Dear Businesslady: Advice on Workplace Crushes and Success -The Toast

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Email us questions at, subject line “businesslady.” Previous installments can be found here.

Dear Businesslady,

I am deeply, frustratingly, maddeningly in love with my female boss. I am also a woman, and I identify as “mostly straight” — I have only dated men but have had two other deep, frustrating, maddening, ultimately unrequited crushes on women.

My boss is five levels above me. She is one of the heads of our company. She knows how I feel, at least in a jokey sense, because our office is small and casual, and I am kind of … endearingly open about it? That sounds like I’m a freak, but I swear I’m funny and normal. She is friendly toward me, and even affectionate. She drives me home and we talk openly about our lives. But of course she is straight, and of course this is completely unrequited.

I don’t know how to get over it, and it’s making work very hard. I take her feedback very personally. I don’t mean to, but I am crazy about her and her opinions. I can’t leave my job because I love, love, love my job. How do you get over someone you see every day, who manages you, who is the world’s most beautiful and perfect person?

Frustrated in my Cube

Dear Frustrated,

I felt like I had to answer this since it feels like an inversion of the possibly-gay-boss query I fielded in my last column. But even though I took the opportunity to give that person a pretty extensive talking-to about appropriate workplace boundaries, the answer to their question was pretty simple, and the answer to yours is too:

You can’t date your boss.

This is true even if you and your boss are both single and mutually attracted to one another, although obviously that’s a pretty tempting scenario. And, okay, theoretically relationships can flourish between employees and their superiors, and I’m sure there’s plenty of anecdata about how Sometimes It Works and Is Totally Fine—but it’s more likely to be an unmitigated disaster for everyone involved (including the lovers’ coworkers), hence the rule.

If anything, your situation is easier to navigate because there’s no “do I quit my job and go for it?” hanging out there—your boss is straight, you’re both ladies, and it’s a relationship that seems destined to remain firmly lodged in the realm of the platonic.

I realize, though, that that’s technically not what you asked—you asked how to get over this “beautiful and perfect person” who also happens to be your manager. And before I address that question, let’s move on to your other letter, sent in tandem with this one (yep, it’s a twofer today, folks):


Dear Businesslady,

I am 27, working for [a workplace; specific field redacted to protect LW’s privacy]. I don’t know if I would have asked this when I was 22, because I didn’t think about my career or its trajectory as much then. You are in your early 30s. What would you say to your 27-year-old self about the next five years, and how to make the most of them professionally? I feel very much at a turning point in my working life, when success either starts to happen for you or doesn’t. Please help.

Hi again, Frustrated,

Maybe I’m reading too much into this, or am way off base, but I can’t help but feel like this second question is related to the one above.

I’m generally of the opinion that crushes reflect a lot more on the crush-er than they do on the crush-ee, and are mostly about what you’re projecting onto the object of your affection. I can’t tell you what causes them or how to make them go away, but every crush I’ve ever had—from pseudoplatonic, to dissonant with my typical attraction matrix, to actually fixated on someone who could be a viable partner—has existed almost entirely in my own head, as opposed to being in response to actual, real-world interactions. Since you mention that this unrequited-pining thing has happened to you before, and that you identify as “mostly straight”—and especially since your current crush is focused on your superior at a job you “love, love, love”—I suspect that it’s somehow tied to your feelings about your career.

I’ll let you sit with that presumptuous speculation for a second, because I’m also intrigued by your prompt of “What advice would you give your 27-year-old self about her professional development over the next five years?”

It just so happens that my 27th year was a pretty big one for me: I was feeling stuck in my job and was trying to figure out how to handle that when I got hit with a life-threatening illness. Once I recovered, those old frustrations were sharpened by my newfound perspective of “this is your only life and it could all end in an instant.” So even though some things about my old position were comfortable and convenient —and even though I could come up with countless excuses why it was a bad time for me to make a change—I decided to start exploring other options that were more in line with my personal goals, and that eventually led me to where I am today. Looking back, I wouldn’t change a thing, except that I would’ve maybe been a little more proactive about moving myself forward.

But at 27, I was in a job that I definitely didn’t view as a career. Even now—when I’m privileged to enjoy my work a lot more than most people—I probably wouldn’t say I “love, love, love” it, like you do. You’re living the dream! Yet you’re asking me for advice?!

Here’s the thing about career trajectories: they’re kind of impossible to predict. Sure, it’s productive to put some effort into thinking about your ideal five-year plan, but unless you’re in a field where there’s a clear hierarchy of consecutive positions, it’s unlikely that things will play out the way you anticipate. And like so many things in life, if you’re happy where you are, you’re already better off than almost everyone else on the planet.

Crushes are a similarly unknowable and mysterious force, but in my experience they tend to just slowly evaporate; like a canker sore that plagues you for weeks until the day you realize that your lip feels totally fine, you might see your boss one morning and realize that she’s just My Awesome Boss and not The Woman of My Dreams, If Only. It might help to focus on things that would undermine your long-term compatibility if you did get together—annoying habits she has, or disparities in music/TV/movie taste, schedule, food preferences, etc.—but it’s also probably good for you to double down on the work aspect of your relationship.

My 27-year-old self didn’t really have a mentor figure, but it sounds like your boss is pretty much the ideal: someone who’s senior to you in a job you adore, with whom you already have a friendly rapport. During one of these chats on the ride home from work, there’ll surely be an opening for you to say, “Hey, I feel like I’m on the cusp of a turning point in my career, and I really want to make the most of the next five years.Can you just, like, sit and just mentor me for a second?” Pick her brain about how she got to where she is, compare her position with your own interests and aspirations, and see where that leads. If nothing else, you have an amazing opportunity to gain some insights about your career. And maybe—just maybe—these conversations will help reinforce your respective roles as boss/employee, ultimately butting out the love-object/unrequited-piner dynamic that’s currently bothering you.

One last thing, though, before I go. I know what you’re saying about 27 being a crucial moment where “success starts to happen or it doesn’t”—but where you are at 27, 37, 47, whatever, isn’t necessarily an indicator of your big-picture happiness or prospective life achievements. The truth is that “success” is so subjective, and so arbitrarily defined within the context of particular groups, that it’s almost a meaningless metric. I make less money now than I used to but also have more flexibility in my schedule—does that make me more successful, or less? What about people who leave behind lucrative, even gratifying jobs to pursue passions that have little (if any) monetary reward—are they failures?

If you spend your days doing something you enjoy—and have enough capital at your disposal to not feel stressed by the demands of modern living—then you’re a success, period. Considering the position you’re already in, I don’t think you have much to worry about when you look to the future, and I expect that 32-year-old you will back me up on this someday. In many ways, yearning for the official status called “successful” is a lot like having an unattainable crush: a potentially useful tool for figuring out what you want (or don’t), but also a way of distracting yourself from the real (and realistic) opportunities available to you.

You’re earning money while not hating your life: that’s a gift. But it doesn’t have to happen at your current workplace indefinitely, and maybe the angst you’re feeling about your career is a sign that you’re ready for a change. If your love-love for your boss continues to interfere with your love for your job, do your emotional health a favor and start looking for a new position. I’m sure she’ll give you a great reference as you make the switch to a new workplace, and I’m equally sure that you’ll be a lot happier once you’re no longer feeling tortured by unrequited affection.


Businesslady is in her early 30s and somehow managed to find a rewarding career despite her allegedly useless degree in the humanities. Her job history includes everything from food service to retail to corporate nonsense, but she currently does writing and editing for a nonprofit, and devotes the rest of her life to playing video games, patronizing bars, and spending way too much time on the internet.

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