I have the biggest crush on my old boss...

Hi everyone,

I have a dilemma at work. There is a guy who I work with who I have a HUGE crush on. He was my boss from January-April so I worked a lot with him, and we always teased each other and had a really good relationship. However, last week I transferred departments, so he is no longer my boss. To celebrate my transfer, my work friends and I went out for drinks and I invited him, which he accepted. So I had a few drinks with him and asked him for a ride home (he lives close) which he gave me. I have had a crush on him since I started working with him but now I am finally not his subordinate so I feel like it wouldn't be a problem if we saw each other. I only see him a couple times a week. But he hasn't made any moves so I am not sure if he is interested. Would it be weird or awkward if I just asked him out for drinks? He hasn't really sent any strong signals, but I'm not sure if he's just being professional since he's a manager. Help please!!!

It might make things very awkward, especially if he isn't interested.

I don't think work is the right place to meet a mate. It's distracting and it can make things complicated if it doesn't work out.

My advice would be to not make complications where you need a paycheck. It makes more sense to not mix business with pleasure.

Some companies frown on employees dating each other. Do you know if your company is that way?

Are you sure he doesnt have a girlfriend or wife?

Yes, our company is fine with it as long as it is not your superior.

Also, I am positive he is single. I have also found him on a dating app, so I know he is looking!

I would not make a move. There could be a time where he WILL be your boss again - will be heading up another project you get grouped under. I would just stay in touch in a professional relationship. If he is actively looking, then he would have made a mood or would do it soon -- just because you have a crush doesn't mean he feels the same way about you - and that's nothing on you. He could be dating someone - even if not officially a girlfriend. Just give him the green light if the opportunity arises - a very general one "oh, I have been meaning to try that" = or something innocuous.

Should I at least add him on Facebook? Or is that too obvious that I like him?

Should I at least add him on Facebook? Or is that too obvious that I like him?

Add him on LinkedIn. Do not add on him on Facebook. I would not add him - you will be upset if he is dating someone and will be upset if he doesn't understand that adding him on Facebook means you 'like like" him.

He already added me on Linkedin about a week after working together at about 2am. But I will not add him on FB because he might read too much into it.

He already added me on Linkedin about a week after working together at about 2am. But I will not add him on FB because he might read too much into it.

I would leave it be. Don't worry about "reading too much into it". I recommed trying to meet other guys for coffee dates -- because the crush may break a little and you will know whether the crush is just because of work proxmity and no other prospects and you think "what was i thinking?" before you embarrass yourself, or your crush will turn into interest that is more realistic - no teenager feelings -- but more "if he asks me out, great, if not, thats fine, too"

What's the problem with Facebook? It's not like its a dating app. It's a social media site where friends and family can interact.

Several things to string together - he may not be a supervisor in your department, but he is still a supervisor and should be planning for future promotions whether with your company or elsewhere. Especially in these times, he would be a complete moron to dabble with the staff and risk a career stunting harassment complaint.

You were out for drinks and even a drive home. Nothing happened at all that night or afterwards. So not only is he not a complete moron, he also isn't socially interested in you at all. He will remain as coworker status.

Harmless work crushes are fun to enjoy to break up the monotony of the day as long as you do your job and know that nothing will develop from it. Fb is also harmless to add, I have several coworkers as "friends" on mine, female and male, and it means nothing more than that. But in your case, it is not a good idea to add him because it will very likely add to your overthinking about him, building of your one-sided feelings even if you find he has a relationship, and distract you from meeting someone who will be interested in you as much as you are in them.

My advice about not dating someone at work obviously went right out the window.

It's still good advice though, you don't mix social with work, it's a bad idea.

But I also agree with what someone else said, if he was interested (being as he's looking) he would have made a move by now.

Perhaps he doesn't want to mix dating and work.

Keep in mind that even if you just see him twice a week, if you do get together and it does not work out, those two times a week will be hell.

But if you want to date him anyway - I guess you'll just have to see if he asks for your number and asks for a date. You could make a move, sure, but you risk rejection, which is painful. besides, most guys will do it anyway.

Other than him being your ex-boss or someone you know, what else is up with him? Do you know anything else? Does he have kids? How long has he been in the country? When did his last relationship end? What kind of work ethic does he have? What are his goals or anything in general? Anything??

If you worked with him, surely you know a bit more. I wouldn't embark on anything without having a good idea what someone's about. You have a lot at stake and it also depends how much you value your career or your resume past this employer(if this ends badly, how would it affect your future?).