I'm what you called a "serial dater." And, thanks to my experience in the dating realm, I've perfected not just the art of the awkward and intimidating first date, but those "Where is this relationship going?" meetings that follow, as well. Oftentimes we're so consumed by the first date, that we forget that second dates are an even higher-stakes game — you've made a good enough impression for a person to call again, but will this lead to more?
After the initial nerves of the first date wear off, second dates can actually be more of a thrill. They're also a lot more fun to plan. You've learned the barebones of your partners interests and have the ability to play to them in one magical night. It sets the tone, in ways, for the kind of relationship you might envision with that person — who knows, maybe that late-night karaoke session will end up being the date the two of you recall to your friends as the moment you knew you were head over heels for each other.
Of course, some of the best dates happen in the weirdest of circumstances, or with no real plans at all (True story: The best date I've had in New York was a stroll down Super Bowl Avenue in Times Square accompanied by late-night games at Dave & Buster's). But, after a while, I inevitably fall back on my list of my spots guaranteed for a good time (No, not that kind of a good time). A second-date spot should be comfortable, adventurous, and out-of-the-box enough to keep them intrigued — and with these ideas, they’ll without a doubt be wondering by the end of the night just what else you might have up your sleeve.