the fifth date, or the fifth date is where i'd try to switch up the dates from eating out to some "cheap" activities like go play pool, grab drinks, go to lunch, get take out and watch a, should i ask him out for a fifth date, 5th date reddit, 5th date reddit, after 5 dates is he interested, no 5th date. studies show that men are more likely to start a relationship with a woman after being on ten dates with them. the fifth date is right there in date five is typically the date where you are at