Havent been in the dating scene for over 16 years. Depends on what you did on the first date. Did you just go out to eat dinner? Movies? I would say on the second date...make it a fun date. Dont get romantic just yet, but make it sweet and unforgetable. When i took my wife of 16 years out on her first date we went out to a nice dinner and then to the movies. The second date, we went to a drive up restaurant that had outside seating, went and played putt putt golf, drove the go carts and met a few of my friends at a local bar for a few drinks. She had alot of fun, obviously because about a year later she accepted my proposal.