Am I infatuated here, what should I do, is it wrong to ask her out?

There are a hundred reasons not to date your supervisor. Regardless of how you and she may feel, if she is smart she will not get involved with you while she is your superior. This is practical advice. Too bad feelings aren’t always practical.

Do NOT, I repeat DO NOT ask your supervisor out. Bad idea.

Go for it. Following convention leads to conventional results. Go for something unconventional and potentially far more exciting.

Ah yes you probably right, such things can only end bad right….

I’m guessing from your comment…. “she must be in her 30s maybe 40s”, that your a young bloke. & as such you have a duty to all men to ask her out & see what happens.

If she hasn’t shown any indication that she is interested in you, then I wouldn’t ask her out.
If you did ask her out, and she refused, you would be in a very uncomfortable position, as she is your supervisor.
Take things slowly and see if she starts to respond to you, then ask her out.

I agree with @loser. Back away slowly from the boss. Sounds like you have a work supervisor that you get along with well and makes your job enjoyable. Leave it at that.
In this economy its hard to find a new job, especially hard to find a boss you like and who likes you. Its easy to go fishing in the nearest pond, but if things don’t work out you may end up holding a dead fish. Go sea fishing instead. You can always throw them back in the ocean.

Ask yourself if the job you have is important to you and if the answer is yes…keep a minimum distance between you and her. If 10 years from now you are going to be saying “dang I should have test driven that hottie” then go for your test drive young man. Life is too short to not grab the brass ring in front of you if and when you can.

I agree with @Cruiser. If your job is really important to you, if you are building a career at this place, then dont make a move while you are there. You can always hit her up once you leave if you still feel the same why.

Remember, as much as you might think its not, it could be the fact that she is your supervisor that is getting you a little hot. And once you leave that work environment, she might not be that appealing.

If you don’t mind if you are working there or not, or it is just a job to get by, i think you should definitely ask her out…..go on, bang your boss :)

I think do it. You only live once right?

Though I agree, if losing your job will put you in a world of hurt… wait it out a bit.

Also, depending on your company, there may be a way to switch areas if things get serious or go badly.

I’ve had some time to think more about your question. Next time you guys are at lunch and casually (without being too obvious) mention that you can’t believe someone so attractive and smart hasn’t been offered a proposal of marriage. She may come out and say she’s never been married, or has been and is divorced or is currently with someone but she doesn’t believe in commitment, or that she doesn’t believe in any kind of long term relationship, or she’s gay, or she is solely career minded and has no interest in any kind of relationship.
This way you will know what your chances are. If she is gay, or doesn’t believe in anykind of a relationship or has several divorces under her belt. You will kind of know where you stand. Especially if she does sense this is kind of a personal interest inquiry from you than she will make it clear you either have a chance or no chance.

@JeffVader LOL! I actaully lauged out loud after reading your answer =D Omg..
@Pandora That sounds familiar, guys have tried that line out on me in the past. =P

@whyigottajoin Hehe, just returning the favour from yesterday :)

Depends. Do you need this job? Asking your supervisor out can backfire and it can possibly be against company rules.

If you don’t need the job, then go for it. If you do however, admire from a distance.

Go for it. But if it does not turn out, or work out.

It will be at the least a weird situation, or will eventually lead to the demise of your job.

As the saying goes, “don’t shit where you eat.”

You seem to have a good friendly relationship with your supervisor. Best to leave it at that. Any relationship would be disruptive to the workplace, either directly or by causing gossip among other employees. I admit that I am rather conservative in such things, being from a military background where such relationships are forbidden, but I can see why they are.

I am in a similar situation. One of my employees (36 years younger than I) had only made a remark to a co-worker that she found me “interesting”; this sparked off a storm of rumors that scared the hell out of me, even though niether of us had made any move toward a relationship. I had to physically separate our work areas to make the gossip stop.

Relationships with 10–20 year age differences are possible (my late wife was 20 years younger than I), but tend to be the exception rather than the rule. If you moved on to a different employer, or even another department, it might be worth a try if you find her sufficiently interesting. As long as you are “vertically linked” in the same chain of command, I strongly advise against this.

Hey! Michael Scott did it!

But seriously, stranger things have happened. If she says no, I guess that could get pretty awkward. I like @DarkScribe ‘s answer though.

@whyigottajoin LOL, Replace, Pretty and smart with Handsome and Smart and you can use it on guys as well. I’ve used it on males and females. Not so as to hit on someone but to find out how big of a jerk am I working for. If you ask a guy you can find out if he hates women by his answer. If you a woman you can find out how she about relationships. Often people let their feelings leak into the work place and how they treat you.

Well, its not hard to understand that you have fallen for this lady. you did not mention your age as compared to hers. it really makes no difference as long as you both are happy. you are in a peculiar situation. she is your supervisor and that can be good or bad. you never mentioned any comebacks from her. i would first determine if she is married. if so, forget about it and look elsewhere. if not, its time to turn up the heat. ask outright, if she is married. this will resolve one problem upfront. if single, go very slooooow. you are with her each day and that would be uncomfortable for me. but, maybe not for you. sit down and write her a simple note, like an invitation and keep it short and to the point. she seems to like this. ask her if meeting her for coffee after work would be appropriate. after all, you two are not strangers. if she accepts, then again take it slooooow. this will be a great time to discover what each of you really have in common and its away from work. like the saying goes “nothing ventured, nothing gained”. if all works well at your coffee date, then i believe you can take it from there. john

I hope that you didn’t develop too much interest.
You can ask out whomever you please. Do it discreetly, especially considering that she’s your supervisor, she’ll want it to be under the radar.
So go for a friendly lunch or coffee so you can present all attractive traits you have. Then eventually, make plans for a dinner date. Remember to plant the seed first.

If you did ask her out, you put her in a tough situation. Anti-harassment rules make it very difficult for superiors to get involved romantically with subordinates. It puts the company at risk of a sexual harassment claim.

If she tells you no, and tries to use the sexual harassment thing as an excuse, you’ll still think she likes you even if she doesn’t. If she tells you no and makes it clear, then you will have spoiled your work relationship.

But maybe she is a little bit of a risk taker, and maybe you don’t really care about how things are at your job. Maybe then, if you ask, you could have a great affair. Maybe even more. I wouldn’t put money on it, though.

What is the company policy? HR generally takes a dim view of vertical fraternization. Sometimes even lateral is prohibited.

Yeah, true. When I worked at Chick Fil A and started dating a coworker it was a huge issue even there. The managers were serious dicks about it even though it didn’t interfere with our work at all. They went out of their way to make sure we didn’t work ANYWHERe near each other and sometimes would make sure our schedules were opposite. It was really stupid, because half the people that worked there made up my group of best friends at the time so really it didn’t matter if it was my boyfriend I was beside or a best friend. It was really silly. And it was only Chick Fil A!

Looking for love at work is like lighting a match in a sea of gasoline.

At best if things go well there will be much gossip, rumors of favortism and more. Any praise, promotions, sought after hours / assignments will automatically be suspect to your co workers regardless of wether it’s true or not.

If things end poorly she can make your life at work very unpleasant. At best things would be akward.

Still if your mind is made up be honest with her from the start about your expectations. If your looking for something light and casual let her know.

With both of you having the right expectations and being on the same page from the start there are less chances for animosity if things end poorly.

Before I married I dated more than a dozen employees of the various organisations that I worked for. Dating someone with seniority is no problem, dating someone who actually works directly for you in a subordinate role can be possibly problematic. Companies do not have a legally enforceable right to prohibit dating between employees, only the Military even attempt to go down that path. Anti harassment rules do not prohibit asking someone out, only refusing to take no for an answer.

Thanks for the answers.

I decided to man up and just ask. So I brought up a conversation and tried to cleverly insert a question without being rude/strange way of asking her if she was single.

When I had asked it was rather obvious the gesture as to what I was getting at, she told she me she flattered but sorry could not date someone of that age. Not directly at me but just in general.

And she was taken sigh but that is ok least I know where I stand now haha.

I did though from this talk find out more about her she told me she was married, then became a single parent and only recently found a good man as she put it.

I won’t flirt anymore with her or the like but hopefully least be friends. I have nothing but respect for this woman.

Hey good for you for doing it!

@Steve_A Good for you! You got the information you needed and preserved a good working relationship. A good sign of maturity, my friend.