I have a crush on my boss and he keeps flirting with me too!!!

Question

I work with this guy that is like 20 years older than me and he is my boss. Normally I work with him and maybe 2 other people during the day. I always get a weird feeling in my stomach when I see him and he always comes in with a smile and sweet hi. During the day there are little fun comments and it looks like innocent flirting. When we all go out for a fun night we end up having too many drinks and the flirting picks up on both ends and with other co-workers. One time we ended up hanging out at his house after work like a few weeks ago and we got a tour of his house and when I saw where he slept I could only picture sleeping with him in that bed. It got really crazy that the comments made had me making sure not to be alone with him in the same room. He apparently has dated younger than his age and he is a nice guy but I don't think he will step over that line. But apparently they are having a Halloween party and I am concerned that something may happen. Should I be concerned?

countygirl · Accepted Answer

He is your boss, so I would say donlt do it. Dating in the work place is a very bad idea. Many companies have policies againist it and with good reason. Beyond the fact that you could both get fired over it, there are other factor to consider.

Your co-worked may loose respect for you if they think you "Doing the boss".

Then you have to think how it would effect your working relationship with him. It can be hard to separate "personal" & "work" stuff. Not to mention if you two would ever break up. Think how awkward it would be not only to see and work with your ex every day, but have to take orders from him. What if it ended badly? Think of how uncomfortable that would be.

If you are really set on this guy. I would say think about transferring departments before doing anything.

As far as the Halloween party. Think hard before even going. If you do go - don't drink (NONE). You need to keep your self control and keep your distance.

As for right now, stop the flurting. It will only get you into trouble and start the office to talking ( I haven't seen an office setting yet that doesn't have a gossip hotline lurking behind closed office doors & around the water cooler).

You career could depend upon the desisions you make right now, even follow you to other jobs in the future.

Choose wisely and best of luck.

Beastieboys95 · Accepted Answer

I think you should stop whatever you two are doing. Because he is your boss and things can turn really bad and awkward if you slept with him or started dating him and you two broke things off you can loose your job. Or have your coworkers think of you wrong because your doing the boss.

flower1000 · Accepted Answer

lol  no your a big girl now I always liked older men  go for it but make sure you don't get sacked after it so if your going to do it do it right lol or don't do it keep him hanging  men love that it drives them crazy lol

kriskiss · Accepted Answer

I don't understand why you have the tone that you don't want something to happen-when in reality the real undertone is that you do want something to happen.  Like you said when you saw his bedroom and you could only imagine sleeping with him in that bed(so you really do).  However you go on to say you want to make sure not to be alone with h I'm in the same room--why not you want something to happen as you said you imagine sleeping with him in his bed--so your contradicting yourself you make no sense at all.  Then you go on to justify that you want him to bang you because you say its only an extra job meaning its worth losing if it means being with the guy--get a hold of yourself and your emotions and figure out what you want.  you seem like you want to do the guy, but then say you don't want to put yourself in a position where that can happen which makes no sense---u may be bipolar or crazy

jimi_s · Accepted Answer

just be very careful if things go south you may have to look for another job...

Anonymous · Answer

Tone the flirting way down starting right now if you don't want anything to happen at this Halloween party and don't get drunk while you're at the party so you still have your common sense.