A
female
age
36-40,
*eminik
writes:He everyone I could really use some sound, constructive and useful advice, I would be much obliged. I work with this guy who is one of my supervisors, I like him a lot and he befriended me on FB. Anyway my question is I need to approach this situation delicately, so how exactly would I go about, and keeping it out of the work environment asking him if he would casually like to go out for a cup of coffee, I am interested in getting to know him better. I can't foresee asking him at work because that would draw unwanted attention. Would it be tacky of me to send him a message, if so what should I say and how can I prove to him I am willing to keep things private.
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female
reader, RedAthena +, writes (17 August 2011):
 It is a really horrible idea to date a supervisior.
It is incredibly unprofessional and he could be blamed for favoritism if you get ANY sort of special treatment.
You could get an awesome review based on hard work, and suspicious coworkers will think it is because you are involved with him.
My advice-if the person is really worth pursuing, change supervisiors first.
Trust me, the TRUTH does come out. People are not dumb.
A
male
reader, anonymous, writes (17 August 2011): My advice on this, unfortunately, is that you should not pursue a relationship. I know you stated you like this guy a lot, but he's your supervisor. Dating in the workplace is tricky enough when two people don't work closely together.... and when one reports to the other, the risk is just too great.
To be completely honest, even being friends on Facebook with a supervisor is not a good idea. I certainly wouldn't do it. A line has to be drawn between your career and your personal life, and when it gets blurred drama has a way of cropping up, sometimes to the point of personal disaster.
Really and truly, you should look elsewhere for potential romantic partners. Just keep it professional with your supervisor.
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A
female
reader, anonymous, writes (17 August 2011): Well as you say hes your superviser so you must tread carefully,
number one; as sometimes work and relationships dont mix to well, coz if it doesnt work out you may /will both end up feeling very uncomfortable around eachother (so bare this in mind)
but also number two; becareful about what you put on face book as its not always a good place to open up to much if you want to keep it a sercet.
What i would do if yor genuingly interested in him,
is when you are both alone at some stage at work be a little flirtatious to start with (otherwise you'l never know if hes interested as well and therefor you may be setting yourself up for a fall)
just gently though nothing heavy just compliement him like "is that a new cologne its really nice...." or something like that.
Then do this probably twice on that day, then wait and on a completley different day (either then ask him out on a private messege on face book ) or 'preferably' when your alone again ask him if he wants to grab a coffee at this place youve been dying to try, yeah it may sound cornie but at the end of the day if hes interested he'l just be flattered your the one asking as many women dont do the approching.
Gook luck ;-)
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A
male
reader, Daniel the love doctor +, writes (17 August 2011):
 Well generally I wouldn't recommend asking someone at work out. Because if it doesn't work out, you may feel awkward working around/for them. But if you must, and you'll probably do it anyway, then you may want to give it more time. Build up a friendship with him first. Talk to him more at work, on FaceBook, etc. And if things go well and you find a common interest, say "hey I like what you said about...(whatever), or I know you enjoy..(whatever)...as do I. Do you want to give me a call tonight...(or ask) go for a cup of coffee...so we could talk little more about it?"
If he says that he can't because he has a girlfriend or he wouldn't feel right calling you/seeing you out of work hours, then you have your answer. And just tell him that it just would've been a talk in a friendship way, but you respect his wishes. If he says yes, then that could be the gateway to talking to him.
Hope this helps!
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