I hadn't had trouble dating girls until i started med school last fall....
Honestly dude, it's not worth it. STUDY for STEP 1, it's the most important thing you can do. Women will always be there, but your future may or may not be there depending how you do on that test. The worse mistake you will ever make in life is letting the potential of females dictate your life decisions. Never let a girl influence your actions (unless she is already your wife) or you will get burned. With that said, here's my take on dating in med school:
Peak level free time and hence time to play the field is def M1. It goes down hill M2 and is non existent pretty much M3 and into the beginning of M4. There is about a 6-8 month window M4 where you have ample time.
Bumble/Tinder: hit or miss. The good looking women get right swiped by EVERYONE. I live in a large city (with tons of single women) and even then it is mostly the average and below average women who are actively using the app to find a date. Most of the hot sorority girls who are 8+ just use this app for validation (or seldom try to match with a guy who looks like he is taking pictures for a GQ shoot). So while this may seem like the easy way out, it remains a difficult option unless you are insanely good looking, have puppy pics, and tall. Or if you have average to low standards.
Bars/Clubs: Also seems like the go to option for most guys. You have at most one night per week when you "think" you can go out and pick up women and then recuperate to finish the weekend strong with studying. Especially when you just start your clerkship or module. Again, it's difficult. From my experience, women don't go to bars to necessarily hook up with anyone. Notice that the extremely good looking girls are either in groups of extremely good looking girls or with some dude already. It's rare and I have done it, but it takes work and very strong wing men to pick up women at popular bars. Remember these girls are just out to have fun and gain attention, they could care less that you will be a plastic surgeon some day. They just want to get hit on by the hottest guy in the bar. Conversation doesn't go a long way when the music is extremely loud, so again appearance (just like on apps) is all that matters. Most dudes in med school are average at best, so again you're likely screwed.
Med school class: the hotties are always scooped up in undergrad by either a) some frat dude who seemed cool back in the day b) business guys with rich parents who already make 6 figures c) some dude at the right place at the right time back in college. People aren't single at the age of 25+ without some reason (like myself, I have no self esteem due to being average height and have a sub-average Step 1 score coupled with the PTSD or an average MCAT score). The rest of the people are nice friends but again there is a reason they are still single.
Social events: your best chance again is M1. Particularly M1/M2 summer. Join intramural sports, take cooking classes, yoga classes, march for women's rights, etc. where there are hoards of women. You actually have free time and can talk to women about mutual interests. Day game goes a LOT further than game at a bar or club. In my experience this is your best chance to actually get to know the girl and get something out of it.
Friends of friends work too. However, unless you go to med school in the same city as your undergrad or have a lot friends move to the area...not going to work. Girls in med school are not the best at sharing their friends....let's just put it that way.
When all else fails, flirt with the nurses.
AGAIN, FOCUS ON STEP 1 and DON'T EVER MAKE ANY DECISIONS IN LIFE THAT REVOLVE AROUND A FEMALE. NEVER, NEVER, NEVER, NEVER, NEVER LET A FEMALE DRIVE YOUR DECISION MAKING, IT WILL NEVER END WELL.