A co-worker friend of mine (we'll call her Ms. T) told me yesterday that I "should go out" with another co-worker (we'll call her Ms. Y). Ms. Y also happens to be one of the Assistants Directors. SO then I asked Ms. T "why? did you hear something?" I got very curious as to why she mentioned this and so she said "I think you two would make a good match." And that she had just thought of it. Now I've never thought about Ms. Y like that before but now that Ms. T has put the seed in my head, i am thinkin about it now. And the weird thing is that a couple of months back, SOMEONE else said the same thing to me about Ms. Y (after she broke up with her long time BF) so now I am definately wondering whats going on.... I'm kind of sure Ms. Y is single ... And after Ms. T mentioned it to me, I started checking out Ms. Y really strongly. She doesn't have the greatest face, an alright bod and she's also very nice. But the thing here is that ... she is basically one half of my bosses. We have two assistants directors and one head director. She is basically in 3rd rankin of order. I think it would be weird to date a co-worker who works closely with you (i've asked about this before here) much less someone who is above you in job position. I don't know how that would be....It would be weird. If she wasn't an assistant director, i don't think it would be weird but she is. I wouldn't even know how to go about this....Because me and her are not even "friendly-friendly" like that. I mean we say hi and goodbye and the usual small talk but not anything in-depth and nothing to show interest on either side. I tried thinkin about a way of putting it out their.....and seeing what happens. Only cause its a bunch of women that work here and you know women....a juicy bit like this and it will spread quickly...and eventually back to Ms. Y's ears. And MAYBE she'll start thinkin like I'm thinking...hahaha... I don't know.....Any advice on this? btw, I do realize I could prolly just ASK her to go out for some drinks or dinner one night but again......this is basically like one of my bosses. I definately don't want to put that out their and get rejected cause of that.