If you're not having fun on a date, you know it's not meant to be. But what's worse is when you don't laugh out loud at any point during a date. If you want to make your love interest laugh, you can't be uptight. The general rule of a good date is to loosen up. Tell some jokes and goof around. Just remember to not try too hard or you might look desperate.
Overanxious chivalry
This tip is for guys. Before the date, go to a thrift store and buy a cheap coat or jacket. For part of the date, go on a walk. When you come to a puddle or muddy spot, throw the cheap jacket down onto it. She'll find your attempt at chivalry cute and charming.
For ladies, reverse the gender roles throughout the date. Pull out his chair at dinner, bring him flowers, open doors for him, etc. If he's a good guy, he'll play along and have fun with it and you'll both enjoy a few laughs.
Act like children
You don't have to be so serious anymore. Dates are about having fun, and if you feel uncomfortable in an expensive restaurant or an opera theater then you shouldn't go there. Try going to a playground and swinging on the swing set together. Climb trees and get a little bit dirty. If your attitudes can be loose, you'll find out right away if you've found the right type of person for you.
Be cocky and self-deprecating
If you're a guy who wants to make a good impression on a girl, you can't be too serious. Women want a man who can make them laugh. So when you joke around, ride that fine line between arrogance and insecurity. Never let either be serious confessions though -- keep it silly. If you can be both cocky and self-deprecating at the same time, the result will be humorous.