Dear Prudence

Don’t Speak

Prudie counsels a woman whose co-worker kept coming over to fool around but never talked about it.

Mallory Ortberg
Mallory Ortberg.

Photo by Sam Breach

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. Confused colleague: I’m a bisexual woman in my early-30s. About a year and a half ago, I met a woman at work and we really hit it off. It never occurred to me she might be attracted to women also. Colleagues told me she’d never dated and was not interested in doing so. As we spent more time together, things took a turn for the physical. It started with snuggling up on the couch for TV marathons, and then she started coming over most days after work to cuddle with me on my bed. We never had sex, but we were very physical with one another. I could tell it turned her on, but tried to be respectful of her boundaries, as I knew she was inexperienced and possibly conflicted, so we never had sex. Then she suddenly withdrew. As soon as I tried talking to her and asking if the sudden distance was the result of our sexually charged interactions, she both vehemently denied it and simultaneously made up excuses to not spend time alone together anymore. She also said that, for her, it was more friendly than physical. She came over one more time (at her insistence), and we fooled around again. Then she withdrew again.

I’m fine with just hanging out in a friendly fashion, as she has become important to me, but want her to acknowledge that she was either into me or led me to believe she was. Surely friends do not spend hours with their hands under each other’s shirts? I just need her to say so for closure, because I really did like her. Am I being selfish? Part of it is that I can’t really talk to anyone about this, as she was adamant our colleagues would not be told of this (which I guess was part of the thrill at first), so no one really understands why things are suddenly so awkward between her and me. I feel like a teenager again, though I’m in my 30s!

A: You are not going to get closure from this woman. She is not even capable of acknowledging that the two of you have been fooling around; she is not suddenly going to go into detail about why she wants to stop hooking up. I don’t know if she’s closeted or sexually conflicted or what, but she’s made it very clear that she’s not interested in continuing to hook up with you or discuss it, and you have to respect that. You don’t have to like it, and you certainly don’t have to put up with that kind of treatment from future sex partners, but you can’t force her to see what happened between the two of you the same way that you saw it. Anyone who invites themselves over to your house to fool around, then wants to pretend it never happened, is not someone you should pursue.

I don’t believe, based on what you’ve said in your letter, that you intentionally ignored any signals or tried to pressure your co-worker into doing anything she didn’t want to do, but I do think this situation exemplifies why asking direct questions is so useful when it comes to navigating sex and relationships. It sounds like she pressed for silence and secrecy, and you went along with it, because you were so enamored with her. Had you said, “I really like what we’re doing, and it turns me on, and I’d like to have sex with you. Is that what you want?” earlier on in your trysts, you might have sorted out the discrepancy in your expectations sooner. (If she’d said “I think of this as a friendly encounter” while she was in bed with you, you could have said, “Ah, well, I think of this as sexual. We must want very different things,” and moved on all the earlier.) As it is, I think you’re going to have to stay strictly professional with this woman at work, and stop asking for an explanation as to why she dumped you.

Q. Rescinding dating endorsements: At my recent wedding, a good friend of mine took home my wife’s ex-girlfriend. Before they left together, my friend asked me discreetly if the ex was all right, and I said sure—my friend is always complaining about how hard it is for her to meet women where she lives, the ex is witty and fun, and I was drunk and figured this had the makings of a great one-night stand. Now my friend is excited about making the cross-country trip to visit her new partner again ASAP, and is sure they’re a perfect match. But I left out one thing—my wife’s ex is a notorious heartbreaker. She rushes headlong into relationships and then dumps people without warning; she’s dated many of our friends with the same result. Should I find a way to mention this to my friend?

A: I don’t think it’s necessary; most adults understand that they run the risk of getting dumped whenever they start seeing someone new. This woman sounds charismatic and a bit reckless (a delightful, if sometimes troublesome, combination). She’s not abusive or a compulsive liar, she doesn’t have a habit of stealing from her girlfriends or cheating on them. She’s just been a serial monogamist thus far. Let the two of them figure things out together. If your friend asks you directly, then by all means mention that she’s broken more than her fair share of hearts, but you’re under no obligation to warn your friend about a fairly common practice in modern dating.

Q. Joke or threat?: My friend “Sophie” is worried about the vibes our other friend “Steve” has been giving her. We’re almost out of high school, and Steve has not been very subtle in his crush on Sophie. He’s not the sharpest knife, but he usually means well. At least, that’s what I used to think. Sophie has gotten rather paranoid about him, to the extent where Steve is no longer invited to her graduation party and he’s blocked on her phone. He’ll make a joke here about her “eating a dick” and a joke there about how she’s “his lady” and he needs to “defend her” (again, they’re not dating—never have). He’s a teenage boy who thinks Family Guy is the height of clever quips, but he wouldn’t hurt a fly. She has asked him to stop making these kinds of comments, and he always either forgets or does it on purpose, because that’s apparently part of the joke too. If he ever thought this was really hurting her, though, I don’t think he’d do it. He’s an idiot, but he’s not a sadist. Is this just teenage boy obnoxiousness, or should I stand by my friend and cut this kid out of my life?

A: I think your friend absolutely would hurt a fly, and you’re not doing anyone any favors by pretending that he doesn’t know exactly what he’s doing, or that what he’s doing isn’t important. If he’s been asked repeatedly to stop making sexual jokes and comments about Sophie, and continues to make them, he is actively and intentionally causing her harm. If she’s had to block him from calling her, you can bet he’s made more than a nuisance of himself on more than one occasion. Sophie isn’t “paranoid,” she’s frightened. Worse yet, Steve’s pretending not to know what he is doing, which is both disingenuous and craven. She’s made a direct request and he’s ignored it; how can you pretend he doesn’t know that he’s hurting her? You should support Sophie and tell Steve to stop making crude jokes at her expense; if he continues after you’ve made yourself clear, it’s time to reinforce your words with actions and tell him to leave you alone, too.

Q. Huge crush on co-worker: I recently started a new position in a new city, with the same company I’ve been with for many years. It’s been fantastic. There’s one problem: I like my co-worker. It was an immediate spark for me—from the moment we started talking, I liked him (which hardly happens for me!). I tend to be bad at reading these things, but I think the feeling is mutual. We sometimes stay an hour after we’ve both finished work just to talk, and we communicate after hours via text. We make each other laugh at work constantly and have opened up to each other about past relationships. Talking to him is as easy as talking to my best friend. We went out for a “quick drink” last week, and it turned into drinks then dinner then chatting in a park, though nothing physical happened or has happened. Assuming I’m not misreading signs of friendship for signs of more (I am hilariously, historically bad at this stuff), this whole thing is a terrible idea, right? A couple of my friends have told me to “go for it” since we are both single, but I think it’s a terrible idea and that I’m flirting with disaster. We work in a relatively small department and frequently work on projects together just the two of us. I also believe dipping your pen in the company ink is just generally a terrible idea. Should I shut this whole thing down now before it gets any more complicated?

A: Let the last co-worker letter serve as a reminder of just how bad office entanglements can get. If you’re historically bad at reading signs of romantic intent, work in close quarters with the colleague in question, and generally believe dating a co-worker is a bad idea, I don’t think you should go for it. There’s no smoking gun in your letter, either—what you describe could be the beginnings of mutual attraction, but it’s just as likely that he only sees you as a good friend. This sounds like the beginning of a fairly bog-standard “office wife” relationship to me. Lots of people develop close friendships at work, and “making each other laugh” and “going out for happy hour after work” don’t necessarily mean he’s interested enough to risk dating. Keep enjoying his company at work, set a reasonable limit on the after-hours texting, and look for dates elsewhere.

Q. Homeless generous mother: I know how much you LOVE “How do I say this nicely?” questions, so here’s one for you. I’m a 26-year-old who grew up with an abusive hoarder father and a co-dependent mother. Because of the hoarding, I don’t keep stuff in my apartment that I don’t need or love. My mother has been homeless and jobless since she and my father divorced, crashing on siblings’ couches and living off of what little divorce money there was.

When a holiday rolls around, she likes to send me a box of dollar-store tchotchkes as a gift. These almost always go right in the trash. If and when she notices they’re gone, she gives me guilt about how she has so little money but she spent it and I wasn’t grateful. I’ve given suggestions like “I miss your baking so much, I’d love if you sent me some cookies” or “How about when you’re in town next we can do something fun together for my birthday,” but I still get the box of crap. Do I save the hurt feelings and continue contributing to a landfill or put my foot down and say, “Please stop sending me things?”

A: Say “Please stop sending me these things. You know I don’t use them, and the money would be better spent elsewhere.” Your mother has already noticed that you don’t keep the boxes of junk she sends you, so you’ve already hurt her feelings; there’s nothing to be lost by being direct now. It’s likely that your request won’t change her policy of mailing you finds from the dollar store, but at least you’ll have made yourself clear, and you can either recycle or donate the unwanted items knowing you’ve done your due diligence.

Q. How do I ask about a present that hasn’t been acknowledged?: Is it rude to ask a friend if they’ve received a present I sent them that they clearly haven’t acknowledged? This has happened three times. It’s not that I want a big “thank you”—I just want to know if the present has been received. (In this last case, I tracked the delivery online and it apparently arrived, but maybe I got the address wrong?) Are my friends just thoughtless? Is there a way to inquire about the gift without seeming demanding?

A: “Hey, did [name of present] ever arrive? I wanted to make sure it wasn’t lost in the mail,” delivered lightly and without subtext. If the answer is “Yes, and I love it—thank you!” your problems are solved. If the answer is “No, what present?” you know you have an issue with your delivery service. (If the answer is “Yeah, it came” and nothing else, you might consider buying them fewer presents.)

Q. Is this feminism or foolishness?: I’ve been living with a man for seven years. We’re both divorced. He has two kids, 26 and 16 years old, and I have none. I have a nice nest egg in the bank. “Tim” was in the process of going bankrupt when I met him, and I figured, I love him; he’s been through a lot; why shouldn’t I help support him and his kids? He works and is well-paid, but things are tight for him owing to child-support payments. Fast-forward to now. I pay the mortgage, I pay the car payment, I pay the condo fee and the homeowner’s and car insurance, and I usually pay when we go out to dinner. I’ve paid thousands in school tuition and dental bills for his older kid. I am paying for a three-week trip to Europe that Tim and his 16-year-old and I will be taking soon. It drives me crazy that he never says, or seems to feel, things like, “Thank you for all you do for me and my family.” His position is that gratitude is poison to a relationship. My feeling is that Tim isn’t doing our relationship any good by seeming to take for granted what I intend as kindness and generosity. Can you bring one or the other of us around so that he doesn’t feel like a toady but I don’t continue to feel taken advantage of?

A: Gratitude isn’t poison to a relationship. What an absurd thing for your boyfriend to say! Gratitude is a gracious and delightful thing that’s necessary for love to flourish. That doesn’t mean Tim should rise every morning and prostrate himself at your feet, although it sounds like he’s implying that is what you want from him. What you’ve described here sounds less like a relationship between partners doing their best to build a life together despite a financial imbalance, and more like passive exploitation.

There’s nothing wrong if one partner makes more money than the other, but it doesn’t sound like the two of you make financial decisions together, or that Tim has ever had a plan for rebuilding his finances after bankruptcy beyond just letting things happen to him while hoping for the best. You two have a long-overdue conversation about what you’re able and willing to pay for in this relationship. His oldest child is an adult and his other child is only a few years away from no longer needing child support—surely it’s time to re-evaluate who pays for what. Because you’ve paid for everything in the past is not a good reason for you to continue to do so indefinitely. Take a look at your finances together, and have an honest conversation about what you both can (and want to) contribute. If you two were equal partners and you felt comfortable paying for your boyfriend’s trip to Europe with his child, I don’t think there would be a thing wrong with it, but if you feel imposed-upon and resentful, and Tim is telling you that by asking him to acknowledge your significant financial contributions you’re “poisoning” your relationship, then something needs to change. It’s telling that you want Tim to thank you for what you do for him and his family; this suggests to me that you’re not quite sure where you fit into it.

Mallory Ortberg: That’s it for this week, everyone! I’m going to go offer up a quiet prayer of thanks that I have never been attracted to a co-worker. Take care of yourselves.

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