Does dating get easier after the first?

I started dating my first girlfriend when I was 19 and she was 18. She had dated a few guys before me. We were together for 5 years, but broke up a few days ago. In high school I was a bit awkward. I guess you could say I "bloomed" in college - started working out, had a nice body, was very involved with friends and family, etc. Most importantly, I became really confident in talking to the girls around me.
My issue wasn't being unable to keep a girl interested. Instead, it was not knowing whether she was interested, and not really knowing how to ask her out.
Now, I'm 24 and out of college. Haven't had much luck meeting women since I spend most of my time studying. I'll be starting Grad school in the Fall of 2017.

So, does it get easier to date after your first relationship?
For those of you who sought higher education (medical, law, grad, etc. school) would you recommend trying to date before starting? Or, just wait?
Does dating get easier after the first?
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