How to have good sex on the first date. I once had a great first date playing bocce in a park. Otherwise, use your imagination. Don't forget that men often have burdens to bear with first intercourse, and many feel pretty serious pressure to do it "right" and make it good for everyone. Or, if she's of a more intellectual persuasion, perhaps offering her a copy of your favorite book might stack the odds in your favor. As well, if pain during intercourse continues and helps like these don't fix things, check in with your doctor: I once had a great first date playing bocce in a park. It is entirely likely you'll feel a lot of different things, just as you often do with other types of sex. Bookstores Coffee shops School alumni events Trains and airplanes The street Her first anal creampie.