Ok so here's the deal- I'm a PGY-2 resident at a smaller community IM program (16-18 categoricals per year). I started off cycle by 3 months so I've become much closer to the current PGY1 class than mine as a result. There's only 5 categorical girl interns and I've become pretty close with one of them (we have never been on the same rotation and most of our rotations have been in different hospitals so we mainly see each other in social settings every 2 weeks). In the beginning I was pretty aggressive initiating/flirting/etc making it pretty obvious I was into her (atleast from my point of view) without ever asking her out in person. Since then I've backed off and have been ok with becoming better friends (texting regularly, a couple deep conversations) but I'm still into her. I was originally going to wait until her intern year was over (she has a brutal schedule the next few months) when she is less busy to let her know in person that I want to date her just so I can know for sure where I stand instead of always wondering. However, I am going to be her senior resident for a few days when we overlap rotations next weekend- should I just talk to her at the end of her last day before she goes on vacation to let her know how I feel or is that a bad idea?