I have a crush on my boss!

A TRUE GEM:

I'm writing to you because of a weird relationship I have with an old boss.

I worked for him as an intern (he was the head of the company) while I was in college. After I had stopped interning, I reached out and asked if there was any on-the-side work I could do for him. He said yes, and I did informal freelance work for him for the next few years (I still do, occasionally). 

Initially, our relationship was strictly job-oriented; he would give me a task and I would do it. But over the next few years, it became more of a mentor/mentee type thing; he's successful in the field I want to work in, and so I'd ask him for advice, references, connections, etc. He's always been super nice about that and extremely willing to send an email to someone telling them I'm great. And I have always harbored a hope that I'd end up actually working for him one day; he's said many times that he wants to eventually create a job for me at his company, and that if he could, he'd hire me now (although this has never panned out, so who knows how serious he is). I'm really grateful for his professional support, which has allowed me to do a ton of stuff I wouldn't have otherwise. 

The thing is that our relationship isn't solely professional. I have strong positive non-romantic feelings about him; he is supportive and kind and funny and a good friend and mentor. We've spent time together in non-work capacities––he has a big party every summer that he invites me and my boyfriend to, and has invited me to other events as well, non-worky things where he is often slightly to very drunk. Perhaps more importantly, I have a weird "you're my authority figure/boss/dad and I'm into it" crush on him. I've at times felt a romantic/sexual/flirty vibe from him as well: stuff like saying he loves me in emails or hugging me for slightly too long when he's drunk. His wife is also super cold to me, despite being very nice to everyone else I've seen interact with her.

Despite these vibes, nothing romantic/sexual has happened between us and hopefully it never will. Although he's a kind of chaotic person––disorganized and depressed and, imo, often drunker than I would choose to be were I a 40-something parent––I'm honestly more worried about my decision-making than his. How do I make sure I'm not acting inappropriately and pushing this often-great relationship over the line? 

I know that in this scenario I'm the less-powerful person in so many ways: young, female, unestablished in an industry that rewards personal connections. But I am also a responsible party here. I love to flirt (with him and everyone else), and I definitely toe the line by sending emails/texts that are way more casual and personal than ones I would send to any other boss I've ever had. Even parts of our professional relationship (how fast will he email me back about this assignment?) feel like I'm waiting for a text back from any other crush.

I want to make sure I'm not doing anything that would jeopardize this important professional relationship simply because I have a stupid crush. But I find this difficult because my personal and professional feelings about him are roughly inseparable. I want him to think I'm smart and capable and do good work both because he's my boss and because I have a crush on him.

How do I deal with my feelings in a relationship that's both professional and personal, and how do I make sure I'm not crossing any lines while still retaining the normal intimacy that makes a relationship with another person good in the first place?

SOPHIA:

There’s a lot going on here, which is what happens to your brain when you have a Big Dumb Crush on someone you shouldn’t: your brain muddles things so that what once was clear now seems unsolvable. It’s a brilliant way for your brain to get to spend more time thinking about its favorite thing: your crush!!!!! If only your brain can convince you that this is some fraught, complicated jam that it needs to Think Long and Hard About, then she can trick you into thinking about Him all day long.

I’ll get to what I think the “clear” answer is (from the outside, as a person who doesn’t have to do any of the actual hard work, of course), but let me say a couple things:

It is not stupid/cruel/bad/immature of you to have a crush on a mentor or boss. Or anyone! Even while in a relationship. In fact, it’s Incredibly Normal!!!!!!! So as you deal with this crush—which does need to be dealt with—please try to avoid punishing yourself for having the crush. And realize that you can’t stop crushes with your mind. Crushes are a bit like trains in that way. You cannot stop an Amtrak by will, but you can get off the tracks and out of the way of the oncoming train. Please, however, do not dwell in any small feelings you may have about having this crush. Power is hot. Being admired is hot. Being part of a team doing exiting work is as much of an aphrodisiac as I can imagine. It’s why everyone on Star Trek was fucking.

You say or hint a couple times— once outright—that you crush is not romantic. That is patently not true. You may not necessarily be thinking about the sex positions you’d like to engage in with Mentor Hunk, but lust alone does not equal romance. If someone simply said, “Think about your boyfriend,” I highly doubt you’d be thinking about the kinkiest, dirtiest sex thing you want to do to him. You’d probably think about a much more abstract way he makes you feel. How you two are together. That is the same thing you’re doing with your boss.

Ok, now, here is what I think you need to do going forward:

Firstly, I think you need to STRONGLY and PAINFULLY examine why it is/what you think it means that you’re a person who “love[s] to flirt.” I have said this about myself before, so it’s not like I don’t get where you’re coming from. But what I actually meant at the time I said it was, “I’m very desperate for romantic attention, especially from men because I see this as validation.” I do not know what it means for you, but what I do know is that harmless flirting is often only “harmless” for the person doing the flirting, rarely harmless for their partner or their flirtation-mark. People who are flirts invite a negation of boundaries on purpose because that’s thrilling for them. It’s exciting to you to see how much you can do without hurting your boyfriend. (This might not be how you’re framing it for yourself, but I encourage you to). The problem there is that you will hurt someone. You are playing Russian roulette right now with a relationship you seem to like and there is a reason behind that. Maybe you love excitement and fear death, and this makes you feel young and alive. Maybe because you haven’t figured out how to cope without external validation. I DO NOT KNOW, BUT YOU DO!!!!

(Caveat: maybe you and your boyfriend have spoken extensively about your flirting and it is a positive part of your relationship with solid boundaries. Maybe you have an open relationship. I don’t know, but once again you do. Please be honest with yourself about if flirting with other people serves you and your relationship).

This is not to say that you can’t/won’t/shouldn’t ever flirt with anyone again. FLIRTING IS VERY FUN AND OFTEN HARMLESS!!!! But the fact that you love flirting with other people and find yourself drawn to your boss to the point where his wife is cold to you is a concern. This is someone respected in your field and an important person in your life. It is time to redraw some boundaries, because right now you are being a Sloppy Sally!!!!!

Redrawing boundaries is effective because, like I said before, you cannot turn off a crush by telling yourself to. You have to wait it out and while you’re waiting you need one thing: STRONG BOUNDARIES. You don’t need to set out your new boundaries with your mentor, nor the reason they’re happening now. The boundaries are for you. Things like, “I’m not going to answer his emails as quickly and as informally any more.” While you can still be friendly to him, you have crossed the friendship line and your full-on-friendship privileges have been revoked for a bit. That means stop going to events with him outside of work. STOP. If you go to his party, bring your boyfriend and leave before too much alcohol has been consumed. Do not invite temptation and opportunity into your life at the same time!!!!! That is just fucking foolish!!! It’s like trying to eat less sugar but then baking yourself a cake and bringing a slice to bed with you. That would be fucking foolish, too!

While I’ve focused a bit on the personal repercussions of acting on this crush—even what you’re already doing!!—let’s not overlook the potential professional repercussions. Whether fair or not, the reputation as someone who flirts their way into a mentorship or who creates career opportunities via that avenue is not a good one. And it’s not as if no one has noticed. People pick up on stuff like that EASILY. I promise you, it is not just his wife who sees him hugging you a little too long. I promise. You are young and hardworking in an industry you seem to love—do not jeopardize it for someone you simply kind of like thinking about.

I’m sure you’ve both enjoyed your little flirtationship, you both need to STOP. It’s not appropriate. It’s certainly unkind to your partners to take up your time wondering what another person will think/say/like. It is romantic. It’s not helpful.

I know that life is very very unfair in that you only get to live it once; you don’t get to run a control and see what would happen if you lived life four or ten different ways. If you actually acted on your crush one drunken evening or if you didn’t. I’m sorry. It’s messed up that we only get one life. So let me do you a small favor and spoil how it would go if you were to ever act on your crush with him: dissatisfying. You don’t actually want him, you want him to want you. You want him to admire you. (He does, and lots of people will). Sex with him, kissing him, dating him, none of that would actually fulfill any need you have or bring you any closer to the imagined happiness you picture when you picture him. Fantasize all you want, but recognize that this fantasy would not be fun in real life. It’s like how when I was a kid I wanted a horse, but I never imagined myself actually shoveling shit, you know?

So. Take a few months to separate yourself and draw up new boundaries. Be gentle with yourself, you may have to mourn the fun you’ve been having having a crush. (Crushes are very energizing!) Use this time to think about how to add excitement, motivation and validation into your life that doesn’t come from men, bosses or mentors. It’s much much harder but so fucking worth it.




❤️❤️❤️NOTE: because so many sweetie pies have been asking questions, it can take up to a month or two to answer them. I’M SORRY. I try to answer “urgent” / timely letters ASAP and more general questions later. 

IF I HAVEN’T GOTTEN TO YOUR LETTER, PLEASE FEEL FREE TO RESEND!!! I DON’T MIND AT ALL!!!❤️❤️❤️


Sophia Benoit writes this very newsletter; she also writes about sex & relationships for GQ, tweets about everything else at @1followernodad, is a researcher for Lights Out With David Spade, and has had bylines in The Guardian, Reductress, Refinery29, Allure, and The Cut. You can reach her or yell at her at 1followernodad@substack.com.