Flirting with a coworker

Do nothing! The worst thing you can do is mix work, and romance—really should keep them separate. I’ve witnessed the dramatic fall out form workmances, in my early years, and said “screw that.” For that very reason I instituted a “no dating work policy” and have stuck to it for over 35 years—it has worked very well for me :o)

Its highly possible he has instituted those workplace boundaries as well, which one should when in a ‘management position.’ He knows how bad it would looks, dating a junior co-worker, so most likely won’t go there with you, which is why he’s treating you no differently than he does with his other co-workers, as he should.

I would not push it, or do anything. I wouldn’t go past your work relationship boundaries with him. If you push this, and he’s not interested, you could lose your job over it. If I were you, I wouldn’t pursue this ‘crush’ you have with him, and only date outside your workplace.

Thanks for your responses. I appreciate that.
However I don’t think he is seeing me as a booty call. When we are together he always asks a lot about my interest and remember things I have told him before.
It’s a student job so it’s not like my whole career is in stake :)
Last time we talked about tennis.
I was thinking about maybe asking him this Sunday if he wants to play? I am a member of a local club and they have open court access on sundays :)

Your supervisor text you at midnight?!

Men will see how far they can push things before you say no. You accepted midnight calls and went to a late drunken party. I do not accept calls or text after 9:00. It goes to voicemail. Men are supposed to initiate dates….if you initiate you will not know if he likes you enough to ask you out (drunken parties do not count). Men want to respect women – show him you are worthy of respect. He may not want to date someone from work – so do not ask him out. But dating someone from work is very tricky when you or they stop dating. Trust me.

LOL I was going to say the same as Lane. Since you’re young and this isn’t a job that could hurt your career, go ahead and chase him and sleep with him and see where it gets you. I had an office romance ONCE and it was fun while it lasted and then it really sucked when we fizzled out. I would never do it again. But it sounds like you need to learn by having the experience in a situation, where luckily the stakes are low.

Here are some takeaways for later once you’re willing to open your eyes and see how men and the dating game work:

1) Your boss at any job should never being doing things like this. It’s highly inappropriate to fraternize with a subordinate. He is presumably older than you and old enough to know better. He’s not very smart.

2) The late texting inviting you over to drink is a red flag coming from any man. He’s testing to see what you’ll let him get away with. You’re failing the test by responding and then going over there. It shows him you have low boundaries and he can say jump and you’ll say how high.

3) Don’t chase men. That means you don’t directly ask him out until he’s shown you he’s for real. That may sound hopelessly old fashioned but there’s a delicate balance in courtship and it’s the man’s job to pursue you. That’s how you know he’s genuinely interested. Let him work for you – a guy who is really interested will want to prove himself to you and make you happy.