how can I get my boss to ask me out, we are both frusterated, but I think he's nervous/shy? help?

Question

recently one of my co-workers told my boss I liked him, he was ALL SMILES and the next day I worked with him, he was weird, like always around me, kept looking to see who I was looking at, the next day I confronted him and told him I knew he knew, he said he was ok with it and that my hours weren't cut but that I was getting more, this guy is very confusing and hard to read, I feel he likes me back , but hasn't made a move?? how long should I wait or should I do it first? My birthday is 1 week away and I wanted to spend it with him....HELP......

I have dated one of my opast bosses for 3 years, he was the store mgr and I was his asst. work was GREAT... There is no law saying we cannot date, we don't work together everyday and he only wants me to work with him, he and I both have discussed that we have other jobs to fall back on, I just feel if you don't go with your feelings you may make it worse at work, with the tension and frustration that builds, we are very mature about it and we are both grown adults(30ish) , it takes maturity to handle a work relationship????

Answer 1

No, no, no, no, no!!!! Never, ever date the boss. What happens if the two of you date and then it doesn't work out? Will you enjoy being fired or, if he's afraid of a sexual harassment suit, will you enjoy being stuck working there after it's over?

Look for another job and, once you're in that other job, sure, then ask your ex-boss out. Even if you don't break up, any raise or promotion you get will be assumed to be because he's banging you. As for that big mouth co-worker that told the boss that you like him, both you and the co-worker need to GROW UP.

Answer 2

Just stop right there. Don't move any further. He knows you have feelings for him now so don't push it. He may not have the same feelings back and if he does he probably doesn't want to make the work environment strange or awkward. This is a tough situation, there are rules to this and the boss dating an employee opens the flood gates to a whole lot of grab a s s at work. You just need to take it slow and let him follow through with initiating the relationship. If he doesn't don't jeopardize your job by pushing the subject. Good luck.

Answer 3

Well if he already knows and he has not made a move, perhaps he is afraid to mix work and pleasure and he sees it as unethical. or maybe he is simply shy. Either way if you really want this you must analyze the consequences and what you are risking here. Do you care about jeopardizing your job? If you don't... I say go for it, make the 1st move! Just casually mention how your birthday is coming up, and well you are going to party and it would be great if he was there with you. Don't look desperate, but show some enthusiasm.... remember guys love when girls are not all over them all the time, they like what they are not sure that they can have!! GOOD LUCK!

Answer 4

Sigh. Are you prepared to go work somewhere else? It's a very very bad idea to date your boss. It leads to so many problems.

If you want to go out with him, ask him out. But if it turns into a real relationship, you need to get a job somewhere else. And if it fails as a relationship, you're going to be in a bad position.

Furthermore, most companies disallow a boss to date an employee because it leads to sexual harrassment lawsuits. So he might say "no" because it's against company policy. You need to respect that, because do you want to be with someone who breaks the rules? That doesn't bode well for your relationship.

Answer 5

ur story sounds pretty cute, almost like taken out of a movie. but ill tell u bout reality. the worst thing u can do is hook up with somebody from work especially ur boss. relationships like that usually never work, cuz u see that person every day and u also gotta interact with other people and that usually get the other person jealous. plus if hes ur boss and things dont work out, hes probably gonna make ur life miserable and maybe ur even gonna have to quit ur job. im just telling u all this from experience, it usually never works @ the job.

Answer 6

Relationships with coworkers can be very tricky. Few relationships last forever, so consider how will it feel when you have to work alongside your ex. Also consider, how it feel to work alongside your boyfriend. Everyone needs some personal time. The fact that he is your boss magnifies all of these problems a lot.
I wouldn't recommend pursuing this, especially since he's not.

Answer 7

Usually bosses can get in lot's of trouble having relationships with their workers so this could be why he isn't doing anything about this. When you are off the job site, maybe you should then talk to him about how you feel.

He may value his job more than any relationship with a co-worker.

Answer 8

LoL, obviously he's more stuck on the "no dating co-workers" rule. Plus, dating you can ruin his authority with the other employees. Things will get weird at the workplace.
Maybe, if you are not in love with your job, you should quit it and then ask him out. I don't think he'll agree to going out with you if you are working for him.

Answer 9

Maybe you should wait for him to make the first move because if you go first and he rejects you things could get a bit uncomfortable at work or if you get together and it doesn't work out it might get ugly so watch him closely and see what he wants before you make any decisions. It might bite you in the ***

Answer 10

Your coworker told him you liked him and you CONFRONTED him by claiming you knew he knew you liked him? Ok. so? Maybe he needs his job more than he needs a date with you. Some companies prohibit the boss from dating subordinates.