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Is this *Catch Me If You Can*? Real-life con man Frank Abagnale faked his way through a bunch of different careers including airline pilot, attorney, and medical doctor (using dialogue from medical TV shows like *Marcus Welby, M.D.*).
Good guess, but I've seen that one and I know it's not that. It was a comedy, if that helps.
I saw a clip of this film on You Tube. A man (looked a bit like Ryan Reynolds) is in a hospital, and he's in disguise as a gynecologist. He's not doing it so he can look at lady parts, but because he's in hiding or on the run or something. But sure enough, a pretty young lady comes in for a checkup, and he has to bluff his way through it.