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Dear Prudence: Help! Does My Workplace Crush Mean I’m Gay?

Q: Does having a crush on my mentor make me gay? I love my work and am part of an amazing team of people. It took me years to find a place where I fit in and feel accepted, and this job has been the most professionally satisfying of my life. One of our colleagues has always impressed me, he’s in a senior, very prestigious role, has an Ivy League degree, and is one of the best in his field. I’ve admired him since I started working alongside him, even as a subordinate. Eventually I got to be mentored by him, which helped me pass my night school classes and get qualified in the same field. I even started buying nicer suits, because he’s always so well-dressed. Some of my teammates noticed this and began cracking jokes about my “crush” on him, which I just laughed off, but deep down it worried me.

I always thought I was straight because I grew up believing that there were only straight people and that gay people had just lost their way from God. Now I’m older and I know more gay people, and I know that sexuality and God are way more complicated. But I don’t know if this means that I am gay. I have never felt like this towards a woman, only men, with guys I admired at school and at college, but I didn’t hit on anyone (at school I would’ve got my ass kicked for even looking at a guy weird) and focused on girls. I do like girls, but it feels different than this. I tried to stop thinking about him and seeing less of him at work, but that’s hard for obvious reasons. Plus, I miss our talks. Even though he makes fun of me sometimes I don’t think he dislikes me, but I don’t know if that means anything. Is gaydar a real thing? Can he tell that I like him back? I tried dating more women but that didn’t stop the thoughts.

A: There’s no way to tell if this is just a crush or something more significant, but it’s inappropriate to use a professional relationship as some kind of acid test for being gay or bisexual. Your colleague helped you out as a mentor and didn’t hit on you, which sounds like he is maintaining a professional distance. Relationships at work are minefields for many reasons, but in the case of someone who is senior to you it’s particularly hard not to cross important lines. Whether or not “gaydar” is a real thing, there’s nothing wrong with keeping your distance from someone who inadvertently detonates an emotional landmine in the middle of your working day. Crushes fade with time, but if this is affecting your work life you need to manage it before crossing any boundaries. Instead of betting on his telepathic abilities or dating women you’re not interested in, take your feelings to a professional counsellor or therapist and work through them in a safe environment outside of work.


This Week in Savage Love: Apps and Avoidance

Dear Dan,

My co-worker and I get on really well, even though he hit on me once (I’m a straight woman) and I turned him down flat. He didn’t take long to realise that it was a titanically stupid move on his part, and now we’re good friends. Lately he’s been doing this thing where he makes a big deal of showing me something on his iPhone by scrolling through his apps, and there’s Grindr, Scruff, Chappy, the full meal deal of gay hook-up options. If he’s just enjoying seeing all the penises in a five mile radius, I’m happy for him. I’d be down for getting a drink and comparing my collection of unsolicited nudes from Tinder with whatever thirst traps he’s bagged. But when we go to the bar and I try to bring up a related subject, like Bye, Felipe or dick pics, he looks freaked out and changes the subject. I’m not sure if he wants to come out or if he’s just peering through the closet door, but frankly he's insulting my intelligence if he thinks I wouldn’t pick up on a thumbnail called Guy Spy.

Won’t Ignore Notable Gay When Only Male Apps Noticed

Dear WINGWOMAN,

This dude sounds like he’s working up to coming out, but while he can tap all day on the apps, he’s got to stop using his phone in place of his words. Next time he does the trick with his overflowing screen (and I hope he’s on a decent plan, because those things chew up data), feel free to ask him what’s up with all the cockbaiting clickbait he’s downloaded. Then offer to take him to an actual gay bar where humans, not avatars, hang out. But make him buy all your drinks.


Dear Abby: I Spied On My Brother’s Phone - Can I Still Set Him Up With My Friend?

Dear Abby,

I’m worried about my brother. He has a really stressful job, but he’s always been such a sweet, heartfelt guy, and he always showed up for our family dinners, birthday parties, graduations - he even catered two baby showers. But one time I went snooping on his phone, trying to find out what had happened with his ex-girlfriend, and I found all these intimate messages - to another man. I pretended that I hadn’t seen anything, and he never said a word. We’re from a quite conservative background, though it hurt that he didn’t want to talk to me about it. But I have a friend, “Mary”, who my brother once told me he had a crush on, back when she was in a relationship. Recently she broke up with her loser boyfriend and now she keeps bugging me to set her up - with my brother. Years ago I got drunk and blabbed to her that he said she was cute, so she thinks he’s interested. I don’t know what to say to her. I can’t say that I think he might be gay, but I also don’t want to be in the way of them getting together, because they would be a perfect match. My other sisters think we should have a dinner and invite them both along, but I keep putting them off. What should I do?

Signed, No Straight Answer

Dear NSA,

You’ve learned a good lesson - never “snoop” because you may not like what you find. You don’t know the full story behind those messages, and you don’t know whether your brother is gay, straight, or bisexual, but you do know that you broke his trust in you. You also got drunk and told “Mary” something he said to you in private. Now Mary, and your sisters, believe one version of the truth, while your poor brother has no idea what’s being said behind his back. If you want to be a good sister to your “sweet” brother, start by being honest with him. Ask whether he’s still interested in Mary, and if he’s not, let her know gently. Put your suspicions about his sexuality behind you, and stop trying to interfere in other people’s love lives.


Hola Papi! Should I Let Down the Co-Worker I Had a One Night Stand With?

Hola Papi!

I could never resist lightly flirting with a guy at work, despite (because?) of his reputation as being a straight bro with a big side order of Catholic guilt. I’m a recovering Catholic, too, so maybe that was it - and he always came back with whatever I said with some smartass remark. I never thought anything would come out of it except a friendship, but then he stopped going out of his way to talk with me, so I figured I’d triggered some sort of no-homo panic and left him alone. Then, after a really rough week, we ended up getting good and drunk together with the rest of the team. It was like old times, but I was still surprised when he offered to split an Uber with me then in the backseat, stuck his tongue down my throat and his hand between my legs. Not that I was complaining - I ended up going around to his that night.

It was better than I’d even imagined, and we both said some stuff in the heat of the moment. Now he’s blowing up my phone, asking if we can hook up again. When I manage to engage my brain cells, I ignore the messages, but in weak moments I hit him back, not confirming or denying but letting him twist in the wind. I don’t feel too bad about it, he did the same to me after all, but I also can’t stop thinking about him. Obviously, sleeping with him again is a terrible idea, but how terrible is it?

Signed,

Not His Papi (...Yet?)

Hi, Not!

That question mark at the end of your sign-off is screaming louder than Jennifer Lawrence in mother! Is pursuing this guy a terrible idea? Maybe, maybe not, but you know what is a terrible idea - like, releasing live butterflies during a lip sync level terrible - stringing this poor bro along when all he wants is to know where he stands with you. Or kneels, as the case may be. If he was confused about his sexuality for a while, that’s no crime, and doesn’t merit something as petty and downright cruel as toying with him in some weird vindictive power play. Make like prime-era Backstreet Boys and quit playing games with his heart.


Funbag! What’s the Best Birthday Present for a Fuck Buddy?

After a few drinks at work, I ended up in bed with a colleague that I’d had what I used to think of as a “straight man crush” on. Well, gay sex turned out to be way more fun than I’d been led to believe, and now we meet up once or twice a week. It’s good - really good - but it’s been a few months and I feel like I should do something to acknowledge that this isn’t just an awkward one-night-stand anymore. His birthday is coming up, and I wanted to get him some kind of gift, but this guy literally has everything he could want and his taste is kind of out of my price range, anyway. What do you get for the guy who has everything? A Starbucks gift card isn’t going to cut it.

Why not a Starbucks gift card? Nothing says ‘thanks for the great shag' like a Unicorn Frappuccino. Nice work squeezing in a humblebrag about having amazing sex, by the way. But the etiquette dilemma about what to get the guy who’s providing the top tier orgasms in your life has already been solved by Beyoncé, who said “When he fuck me good, I take his ass to Red Lobster.” Invite him out for dinner, tell him it’s on you, and let him order an extra serving of cheddar biscuits. Get him a really nice bottle of hooch as well. Food and booze were invented to save people from having to have long conversations about how much they like each other before sex.


Ask a Manager: Is a congratulations card suitable for my private boss?

A reader writes:

I’m a legal secretary, and my boss is getting married in a month’s time. I couldn’t be happier for him. I know his fiancé, too, because we all work together, but in different departments. His fiancé’s team is going all-out on pre-wedding celebrations, with a surprise shower last week, cakes left on his desk, and many, many celebratory drinks. Whereas my boss is more reserved and, although we’ve worked together for years and I know he appreciates my work, we don’t really socialise. But I’d like to get him a card to pass on my congratulations. I know it’s not the same thing as a surprise shower, but we’re not really that kind of workplace. Would a card be overstepping the mark? We have never exchanged gifts before, but he is always extremely generous with giving me time off, extra training opportunities, and raises. (We don’t have to miss out on the cakes because his fiancé always drops off extra pieces that he’s saved for us).

A card is a lovely gesture! It sounds like the two of you have a very healthy working relationship, and acknowledging a joyful event in his life with a personal note is often more welcome than wading into the landmine of gifts at work. If you wanted to, you could also write another card for the fiancé who brings you cake - he sounds like a keeper.