a few drinks, and then retreated. I think the best response for you would be to say: “I’m not sure, but I thought you seemed like you wished you hadn’t brought up dating and sex with me the other night. I’m so sorry if you felt vulnerable or uncomfortable. We don’t ever have to talk about it again if you don’t want to, but I honor and value your confidence.”

She hasn’t asked you for advice, or to offer her the Boyfriend Experience, so don’t get ahead of yourself here. This is not a situation she has asked you to solve, and I think particularly because you two are best friends, and you are clearly not attracted to her, you should avoid ever muddying those lines. Just be a friend.

Q. Mary Jane: I work for a large organization, but in a small five-person department focused on teaching youth advocacy and public health programming to high school students. The major objectives have been substance abuse and addiction prevention, as it relates to alcohol, tobacco, and opioids. Recently my team members have begun incorporating anti-marijuana components into the curriculum. To this point, I’ve gone out of my way to keep my opinions to myself around marijuana. Everyone has different views and there is quite a bit of conflicting information about marijuana’s benefits and risks. Generally, though, I feel like the country is shifting to the social acceptance of marijuana use, both for medicinal purposes and for recreation. At the very least, marijuana has fallen greatly on the list of “dangerous substances.” Today my supervisor told me that the funders of the program I teach want to shift gears from the current topic to marijuana prevention. I am against this. I am someone who has a medical marijuana card. I am someone who uses marijuana for a number of mental health issues. I have friends and family who use marijuana medically and recreationally. A number of the young people we work with use marijuana to cope with various traumas, and while I believe the education around brain development needs to happen, I would much rather see a young person use weed to cope and still show up to school than see them addicted to opioids or overdose via alcohol poisoning.

I am not comfortable preaching one thing and living another. How do I go about discussing this with my supervisor? Everyone on the team is staunchly opposed to marijuana usage and has assumed that I am as well. Do I come out and share my personal story in the hopes they are understanding, or do I have to resign? My fear is that if I share this part of myself with my team, they will begin to watch me a little more closely (as they’ve done with some of the youth they’ve accused of “coming to class high”).

A: Definitely do not disclose your own relationship with weed to your co-workers. You absolutely cannot trust them with this information, and you really don’t need to in order to advocate for a different approach. Lots of people are broadly supportive of legalizing and destigmatizing marijuana, releasing and offering reparations to people imprisoned for marijuana-related offenses, advocating for the various medical benefits, etc., without also using it, either recreationally or as part of a medical treatment. You can talk about studies, statistics, and the lack of overdoses, and advocate for, at the very least, putting it way down at the bottom of your collective list of concerns, without either overstating the positive claims about its use or bringing your own personal experiences into it. But I think you’d have cause to worry about losing your job, or at the very least being treated differently at work, if you disclosed your personal experience, and I definitely don’t want that for you. Obviously if it’s only you against one of your primary funders, you’re going to be fighting an uphill battle, but I think it’s a fight worth getting involved in.

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Q. I feel like I’m an accomplice: My best friend “J” was diagnosed with genital herpes over three years ago and has not disclosed it to a single sexual partner since. I’ve tried talking to her about it, but she doesn’t seem to take it seriously. This has bothered me all along, but lately it’s been eating me up. She recently got into a serious relationship (the first since the time before her diagnosis), and he seems like a really good guy. He has even expressed concern to her about getting genital herpes and told her that if she had it and wasn’t telling him, he would dump her as soon as he found out. Yet she is still having sex with him without any form of protection. What is my obligation in this situation? I do not want to lose this friendship, but I feel awful standing by silently. What should I do?

A: That’s such an oddly specific ultimatum (“If you have this one particular STI and you’re not telling me, our relationship is over”) that I have to wonder if this “open secret” is not really a secret at this point. What’s especially odd about that is that it either suggests that: 1. There’s already been a pretty significant breakdown of trust between the two of them, or 2. He forgot that he’s allowed to say, “Hey, let’s go get tested together so we can make informed decisions together about what kind of protection to use during sex.” I realize that sounds like a ’90s-era ad for a free clinic, but if you’re that worried about herpes and you’re not 100 percent on your partner’s willingness to disclose, you do have options!

I don’t know if your friend’s boyfriend has said this in front of you (in which case, theirs is not a relationship I see lasting much longer) or if she’s just continued her habit of oversharing with you, but either way, I think you have a real complaint to make about having confidential information pushed on you that you didn’t invite. I also don’t know whether she’s on anti-viral medication to manage and suppress outbreaks—if she is, you might breathe easier, because it’s fairly effective. But if she isn’t, I think it’s fair to tell her: “Look, I didn’t ask to know any of these things, but I know your boyfriend is particularly anxious about herpes transmission and that you’re not using protection against transmission. What do you think is keeping you from being upfront with him about this? There are a lot of ways to minimize those risks together, and I’m not comfortable keeping this secret from him, knowing how seriously he feels about it.” If you feel like you’re going to tell him unless she does, I think you should be honest with her beforehand so she has at least one chance to do it herself—and I think you should be prepared for the possibility that your friendship may not survive this impasse.

Q. Cleaned out our food: For the past year, we have had a twice-monthly cleaning service that is a gift from grandparents while we raise young children. It’s through a local service in town. There is a language barrier, but the same women usually come. There have been several mishaps, like a broken antique, or a toilet lid destroyed, but nothing we have ever felt the need to “report.” Lately, though, I have been noticing food missing. Nothing significant, more like sandwiches and drinks. The television is also sometimes left on channels we don’t watch, and the women take longer than normal to clean.

We do not stay in the home while they clean so we are out of the way. We don’t have much of value that would be accessible, so I’m not very concerned about theft. We are not wealthy and don’t live in a large home, so I don’t know whether they perhaps feel more comfortable here or think we are less likely to have cameras. My husband and I are in agreement that we would feed them if they asked, so we do not want to say anything that could compromise their employment. We have passed kids’ clothes and toys on to them before and will happily share what we can. However, do you think there is any concern that they think we are idiots and are taking advantage of us? We could always find an excuse to end service without causing any problems for anyone involved.

A: I do not think you are idiots! But neither do I think that the missing sandwiches are a cover for a more complicated, Ocean’s Eleven–style heist these women are planning to stage. Generally I think the simplest explanations are usually the best ones. I think if someone is taking food without asking, it’s because they’re hungry and worried about how hungry they’ll become if the answer is “No.” (Also, many people are not eager to disclose that they are struggling financially, especially to an employer they rarely see.) In that case, the answer is simple: Make sure that they do not have to ask a question they may find embarrassing or difficult.

Leave out a few sandwiches (and/or chips, granola bars, fruit, whatever) and drinks on the counter for the women who clean your house before their next appointment. Leave a note (if you’re at all familiar with their language, try writing it in theirs), but find some way to make it obvious that this is for them. When you return home after they have finished cleaning your house, if the television is on, go ahead and turn it off. That should take about two seconds, possibly less. Be reasonable! There’s no harm done there.

Now, when it comes to something like appointments running overtime or damaged possessions, it’s perfectly fine to speak to them and ask them to be more careful, or tell them that you’ll need to start scheduling on different days if the job now takes three hours instead of two. If you’re not able to speak to them about this because of the language barrier, I don’t think it’s necessarily “reporting” to speak to their coordinator about making a change to the schedule, especially if you frame your request or suggestion in a neutral tone. It’s perfectly reasonable to ask, “Can you make sure your crews don’t use this cleaner on the toilet seat? It stained ours last week,” or “Is it possible to get an estimate for how long the job will take next week? We’d like to be home by 12.” You don’t have to come up with a “plausible excuse” to sneak out of your housecleaning arrangement. Prioritize, figure out what things actually matter and what things really don’t, be generous where you can, don’t make sure someone has to ask you for a sandwich, do feel free to ask people to be careful when they break antiques, and get comfortable turning your television set off once every week or two if they forget.

Q. “Ruining” my brother: I have a difficult relationship with my younger brother. We both grew up in a very religious and conservative household. Ever since I came out as a lesbian, he has refused to stop going to the church he attends (it’s anti-LGBTIQA+), used homophobic language, and supported anti-same-sex-marriage campaigns. I love my brother, but I don’t like him very much. He recently got a big promotion at work. To celebrate he threw a party at a local brewery, paid for a couple hours with an open tab, and invited his co-workers to attend as well as some friends and family, including me. I know a couple of his co-workers through a mutual friend, and they’re gay. I started talking with them, and during the conversation, I tried to apologize for my brother’s homophobia. They thought my apology was a joke and believed my brother to be a great guy to work for. I started hearing about how he’s always supporting them, letting them take time off to deal with their families or kids. They thought he was the best boss they’d ever had. They even love that he pays for Chick-fil-A sandwiches once a month for the office and offers them free “hate chicken.” They know about his religion and his opinions—he told them about it! But they didn’t care because he treated them well despite working to make their love illegal. I got so mad hearing about how they’re willing to not just be polite to but genuinely like someone who hates something so fundamental about them. I was also furious at my brother for thinking he can get away with being a hateful bigot by just buying his co-workers sandwiches and “joking” about his real beliefs. I eventually found one of his bosses at the party and started to challenge them on why they’re promoting someone who is an enemy of the LGBTIQA+ community. They ignored me and soon my mother came and tried to get me to leave; she said I was trying to “ruin” my brother. I got upset at her, demanded to leave, and did. I don’t believe I did anything wrong. I stood up for myself and my community. My parents think I should apologize. My brother acts like he has no idea what happened, but I think he’s lying. He shouldn’t be allowed to get away with this, but it hurts so much to think he will. What should I do?

A: I think it’s time to accept that your relationship with your brother has broken down to a point that, at least at present, is beyond repair. Trying to get his co-workers-turned-employees (the people who may now depend on him for their paychecks and aren’t in a strong position to apply pressure) to challenge his homophobia at work is, I think, a sign that you no longer feel he’ll listen to you. Bringing his boss into it was, at best, a strategy that was unlikely to pay off—it was a desperate and strange Hail Mary.

I’m truly sorry that your brother is homophobic and treats you alternately with bigotry and indifference, throwing homophobic slurs around one minute and then inviting you to a beer bash like nothing’s happened. But I think right now you’re trying to fight a losing battle, trying to insist that your parents or your brother’s friends or colleagues or boss start caring about his homophobia, when they’ve already made it pretty clear they’re perfectly willing to work around it, or pretend it doesn’t exist, or pretend it’s a joke, or find some other form of compromise.

What I want for you is to give yourself the gift of distance from this situation, and not to continue wasting energy trying to convince everyone else to leave him too. What would it look like if you didn’t spend any time or energy tomorrow on your brother’s homophobia or your parents’ accommodation of it? What might you spend your time and energy on instead? I can see it hurts you to think he might “get away with” being homophobic, but right now the person who seems to be suffering the most is you. Whatever he does or doesn’t get away with is less important to me than you getting away from your homophobic family. That doesn’t mean you have to commit right now to never speaking to any of them again. It may be that someday down the road you decide you’re comfortable with some limited surface-level contact, but right now you need to get away from your brother for your own sense of peace and equilibrium.

Q. Am I allowed to identify as bi? I have spent most of my adult life questioning my sexuality after a makeout session at a sleepover at 17 left me wanting more. I am a woman who has only been in relationships with men. During my last year of grad school, I finally added women to my dating profile and had sex with a woman. It was amazing. But it’s only happened one other time since. After that, I excitedly announced to all my friends that I was bi, but now I often get the question of which gender I prefer. At the beginning I said I didn’t know and that it was too early on the journey to tell. This seems to surprise people. I feel like I don’t have enough information yet to make a decision, but I also know that I have never had a crush on another woman. However, I have felt a strong attraction to some women over the years.

Is it wrong to continue calling myself bi when I don’t know if I fall 50-50? Realistically I know that sexuality is a spectrum and you don’t have to be 50-50 to be bi, but I seem to get a lot of pushback from people if I say I am. Such as, “You’ve never dated a woman?” People seem to have this weird obsession with quantifying gayness. Recently I have just explained that “I don’t discriminate when it comes to sex” and have gotten approving nods in agreement. I guess I am just looking for your input? Am I bi? How should I identify? I just don’t know.

A: I don’t think “Am I allowed to come out as X?” is especially useful framing, even though I get a fair number of letters organized along those lines. There is no LGBTQ elder council that can either permit or disbar any individual from coming out as whatever they like, or from using whatever kind of language they deem most appropriate for themselves. You may come out as bisexual and find you experience biphobia, or simply experience some questions you don’t know the answer to (some of those questions may be rude; some of them may be open-ended and well intended; some of them may fall somewhere in between), or don’t immediately find yourself met with a clearly organized community ready to make sure you finally feel at home in your own body and your own life. That doesn’t necessarily mean you aren’t really “allowed” to call yourself bisexual, or even that you’ve made a mistake. It just means that coming out isn’t the end of the process of self-determination or community-building. Nor do I think you should necessarily look to “approving nods” in order to gauge whether you’re coming out properly.

I think the kind of question you should be asking yourself right now isn’t “Am I bi,” or “Should I call myself bi,” but “What am I looking for when it comes to dating, sex, community, and friendship?” Do you want to spend more time with other bisexual people? Do you want to try to date women more actively? Do you want to expand your idea of what a “crush” can possibly look like? You’ve described sex with a woman as “amazing,” wanting “more” after kissing another woman, and feeling a “strong attraction” to various women over the years. I’m not sure why you think none of that qualifies as crushlike. Or, rather, I think I know you’re being unusually hard on the part of yourself that’s interested in women, possibly because you’re hyperanxious about “bothering” other women with the part of your sexuality you don’t consider sufficiently road-tested. You are setting the bar too high here! Based on what you’ve written here, I think it’s pretty clear that you’d like to date, kiss, and have sex with more women, and quite possibly seek out other gay and bi women as friends. I think that’s a great idea and that you should do it. Don’t force yourself to answer a lot of theoretical questions from possibly well-meaning but not especially helpful straight friends about what percentage of your sexuality includes women. That sort of question isn’t especially interesting. I think specific questions, rather than general ones, are more useful in determining what one wants to do next: “Do I like her? Do I want to go to such-and-such gay bar? Do I want to explore this type of persona? Do I want to try this women-only dating app?”

Q. Great guy or secret creep? I work seasonally for a local business owner in my tourist town. I started working there one month out of the year a few years ago to supplement my income, and also because the owner was a great boss and a seemingly great guy! The business has an attraction that requires participants to lie down (nothing inappropriate, just a fun lure to encourage people into the shop). A woman recently lay down on this prop while wearing a skirt and revealed she wasn’t wearing underwear under her fishnet stockings. I quickly looked away, but I noticed my boss taking a picture of her exposed rear end. I want to give him the benefit of the doubt and assume this wasn’t creepy or malicious. I’ve always admired his respect toward women and devotion to his family. But any attempt to justify his action seems impossible. Is there any possibility for an excuse for his behavior? How do I move forward with him as my employer?

A: No, there is not a different explanation for what you saw. No, there’s not a noncreepy explanation for asking a woman to lie down and then secretly taking an upskirt photo. Horrifyingly, this is often legal behavior, even when the victim in question is a minor. But come on: What kind of benefit of the doubt can you offer here? “Oh, I needed a picture of her legs in stockings for medical reasons?” Go ahead; take all the time in the world and put your faculties to full use. Exhaust your imagination. Come up with any and every excuse you can think of, and tell me if any of them sound anything less than ridiculous. His finger slipped, and he took the picture by accident. The camera was haunted. His parents were killed in a terrible fishnet stocking accident years ago, and he needs evidence that this was the same pair of legs responsible for their untimely deaths. I’m sorry to come down so hard on you, but you must know that the simplest explanation is the only possible explanation here. You’re in the lucky position of not needing this job in order to keep a roof over your head, and what you saw directly contradicts your former belief that your boss is a great guy who respects women and that the whole “come in my shop, go ahead and lie down” scheme was and is totally innocent. Tell him what you saw and that he needs to delete the picture and stop doing it. Don’t give him an opportunity to try to claim you hallucinated it, and don’t make “moving forward with him” your goal.

Q. Everyone else has the issue: My wife is a lesbian and I am nonbinary. We’re not in a romantic relationship—we’re best friends who are choosing each other to spend our lives and have a family with. The problem is that most people see me as a woman, and when my wife talks about being a lesbian, even well-meaning family members (particularly her mother, whom we live with) get a little confused. I know I don’t owe anything to anyone and I reckon the constant misgendering is just something I have to deal with as long as I’m perceived as a woman, and one day if I look different, she’ll have to deal with her identity being questioned instead (although I think she cares much less than I do). But it frustrates and weighs on me that I feel like I have to explain our already unconventional relationship to assert my own gender. How can I navigate this? Does it just come with the territory?

A: I think the more relevant issue here is the fact that you two aren’t in a romantic relationship. There’s nothing inherently contradictory about your wife’s lesbianism and the fact that she’s committed to a nonromantic partnership with her best friend. If you would like to correct people when they misgender you, please do; this will not stand in opposition to your wife’s sexual orientation. You say you already have to explain your unconventional relationship, which does sound tiring, but the upside of being out about the nature of your relationship means that you don’t have to uphold a fiction about being romantically involved. Being nonbinary, getting misgendered, and having to explain or communicate something about your identity to people often can all be real challenges, but I think you’d have to deal with that even if you weren’t with your wife. Please give yourself permission to offer whatever clarifications you like.

Q. Re: Mary Jane: These are youths the letter writer is working with. Youths should not be taking mind-altering drugs. Nor should they be self-medicating. They are at an incredibly vulnerable stage of life. If they are suffering from an issue, they need a professional—not self-prescribed weed.

A: I think young people do take mind-altering drugs, whether or not adults would like them to. I think the best way to deal with this (and I don’t think I’m advocating for a full Amy Poehler in Mean Girls “just get drunk and high in the house” position here) is to be realistic, to not lie or overemphasize the negative effect of drugs like marijuana, and to advocate for harm-reduction strategies. Nor do I think the letter writer is suggesting that their organization start encouraging young people to smoke weed! They’re just unconvinced that demonizing weed should be their organization’s highest priority, especially as we move toward greater decriminalization and legalization.

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Classic Prudie

Q. My boyfriend gave me the worst gift of all time for our anniversary: My boyfriend has always been terrible at giving gifts. For our eight-year anniversary I gave him lots of hints that I wanted something special. In all the previous years he gave nothing. This year he said he got me something meaningful and stupidly I got my hopes up. On our anniversary day, he gave me his—wait for it—wisdom tooth. He had to have it extracted a few weeks earlier and kept it so he could give me a “part of himself.” I’m upset beyond words. How do I teach an otherwise wonderful man how to give good gifts, without specifying exactly what I want? Read what Prudie had to say.