Couple anecdotes I'd like to share, given I've had too many experiences in the subject matter .. (No, I'm not bragging)
If you're going to try to get with this guy, you need to gauge his level of involvement/how much he would want out of this. Some guys aren't willing/wanting to commit to anything and just want the physical aspect of a relationship. Also realize that there are girls like this, too. If you can't handle that, then don't lie/pretend like you're going to sway him/her differently. You can usually tell by asking simple questions while you're having coffee/talking. I wouldn't mention it in the first interaction with the guy/girl, but after a couple times. So, remember what I just said - you have to feel/figure out what they want. I, personally, have my apprehensions about dating while in school. I have had to personally deal with the frustration of telling a girl it's over after taking chances while in school and seeing my grades drop. Some people can't do it, some can. So, if the other person only wants something physical, don't label them as selfish/douchebags. It's normal and honestly commendable to be honest about it.
Second - if you really want to not be obvious about it, have a get together. People don't study all the time in med school (just 99%) and want to unwind. This doesn't always involve getting blackout drunk and dancing at clubs. Some people enjoy just having a couple drinks at a quiet place and eating/talking. Doing it groups makes it less awkward about bringing up things like relations/etc. When you're in a group of familiar people, you're less stressed about talking about things because other people can relate. So, you get to see what this guy likes/doesn't like and what he wants.
Here's how I PERSONALLY handled the beginning of second year - My roommate and I threw a massive get together/party for ourselves and the MS1 class at our place. We literally told them the truth - you are NOT going to have a chance like this to interact together/relax/have fun like you are right now. Come, drop by, have a drink and get to know us/each other. It was probably the best experience ever because everyone got to know each other. The unfortunate thing is that our school is divided by campus sites and we only have 20 people per class 1st/2nd year. But the point I'm making is this - having a little get together at someones place and inviting others is a great way to get to know each other. You're all together and in for the same thing.
Lastly, don't feel bad about your situation. If there's one thing you don't want to do is let this get the better of you. Rejection will happen, a lot. But it's not yourself at all. You're young with a goal. Conquer that goal without letting things like relationships/pursuing relationships get to you. Be calm. Take it from someone who's in the worst place in med school (2nd semester/boards) - you DO NOT want this to take a toll on your performance. NO ONE will understand what you're going through outside of med school. It's a tiring/stressful/frustrating experience. If a guy is backed off at a bar because of what you do, then don't tell them you're a med student. Tell them you're a student. Don't focus on your education...that's not what you should be talking about. Honestly? When I talk to a girl at a bar/get together and she asks what I do, I usually just jokingly tell them "I'm unemployed" and see her reaction. Then I laugh and calmly tell her I'm joking/I'm a student. This does two things - 1) establishes that you have a sense of humor/can converse and 2) you are doing something with your life.
