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All Your Questions About Dating a Co-worker, Answered

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The Cut’s “Ask a Boss” columnist Alison Green tackles your questions on the particularly complicated matter of office relationships and dating your co-workers. What do you do if you think your boss is having an affair with your co-worker? Can you ask an old date for a referral? Find those answers and more, ahead.

Should I tell my co-worker I have a crush on her?

I started a new job at a small nonprofit seven months ago. About five months into the job, I realized I had developed feelings for one of my co-workers. As in, I think about her all of the time and I can’t wait to get to work each day just so I can see her. I think the feelings are mutual, but I can’t be certain because we’ve never spoken directly about it, and we’ve been very professional up to this point.

I don’t want to put her in an uncomfortable position, especially if I’m wrong about her returning my feelings. On the other hand, I feel like I will regret it forever if I don’t ask her out, or at least talk to her about how I feel.

We don’t really have an HR department, and I haven’t been able to find a policy listed anywhere that addresses workplace relationships. Is it selfish to broach this subject with my co-worker? Or should I try and find a different job, and then ask? I am willing to do that if that’s what it takes.

Don’t tell her you have a crush on her. Since things have been strictly professional between the two of you, blindsiding her with a declaration of feelings is a recipe for awkwardness all around. You have to continue working each other, and it’s not fair to introduce that potential for discomfort into her daily work environment.

But what you can do is make a few warm, friendly overtures to try to get to know her better, and pay attention to see if they’re reciprocated. If they are, you can ask her to hang out outside of work sometime. But that part about reciprocation and paying attention to her cues really matters. If you don’t see those things, that means you’ll need to back off. This is pretty much always the case when you’re interested in someone but it’s especially true at work, since she’s a captive audience and you have an obligation not to make work weird for her.

As for leaving your job and then asking her out, that’s a pretty extreme move when you have no signs thus far that she’d say yes … and it puts an awful lot of unfair pressure on her. Stick with the lower-key strategy above.

My boss is having an inappropriate relationship with a terrible employee.

I am a manager. My own manager has four direct reports, all managers. He has developed a close friendship with one of the managers, Jane, who reports to him. They are both married. They spend most of each day alone with each other in one or the other’s office. They work out together and lunch with each other almost every day. They frequently travel together for domestic and international work travel.

This has created an environment in which the rest of us don’t trust our boss or our peer because of the relationship. It has fostered suspicion among my peers that our compensation is impacted by this relationship. It has also created difficulties because most of our reports believe their relationship is romantic.

Complicating matters, I also believe Jane to be the least effective people manager. Her team is a revolving door and those with tenure resent her and my manager. We have discussed this with my manager and he seems unconcerned about the problems.

I’m not comfortable taking this up a level above him for fear of repercussions. Experience tells me this stuff works itself out. But it hasn’t. What in the hell do I/we do?

Yeah, even if your boss and Jane aren’t actually having an affair, they’re behaving so intimately with each other that of course people will worry about favoritism and bias. Throw in that your boss has shown that he’s not willing to act on problems with Jane, and it gets worse. This is exactly why companies generally prohibit dating in your chain of command; even if there isn’t any actual favoritism going on, it’s sure as hell going to look like there is.

But if you’re not comfortable escalating this to someone above your boss, you don’t have many options. Someone from above needs to intervene, and it’s not something you have standing to do on your own. However, if you tip off someone above him, you can be explicit that you’re concerned about repercussions and ask that the person do their own observation and be discreet about where the initial information came from. That’s not always something a company can honor, but in a case like this they should be able to.

Can I ask a past date to refer me for a job opening?

My fiancé and I have considered moving to the Bay Area. In my search I found one job opportunity in particular that greatly interests me, and while navigating their website found out someone I had met about four years ago now works as the company’s chief officer.

We met while our agencies were working on a mutual project and when that ended he asked me out for lunch a couple of times. He was a gentleman and was very respectful, which I appreciated, but there was no connection. Neither of us pursued it further.

Would it be inappropriate to send him an email just to inform him I have applied for a position at his company? I know I have less of a chance of the hiring manager looking at my résumé because I am not a local and would be relocating.

If you hadn’t worked together before those lunch dates, the connection would be too tenuous to be useful. But you have an actual professional connection from working on a project together previously, so I think you can mention it to him like you would with any other professional connection.

By the way, don’t just say you’re letting him know you’ve applied, since he may just think “okay, cool” and move on. Be direct about what you’re hoping for: “I hoped you might mention my application to the hiring manager if you think I might be a good match for the role.”

My company wants to ban workplace dating.

I started working with my current employer as a receptionist and developed a fairly close friendship with a colleague which slowly developed into a romantic relationship. We spent approximately one month debating about whether or not it was appropriate and finally decided that it wouldn’t hurt anyone.

I am now working as the HR manager, with no direct reports, and my general manager has informed me that they want a policy to be put in place saying that managers cannot date any employee, even those who don’t report to them. My relationship with my boyfriend was not against company rules when it started or when I became a manager, so I didn’t see the need to tell anyone. Am I now obligated to tell my boss the situation, and can he fire me for it?

Yeah, you need to tell him. He’s asking you to implement a policy that you yourself are in violation of, so it would be really odd if you didn’t speak up. And for what it’s worth, you might have erred by not speaking up earlier. Even though you don’t manage your boyfriend, it’s pretty common for it to be considered inappropriate for an HR manager to date anyone in the company because of potential conflicts of interest; after all, you might be involved in your boyfriend’s compensation or in navigating other issues where you could understandably be perceived as biased.

In theory, your employer could fire you if you refuse to comply with the policy, but it’s more likely that the worst-case scenario is that they’ll say that one of you has to find another job (and give you a bit of time to do it). It’s also possible that you can negotiate to have the relationship grandfathered in, but you’d need to be transparent about recusing yourself from any HR matters concerning your boyfriend.

Was I wrong to assume my boyfriend could come to a company dinner?

I have been with my company for almost three years, and this will be my third time attending a trip with the company. During this trip in past years, many of my co-workers’ husbands/wives have come along (staying in the spouse’s hotel room). Co-workers whose partners accompanied them on the trip brought their partners to the company dinner held on the first night of the trip. The company even refers to this dinner as “the annual family dinner” (partners do not attend other dinners during the trip). 

Given all this, I assumed that it was no issue for my long-term boyfriend to stay in the hotel while I was there and attend the dinner. But a few days ago, my boss’s boss sent me an email with my hotel info and my dinner itinerary for the trip. I replied to the email, thanking them for the info, and also added a note that I was planning to have my partner accompany me to the “family dinner.”

Yesterday, I received an unexpected email from my boss, correcting me for improper conduct. Apparently I was wrong in assuming it was fine for my boyfriend to join me. My boss communicated that his boss was upset and felt like it was disrespectful of me. 

Was it completely wrong for me to assume that it was okay for him to join me? I travel a fair amount for my job, but this is the only trip I have even considered bringing my partner along with me since it seems to be socially acceptable for the rest of the company. Do you think that there’s a possibility that it’s an issue because my partner and I are not married? Do you think that the biggest issue is that I assumed that it would be okay and didn’t ask? 

It can feel quaint, but some employers do still make a distinction between spouses and non-spouse partners for work events like this. You generally see it at older, stodgier companies. Any chance that yours fits that description?

But if your company’s tradition has been spouses only, they should have just explained that to you, not chastised you for not knowing. It wasn’t “disrespectful” or presumptuous of you to see other long-term partners attending and not realize that marriage licenses were required.

Can I recommend my partner for a job?

My significant other just lost his job somewhat unexpectedly. He has applied for a similar position at a local company. As it happens, I am the chair of the board of a nonprofit and one of my fellow board members is an executive at this company. Would it be poor form for me to mention to this person that my S.O. has applied for a job there? If it is useful to know, I haven’t known this person long (less that a year), but it is an informal board and we have had a chance to socialize and become friendly. We can’t tell at all if this position my S.O. is applying for would be reporting to my friend. I’d hate for there to be any implication of asking for a favor. 

The trick with recommending a significant other is that you need to be clear that you’re not pressuring anyone to give him special consideration and that you won’t be offended if they end up thinking he isn’t the right candidate for the job. Otherwise you can leave the person feeling obligated to interview your partner even if they otherwise wouldn’t have, and worrying about awkwardness if they have to reject him.

But it’s fine to say something like this: “I wanted to give you a heads-up that my partner, Colin Featherton, applied for your communications role and he has pretty interesting experience on the merger issues that you’re tackling now. But I know you’ll have lots of candidates, so no pressure from me to interview him if he’s not what you’re looking for!”

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All Your Questions About Dating a Co-worker, Answered