Dear Prudence

Which Team’s Player?

Prudie counsels a woman who wants to date a possibly straight female co-worker.

Daniel 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. Into my (maybe straight) friend and co-worker: This year, I met a new co-worker (I’ll call her Sara), whom I immediately had a crush on. We quickly became really good friends, and I didn’t want to mess up our friendship, so I crushed my crush. Skip to a few months later and I find out the feelings are reciprocated, but Sara has not been attracted to women before and is confused and cautious. At this point, we work together (not in the same division, fortunately), she’s one of my closest friends, and we hang out almost every day, but our friendship is filled with sexual tension and flirtation. She doesn’t know that I know how she feels, but I’m scared to act. I fear that our friendship will be hurt or that I’ll get hurt because she doesn’t want to act on these feelings. I know at this point I need to do something—what should I do?

A: I’d like to separate two issues here. One is that Sara hasn’t been attracted to a woman before, as far as you know, and is feeling circumspect as a result. The other is that you two are co-workers. If it were just the first, I would say, “Proceed with caution but also joy! Lots of people aren’t attracted to women until they meet a woman they’re attracted to, and it doesn’t make her feelings for you any less real.” Everyone who’s ever dated women has had to, at one point, date a first woman.

But you work together, and you’ve somehow managed to learn of her feelings for you without ever talking to her about them. (How did you do it? A gossipy co-worker? Accidentally read her diary? I’m dying to know!) There’s a very real chance that any attempt at a romantic relationship would end badly for you both personally and professionally. When given the chance to date a co-worker, I think it’s almost always best not to. There are so many other people in the world to date, none of whom you’d have to see at work every day if you broke up!

If you do decide that you absolutely have to have a conversation with her about your romantic tension, I don’t think you should let on that you’ve discovered her feelings. There may be an excellent reason she’s decided not to share them with you. Speak only about your own. If she turns you down, don’t tell her, “But I found out you feel the same way! Are you’re just scared because I’m a woman?!” Take whatever answer she gives you and accept a no as gracefully as you would a yes. Then familiarize yourself with your company’s HR policy on dating a co-worker, follow the rules, and get a dog and a country house together.

Q. Expectations as an aunt: My sister has a toddler, and I am the only family she has in the city to help her out and spend time together. Her expectations of me are high, and she recently called me out for not being a good aunt. I explained to her my health conditions (chronic migraines and depression, especially in the winter), and she brushed off my reasons and excuses and left in tears. She later told me she was here for me when I am ready to deal with the situation and that she loves me no matter what. I took a look at the calendar and in one month alone I saw her five times, including babysitting twice! Before she had a kid, she was fine to keep our relationship more casual. I understand motherhood is difficult, and I felt I was helping her out a lot, only to be called out for not doing enough. What are reasonable expectations of an aunt living in the same city? Should I not be expected to help out less given my own health conditions and the fact that I have my own life? I don’t really enjoy children and am quite introverted, so I am not inclined to want to spend a lot of time with a screaming toddler. Am I the worst? When I asked her what she expected of me, she refused to answer.

A: What a horrible situation your sister has created. She won’t be clear with you about what she wants from you, but she is happy to let you know when you’ve failed to live up to her secret standards. “Helping her out” and “spending time together” are two separate things. She wants to conflate them and to suggest that when you’re unable to babysit her child, you’re also failing to be a good sister and aunt. That’s simply untrue.

It sounds less like your sister wants to spend quality time together and more like she considers you as a source of free child care. That wouldn’t necessarily be a bad thing if your relationship were otherwise healthy, but the fact that she’s making demands of you and suggesting that experiencing chronic illness and depression make you a bad aunt is deeply upsetting. You should decide how often you want to see your sister and her child and make it clear to her what you’re capable of. If it’s once or twice a month, tell her so. If you’re willing to babysit occasionally with plenty of advance notice, make that clear, but tell her not to consider you her first line of child care defense, because that’s simply not something you’re capable of doing. Make no apologies to her for having limitations. There’s not a right or a wrong number of times an aunt “should” see her sister; it depends entirely on the people in that relationship. If her response is to continue to guilt you for not doing enough, back off with a clear conscience.

Q. To clothe or not to clothe: We’re a blended family with three teenage boys who are super close in age. My biological boys are super comfy with their bodies, to the point that we had to institute a “you gotta at least wear pants downstairs” rule to avoid any discomfort to guests. My stepson doesn’t fall into this category, which is also perfectly fine—we’re very much a “you do you—we love you anyway” family. He’s a great kid—he rarely causes me any stress or anxiety (unlike his brothers, bless all our hearts) and recently told me that he’s gay. He told me he’d already confided this to both of his brothers months ago and that it’s just really not a big deal around here.

We also have two daughters who are both in college. I know that if my daughter was walking around the house in her bra and panties in front of her brothers, I’d have told her to go put clothes on, so is this now a double standard?

Am I a prude for thinking that my stepson might be uncomfortable with his stepbrothers walking around in their skivvies upstairs (and occasionally downstairs until they get “the look” from me)? He’s not one to say something if he is, and I fear that he’d be super embarrassed if I asked him about it. But what if it is something he’d like help with? And what if asking him how he feels makes him think that now he’s different, when that’s not the case? If I say something to the other two, will they lose that comfort with their bodies that I’m happy they have? And now I’m in a spiral of parental doubt.

A: A few thoughts, in no particular order: You are probably not a prude. Your kids sound great. Having a “pants on” rule in the house is not excessive. Which leads me to my official ruling: Don’t ask your stepson if he’s uncomfortable with his brothers’ periodic shirtlessness. Since he’s never mentioned anything about it to you, it would put him in a difficult position of possibly acknowledging to his stepmother the fact that he has ever noticed anyone’s state of undress, something no teenage boy wants to do, no matter how cool and understanding the stepmother. If, at some point, you changed that rule to “pants in all stories of the house, unless you’re in your room or the bathroom,” it would not destroy your sons’ body confidence. They would just wear more pants in the house (or spend more time pantsless in their rooms). This would temper justice with mercy. Pants for everyone.

Q. Can’t give anything up: My husband and I have been happily married for three years and have a wonderful little girl. When we moved in together, he had a difficult time consolidating his possessions—I ended up giving up at least five times as much as he did—and we lived in an almost exact replica of his old grad student apartment our first year of marriage. While I’ve let it go, it still creeps up, particularly when it comes to our knife set. We had two, and it was one of the only things I insisted on keeping because my knives are very expensive and were a gift to myself because I enjoy cooking. I acquired them before we even started dating. He donated his knives but has never seemed to let it go, taking every chance he can to try to convince me my knives are breaking—they aren’t. It’s gotten to the point that I’m afraid to throw away broken plastic soap dispensers because he might have an emotional attachment to them. What should I say to him?

A: If that’s not a comical exaggeration of the situation and you’re genuinely concerned your husband would be emotionally distressed by throwing away soap dispensers, I think cognitive-behavioral therapy would help him treat his hoarding tendencies. This is not a cute, light-hearted squabble over whose knife set was better. This is about helping someone you love deal with a painful, compulsive anxiety over the state of his possessions.

Q. Unhappy fly on the wall: I volunteer at a small affiliate of a well-known not-for-profit in a small town. This organization is important to me. I adore the work, mission, and employees, but I take issue with the executive director. She’s abrasive and rude to the employees. She condescends, micromanages, and snaps. It makes me very uncomfortable to hear her speak to people. I come from a corporate background and know that outside of this situation such behavior wouldn’t fly. She means well, and I don’t think she knows how she sounds. Do I speak to the board of directors or stay out of it? I don’t want to hurt her, but I feel the organization could flourish under the leadership of someone with better interpersonal and management skills.

A: I’m not sure if your being a volunteer means it’s not your place to speak to the board about the director’s personality or if it puts you in a unique position of being able to advocate for her presumably beleaguered employees. I’m inclined toward the former, unfortunately. Since this isn’t behavior that’s directed at you, it will be a little trickier to pass along secondhand mismanagement. I certainly can’t imagine your continuing to volunteer there after telling the board you think it should replace its executive director, so think carefully about how this might backfire.

Q. Friendly co-workers, unfriendly dad: I’m a law student who was been working at a midsize law firm since last summer and will work there full time after I graduate. The atmosphere is very friendly, and the firm respects and values family time. I’ll be getting married about seven months after I’ve started full time, and my co-workers already love asking about me and my wedding. The problem is that I never had a good relationship with my dad growing up, and I cut contact when he became a severe alcoholic. It’s been three to four years since we’ve even spoken, and although he’s sober now, he just isn’t a good person, and I have no desire to be in contact. I’m dreading the point when my co-workers ask me about my family or who is walking me down the aisle. I don’t want to lie, but I don’t want to start spilling family drama and make people feel awkward. What should I say?

A: “We haven’t decided that part yet! I’m not sure if I’m going to do the traditional walk-down-the-aisle thing. But I’m really excited about the band we just found/caterer we’re working with/shoes I just bought.” Keep it light; change the subject. If someone asks you about your father in particular (I hope your co-workers are not in the habit of investigating your family relationships and are just asking out of friendliness), you can always say, “We’re not especially close,” and then move on.

Q. Checking him out, checking her out: This weekend I was rendezvousing with my boyfriend downtown. We had parked in two separate locations and were walking toward each other. I finally saw him up ahead, and we stopped on either side of the street, waiting for the light to change. I saw him strike a flirtatious pose and start posturing, and I laughed—this is a game we play a lot, where he flirts with me from across the room by posing and pretending not to see me. Except, I realized … he didn’t see me! He was posing for the woman a few feet to my left. When he saw me he visibly started, and when he crossed the street he made a guilty comment about how he wasn’t checking anyone out. At the time, I shrugged it off, but my irritation has been growing over the past few days. We’ve been through a bit of a rough patch recently involving his interest early in the relationship in leaving me for another friend, which I recently discovered.

What is your ruling on significant others checking others out in public—is it behavior that I could rightfully comment on, or just a natural part of being with a human being who has eyes?

A: One of the joys of adulthood is that learning that you get to say, “This bothered/hurt me” about anything that bothered or hurt you. There is no behavior you do not have the right to comment on, as long as you do so honestly and respectfully. I don’t have a one-size-fits-all policy on public flirtation, but I think it’s perfectly appropriate to tell your boyfriend, “I’ve felt insecure in the past because of your flirting (cheating?), and it was painful to watch you flirt with someone else when I thought you were trying to flirt with me.” You’re not telling him he’s a bad or untrustworthy person or demanding that he never register attraction for another human being again—you’re just telling him how you felt. Give him the opportunity to do right by you. If he brushes you off or tries to make you feel foolish for being insecure, he might not be someone you want to trust with your feelings.

Daniel Mallory Ortberg: Thanks, everyone! Don’t date co-workers, probably, but if you do, maybe it will be incredible? Let me know if you’ve dated someone at work and things worked out. Until next week!

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