Over the course of a long, single life, many men get very skilled at the "process and execution" of an evening out with a woman. They've got their favorite bar to start the night, a couple of restaurants that are just cool enough, and a handful of later night watering holes when the night goes as planned. They have learned where dozens of women grew up, where they went to school, what type of travel they like and what kind of dog they want.
But these men are still single.
These men have confused the event-planning portion of meeting a woman with the real purpose of spending time with someone new -- to figure out if this person is "The One". When your buddies ask "how was your date", the answer that runs through your head shouldn't begin with "we had a great meal at..." (although that's what you can tell your friends) it should begin with "I found out that we share/don't share some of my core values like...". So what does this mean for you men? It means you should no longer be judging the success of your "date" by how good the meal was, how hot your date was (OK, you can include that a little) or how much action you got, but rather by how strong an assessment you made of how your values are lining up. What that means is that you have to go into the evening with a few values you want to probe for -- adventure, worldliness, philanthropy, compassion -- and despite your urge to tell some of your funniest stories from college or talk about work, you need to orient your conversation around surfacing the values you hope to share with someone you will be with for a long, long time.
Being great at "dating", or planning out fun nights and leading a joint background review with some new woman is a fine skill, but don't confuse this with what you really need in order to be successful in finding "The One".