Should I be worried about my boss's intentions?

In My Humble Opinion
1

Here’s the background: I just started a new job about 6 weeks ago. I telecommute, and my boss lives in another state, so we chat daily (sometimes multiple times a day) over Skype, always IM or audio and never video. My boss is 15 years older than me, and has been married for about 25 years. I’m in my early 30s, single, and he knows that I am single.

A few times he has said or done things that have made me uncomfortable:

[ul]
[li] He greeted me over Skype with “hey beautiful how’s it going?” once, and I immediately told him that it made me uncomfortable. To his credit, he never did it again.[/li]
[li] The first time we met in person, he took me out to dinner at my hotel. At some point in the conversation, he mentioned that his wife had a round face, which he found pleasing, and then he said that I also have a round face like his wife.[/li]
[li] He gossips to me about the personal details of his other employees. One time he told me a female co-worker had kicked her husband out of the house after a big fight for being lazy and not finding a job, only to take him back a few weeks later.[/li]
[li] He tends to praise his wife when she comes up in the small talk we sometimes make on our Skype calls, but he has also divulged some very unflattering personal information about her. For example, he told me that she is having a hard time going through menopause, and that she freaks out almost daily and calls him with crazy rantings and ravings. [/li]
[li] Occassionally he sends me emails with news articles he thinks I should read, or that he thinks I will find interesting. Most of the time he sends these over the weekend, and I find it weird that a married man would be thinking of me enough to send me non-work related emails over the weekend…that’s never happened to me at any of the 3 previous places I’ve worked.[/li]
[li] On one Skype call where we were discussing ways to destress, he mentioned that he had relaxed the previous evening by running 10 miles at a 6-minute pace (he seemed to really want me to know he could run a 6-minute mile), then taking a long relaxing bubble bath with a bottle of nice wine.[/li]
[li] He tried weed for the first time last week and, while he was high, he sent me several emails about the transcendent effects of weed on the mind. The next day, he spent twenty minutes on our daily Skype audio status mtg telling me what a transformational experience it was, and he tried to make me promise to do weed with him next time I fly out for an in-person business trip. When I protested, he said he wouldn’t have mentioned it if he hadn’t thought of me as an open-minded person. (Note: weed is currently LEGAL where he lives, so he’s not breaking any laws.)[/li]
[li] He also told me he really wants to get his wife to try weed so that she will calm the heck down and not freak out so often.[/li][/ul]
So…I’m not sure what I should make of any of this. I’ve never telecommuted before, so I’m not sure if the lack of face-to-face contact (or even video contact) makes some people feel like confessing details of their personal lives? I should mention that other than the issues outlined above, my boss is a very easy person to get along with, and he is very encouraging and praises the work I’ve done so far. I really want to like him as a person (platonically, of course) but I just can’t shake the nagging feeling that his feelings towards me are more than platonic.

Is this guy hitting on me? Should I be worried? Anything I should do going forward to find out if he has unprofessional intentions towards me, or to protect myself? I really, really like my job, much better than any of my previous ones, and I really want things to work out at this new company. What should I do?

2

Sounds like a guy going through a mid-life crisis. The remote locations probably make it easier for him to overstep bounds, something common in e-relationships. Take a stick-to-business attitude. Don’t get involved in off-topic discussions. Also, make a record of any problems in conversation in case this turns into a bigger problem. I would find it hard to belief he isn’t aware that he’s stepping over the line, it sounds more like a cheesy come on by a guy with an itch. At best he’s temporarily lost his grip on reality and he’ll get over it soon. No matter what, don’t show any interest or participate in non-business oriented discussions.

3

Thanks, TriPolar. I definitely try not to engage when he starts talking personal details, but I also don’t want to run the risk of offending him. He definitely likes to have off-topic discussions with me, and most of the time they are harmless: economics, politics, music, etc. So I figure as long as I don’t encourage his overly personal tangents I should be ok.

I am more worried, though, about things escalating and me eventually having to turn him down, and then him getting upset and treating me badly at work or even finding an excuse to fire me…I’m sort of paranoid like that, I guess. At any rate, I am going to start recording our Skype calls and forwarding the questionable work emails to my personal email address, so if he tries something the next time I see him in person (or even on a call) I will have a trail of evidence!

4

Those sound like reasonable precautions.

I get the feeling he does have more in mind than your business relationship. I think it is appropriate for you to tell him if he makes you uncomfortable, if he comes on to you or the conversation gets too personal. Talking about politics or sports is a kind of casual conversation you might or might not feel comfortable talking with a coworker, gossiping maybe - though as your boss that seems a bit off. But you would be better served by stating directly that you like your job but would prefer to keep the conversations business related to avoid any confusion or possibility of someone else getting the wrong idea. That suggests your concern is as much perception by others as his possible intentions.

5

You should definitely be concerned. This is exactly how I’d be in that situation: unsure even though it would be very clear to anyone hearing about it. Dude wants you. Take that into account during all interactions.

6

I’m not very good at reading people, so I could be totally out in left field, but my first thought was that he finds the semi-anonymity of your telecommuting “relationship” allows him to say things he wouldn’t say in person. I expect more than one person has tossed something out online that they’d never say or do in the office or at a cocktail party.

Is there a way you could say something like “I really like this job and I like working for you, but the non-work-related conversations make me uncomfortable and/or are distracting.” Weird situation…

7

It sounds to me like he has some serious issues with boundaries. I think your concern is warranted.

8

Sounds like he’s got something other than work on his mind. Last year, though, I was working with a guy who was sending inappropriate messages to a younger woman at work, but only mildly inappropriate, and was flabbergasted when it turned out she had been saving them and finally filed a serious grievance against him. She lost her grievance because each one of the messages was only 'over-friendly" (somewhat like your boss, he wasn’t actually harassing or propositioning her, just being friendly in a way their relationship hadn’t really reached yet) and they both ended up with a sour taste, she because she felt the total ‘creepy’ thrust of his e-mails had been ignored, and he because he said if she would have given a clear message that she felt uncomfortable, he would have simply stopped. I would definitely send him a clear “Not comfortable with non-work related topics–could we stick to business? I’d appreciate your being sensitive to my needs here. Thanks” kinda message and see how that works out.

9

I think there is absolutely no doubt that he is attracted to you. I don’t know if he actually wants to cheat on his wife or if it’s just that he is the type of guy who has no mental filter and says whatever is going through his mind without realizing how extremely inappropriate it is to talk to an employee about taking a bubble bath or smoking weed together. Either way, I’d be very weirded out by it if I worked for someone like this.

You’re in a tough spot because I think if you tell him you’re not comfortable talking about this stuff with him he probably will be unhappy about that and it might impact your job. I’ve found that in many jobs, the key to success is not so much how good you are at your job as it is how much the people in power like you. For that reason, while I definitely don’t think your boss should be acting like this, I think you do have to be careful not to offend him or hurt his ego even though you would be technically correct in saying “hey, this is not appropriate and I’m uncomfortable”.

I’m not sure that this is the best way to handle it but to be honest, if it were me, I’d probably conveniently find a “new boyfriend” so that I had an excuse to turn down his romantic advances without (hopefully) hurting his ego too much but being willing to continue the chit chat about other topics like politics and music.

10

It sounds to me like he’s over-sharing a bit, but perhaps his personal boundaries are a little looser or more casual than yours. It sounds like you chat about a lot of things in your calls, not just business, so these are not single isolated statements, but part of longer conversations.

I think you can deflect some of it by letting him know that its Too Much Information. So when he starts on a topic you find uncomfortable, let him know. Message or say TMI… and change the subject back to business. He responded appropriately to you telling him not to greet you with “hi beautiful”, no reason to think he won’t take the hint with other things.

I would like to think that he is more socially inept, or overly friendly, or less filtered, than that he is blatantly trying to hit on you, but then I can be a bit dense sometimes and I prefer to look for the good in people, rather than seek evidence of malice.

11

It certainly sounds like a list of things that many Dopers would see as red flags. And welcome to the board.

12

This. There’s nothing here that screams “He wants you in a sexual way,” but this guy is definitely an over-sharer.

It also sounds he’s not dealing well with his wife’s health changes and he needs to talk about it with somebody… or anybody. And because you chat multiple times a day, he has got it in his head that you’re close enough friends to talk about it.

13

Mrs Cad had a boss like this. We joked that she was his “West Coast Wife” but it was never sexual and strangely enough was never really sexual harrassment. He just needed some companionship when he was out visiting the West Coast sites like someone to have dinner with outside of business.

That being said, that was when he was out here or little comments during business and not when he was at home so him taking time away from homelife to think about you this way is a little creepy.

14

Add me to this list. Are you able to back out of these non-work conversations, returning only to work related topics? That would work best for your employment.

15

I wouldn’t worry. Based on this statement he is obviously gay.:smiley:

“Malice” might be too string a word. It doesn’t sound like he is “hitting on you”. But as TriPolar pointed out, it does sound like he may be going through a bit of a “mid life crisis”. He probably feels comfortible enough with you to talk about this sort of stuff. The concern I would have is that he might become so “comfortible” that all of a sudden it might look like a potential romantic situation to him. So a lot of this conversation might be testing the waters, so to speak.

16

My ex wife was in a similar situation…however, being the slut that she is (and assuming, that you are not) she did more than welcome the advances.
Coworkers & others notice there was something going on (everyone, it seems, except the husband, who was off on long business trips providing for her and hers), and they brought it to managements attention. FYI a company can not only see details of the cell phones they are paying for, but they can also track the locations of the cell phones on the web. Seems these two were having many unexplainable remote meetings. One was a hospital parking lot, another a junkyard…no kidding…how romantic
Long story short, they were both fired. But not before my ex had been given a raise & position that should have gone to less attractive, more qualified, more educated, harder working, more senior staff.
So by doing nothing, you are risking your own career. You will, no doubt, get preferred treatment in your position at work, even if you do nothing. Is that fair to the other less pretty, less available (which did not matter in my case) and more qualified staff?

PS I just had a great idea. give me your Skype #…you and I starting having heavy Skype talks…you tell him that you are involved, after hours, with this guy you met on Skype. Win-Win.

PPS OK, gorgeous, now a little more about my ex…

17

There isn’t a chance in hell he’s not very attracted to you. None whatsoever. It’s classic behaviour.

Whether he’s doing this because he is actively pursuing a campaign of sleeping with you or doing it because it’s just easy to have a little pretend affair at a distance I dunno, but this stuff is supremely unethical and unprofessional.

18

It’s wildly inappropriate behavior for a nominal superior to have with someone under their jurisdiction. It’s pig ignorant stupid for him to be engaging you in these conversations.

I would worry less about the sexual angle than the overall behavioral aspect. He could be fired for putting this stuff out there, and yet that’s what he doing. His judgement sounds very, very poor which makes me wonder how he got a job overseeing others. You need to distance yourself from this guy as much as possible, if the hammer comes down he will scramble to save himself and take others down in the process.

19

I’m inclined to agree with brainstall here. He could be romantically interested in you, or he could be just way, way oversharing. Either way, you can set boundaries on your conversations. It can be pretty informal - when he brings stuff up you can say “Hey, I’m not comfortable with talking about your relationship with your wife. Let’s change the subject.”, or “Woah, TMI! So what about project XYZ…” or something of that nature. He respected your wishes about not greeting you as “Hi, beautiful”, which is a really good sign.

It’s awkward, and he’s being inappropriate and needs to stop. His motivations at the moment don’t actually change the situation.

20

Yeah, his behavior is too personal. You can approach it several ways:

  1. Blunt tactic - “You know, I’m not comfortable discussing (politics/personal fights/employees) with you. Let’s bring this conversation back to work-related topics.”

  2. Indirect approach - every time he says something that makes your spider sense tingle, don’t respond to it. If it’s on Skype or the phone, pretend to be distracted by something. “Hold on a second.” Then when you return your attention to him, redirect his attention towards work.

  3. Befriend the wife - Next time you’re in town, ask him to bring his wife along. Or send a holiday card to his home, saying “Mrs. O, I’ve heard so much about you from your husband that I feel I know you. I’d love to meet you in person next time I’m in town.” If he mentions she’s sick, send her a little note with some chicken soup. It sends him the message that you see them as a couple, and that you view her as an individual with feelings.

  4. Last resort - Pretend you have a boyfriend. Lame, but it’s probably the easiest way to let him down should he harbor any ideas about the two of you.

Good luck.