Have you seen the movie "Secretary"? Yeah, like that.

June 19, 2012 6:53 AM

Asking for a Friend/CoWorker: Boss and underling develop feelings for each. Both break it off, but now friend is feeling hurt and rejected. What advice can I give her?

My friend works at the same law firm as me, and has put herself in an awkward position. Over the past few months she had been very friendly with her boss and over the recent weeks it had turned into overtly flirting. She says she doesn’t have feelings for her boss, but that there was strong tension between them.
I don’t know the full story, but over the weekend she had decided enough was enough after a lawyer caught them chatting (she insists nothing physical happened between them, but there was lots of texting and their topics of conversation crossed over the professional line).

I assume her boss felt the same way, because he started acting cold towards her this week. On the one hand she tells me she’s okay with this but is saddened by his lack of emotion towards her. I suspect she started to develop feelings for him, as he most likely did her.

Now she’s coming to me for advice. She understands the need to be professional (for both of their jobs), but she feels having him distant and stand offish will make her just as upset. She makes a good wage and has friends(me!) at this job but feels like leaving if it’s going to be like this.

I asked her if she wanted to sleep with him and she stated no, but she seems confused and most definitely hurt. What should I tell her?

My opinion is to stick with it - I understand that flirting happens, but I think she's taking it too personally. I know this lawyer and he is married and seems happily so. BUT -- I know what it's like to fall for someone and I'd like to tell her more then "Suck it up".

posted by Danithegirl to human relations (19 answers total)

Is this her direct boss, or someone who is part of a group of people she reports to? Can she distance herself from this person for awhile, either by taking on projects that don't directly report to him, or using a middleman to communicate between them, or transferring to another department/team for awhile?

I think you're right that it'll dissipate in the long run, but immediate feelings can be raw and difficult with constant interaction. If there's a way she can continue at work without having to be in constant contact with this person, I think she'll most likely be okay with some time.
posted by xingcat at 7:05 AM on June 19, 2012

The relationship they had, with texting and flirting was inappropriate. If she can move to a different attorney in the firm, then so much the better. If not, it may be a good idea for her to move onto a different firm and to have learned a lesson.

When a boss/subordinate have crossed a line and have become inappropriately intimate, it's hard to unring the bell. The boss in this case has become neutral and cold, which is probably the correct response for him. She's got hurt feelings, because her buddy isn't all friendly and flirty with her. What is this? High school?

Your friend needs to understand boundaries, in work situations and with married men. His behavior is inexcusable, hers isn't all that smart.

I don't think this relationship can be anything but awkward at best or antagonistic at worst going forward.
posted by Ruthless Bunny at 7:06 AM on June 19, 2012 [1 favorite]

I think that it might be a bad idea for your friend to assume that her boss returned his feelings. It is entirely possible, especially if this guy is happily married, that he's been flirting innocently because that's just the kind of guy he is, and someone had a conversation with him. "Hey, do you know X underling seems to be developing feelings for you?" Or, "Hey, you know, it almost looked to me like you were flirting with X!" In that case, the response would and should be, "Whoa, no! I'll cool it down so she doesn't get the wrong impression."

Try suggesting (gently) that she may have misinterpreted the situation, and that she shouldn't interpret his new behavior as a slight.
posted by corb at 7:16 AM on June 19, 2012 [1 favorite]

Tell her he's protecting both their jobs.
posted by chesty_a_arthur at 7:17 AM on June 19, 2012 [14 favorites]

She might have wanted to sleep with him but not wanted to admit it to you (or to herself), or might have liked the attention even while aware that it was potentially coming from a place she would not have been comfortable with. None of this makes her, or him, a bad person as such, because it sounds like they hit some kind of a hard boundary and the boundary stuck. That's good. Honestly, it sounds like this outcome was probably one of the better outcomes that could have happened. Perhaps, in time, she can appreciate that. This was the good outcome.*

And, perhaps she could treat this a little like a breakup -- although that would probably require her to acknowledge it as an actual loss that she's suffered. She misses being flirted with by someone who used to enjoyably flirt with her and is now (perhaps pointedly) not doing that. Sure. That's a thing that you might miss. She might even (totally irrationally but still understandably) feel a little bit rejected by her boss.

So what do you do after a break up? You start the hobby you've been meaning to take up. You get plenty of exercise. You start volunteering. You do things to get out there and to take your mind off of the loss.

This will be difficult for her because she has to work with the person all the while, but ultimately she can be professional and treat her professional work relationships as though they were all about getting the work done. It's not personal. It's work. She needs to understand that realistically there wasn't much else that her boss could do without putting at risk his marriage (probably) and both of their jobs (almost certainly).

* The best outcome would have been for them to have better respected some of the soft boundaries around keeping work and personal life separate, but since they didn't do that, it's good that the hard boundary did it's job.
posted by gauche at 7:23 AM on June 19, 2012 [1 favorite]

It's never easy when someone who was once warm and friendly towards you suddenly starts acting cold and distant. But as Chesty says above, he's trying to protect both their jobs. Your friend needs to remind herself constantly that this is the case, and that regardless of her internal emotional reaction, she needs to act absolutely professional for both their sakes as well.
posted by LN at 7:25 AM on June 19, 2012 [1 favorite]

Sounds like the boss is doing the right thing and pulling back before things got too out of hand. It's easy for friendly flirting to go too far. Personally I suspect if the boss didn't like (not LIKE like but like) and respect your friend he would feel a lot less compulsion to become so obviously cold and keep the distance, he is trying to return things to a professional level for both their sakes.

Your friend got of easy a lot of bosses might not have respected themselves or their underlings to stop at this point and taken advantage of an easy target.

I imagine the extra cold behaviour will relax a little, though not to previous flirting levels, once he sees that she is now going to respect his new boundaries and act professionally, but at the moment I suspect he is trying to make it extra clear to her where the line is.
posted by wwax at 7:29 AM on June 19, 2012

Thank you for the great answers. She does work with him directly, so avoiding him doesn't really help.

I think I will tell her he's doing it to protect her. Whether or not that's true, I think it would be the nicest way to tell her. Clearly, he likes her as professional or else she would've been given walking orders.

The advice I'll give her is to treat it like a break up. I understand it must be difficult for her going through this (I've had my fair share of rejection - not that this is like that, but similar). If she does feel like the professional relationship can not be mended, then maybe she should look for another job.

It's a tough cookie since I love working with her. I guess the next piece of advice is NOT to flirt with your boss (married or otherwise!)
posted by Danithegirl at 8:02 AM on June 19, 2012

It depends on her actual role and firm prospects.

Not to be overly practical, and maybe a bit of a jerk, but if she is a junior lawyer she may find this coldness is the start of being frozen off the promotional ladder. If she is support staff, fear of a sexual harrassment complaint may mean her job is more or less safe. Judgment plays a different role depending on the actual position in a law firm and hers has been admittedly poor. It is not just about feelings.

This aside. Right now she needs to get her feelings under control however she can and you can help her by explaining that his response as a married guy in a professional setting is supremely rational and not insulting.
posted by skermunkil at 8:06 AM on June 19, 2012 [2 favorites]

I guess the next piece of advice is NOT to flirt with your boss (married or otherwise!)

Especially if her next boss is at the same firm or if the legal community is small and gossipy (it probably is). A one-off flirty thing is something she can overcome. Twice, in the super-risk-averse-and-lawsuit-wary world of law firm management, is enough of a pattern as to pose a professional problem for her in the future.
posted by gauche at 8:30 AM on June 19, 2012 [2 favorites]

What are YOU getting out of this situation? Because what you've described is not really even similar to the summary above the fold--rather, your work friend has been acting inappropriately enough with her married boss that someone has had to intervene, and now she is upset enough about this to threaten to quit. And that's from her side of the story! It may be cold but I'd advise YOU to take a long hard think about the possible ways (from somewhat messy to truly nasty, as alluded to by shermunkil) this could play out and think about what the consequences are for you as her confidante/ally. It may be juicy but this is not drama that you want your career to be involved in even peripherally.
posted by animalrainbow at 8:31 AM on June 19, 2012 [1 favorite]

I am going to go in a slightly different direction. I think treating it as a breakup or framing it as something he is doing to protect her puts a fairly rose-tinted-glasses view on a situation that may not be fair. It almost justifies the boundary-crossing by suggesting that he shared her feelings and if only for this damned job, they'd be together! It also fuels romanticizing the situation.

I think it might be more helpful for her to take a more proactive approach or framing to this situation. What is SHE going to do that protects her career from potential damage? What kind of boundaries will SHE enforce to ensure that this doesn't happen again? How can SHE get out there and start meeting people who are in a position to reciprocate her advances without jeopardizing job/reputation?
posted by sm1tten at 8:59 AM on June 19, 2012 [1 favorite]

I don't think I would consider myself an "ally" - and I didn't even realize anything was going on until she told me yesterday. I've kept neutral and listened like a friend has, but not offered any advice other than it was an awkward situation. Selfishly, I would like to have my friend stay, but realistically, if she feels she has to leave, I would support her.

My honest opinion is that it was stupid, but that these things do happen and she should move on, but I can tell that she's distraught over the situation. I have never been in this situation, so I'm looking for some constructive advice to give her as oppose to putting her down or making her feel any worse.
posted by Danithegirl at 9:22 AM on June 19, 2012

I am going to go in a slightly different direction. I think treating it as a breakup or framing it as something he is doing to protect her puts a fairly rose-tinted-glasses view on a situation that may not be fair. It almost justifies the boundary-crossing by suggesting that he shared her feelings and if only for this damned job, they'd be together! It also fuels romanticizing the situation.

Even though I'm the one who said "treat it like a breakup" I totally agree with this advice. I more meant, "be deliberate about moving on with your life without this person" than "moon around about how it could have been different if only." Just want to make that clear.
posted by gauche at 9:29 AM on June 19, 2012

"be deliberate about moving on with your life without this person" than "moon around about how it could have been different if only." Just want to make that clear.

That's how I interpret it. I want to tell her that its done - move on, don't look back. To handle her feels like one would after a break up.
posted by Danithegirl at 9:32 AM on June 19, 2012

I actually think that telling her that flirting with bosses is a horrible idea is really constructive advice. Because if she keeps this up it will fuck her career up and tie up her romantic energies, perhaps to the point where it will keep her from getting out there and looking for actually available men.
posted by Sidhedevil at 9:39 AM on June 19, 2012 [1 favorite]

Tell her to consider herself incredibly lucky and take this as a warning not to do it again. Not so much the workplace flirtation, because a lot of legitimate relationships do start at work. It's the workplace plus the guy being senior and married. It's just the road to disaster on a career and personal level. In her case there is another layer, which is that it was a fantasy relationship. If the language about "they both" is hers, well, there was no "they both." She needs to get out there and have real relationships. Assuming a relationship is something she wants.

Especially if her next boss is at the same firm or if the legal community is small and gossipy (it probably is). A one-off flirty thing is something she can overcome. Twice, in the super-risk-averse-and-lawsuit-wary world of law firm management, is enough of a pattern as to pose a professional problem for her in the future.

Yep. Einmal ist keinmal, zweimal ist immer. She's had her one strike; after another one people will start saying she's making a career out of this.
posted by BibiRose at 9:43 AM on June 19, 2012 [2 favorites]

Your friend should, upon waking each morning, say a silent "thank you" to the cosmos for having dodged a BIG bullet. Cooler heads prevailed and much more awkwardness was avoided. She needs to Let. It. Go. and be grateful.
posted by thinkpiece at 9:55 AM on June 19, 2012 [3 favorites]

Seconding what thinkpiece said. Once upon a time I was a boss (incidentally also in legal profession) who had crossed the line from flirting to emotional relationship with secretary. Some weeks later I, an avowed atheist, started praying to God that this relationship turn to simple platonic friendship immediately. I wish now that I had the guts of her boss and stopped this when I could.
posted by przepla at 10:17 AM on June 19, 2012