Have you ever felt so comfortable around a man so quickly that you think you may have just found a new best friend? That’s sort of what happened when I went out on another date via OKCupid.com last week. He was the first guy that I wrote to when I signed up for the free online dating service. I was excited to go on a date with someone whom I had made the definitive first move toward. It was all part of my attempt to break out of my shy-girl shell. Our communication before the date was sparse and the banter was only okay, so I wasn’t sure how the date would be, but I thought, why not get to know someone new for a few hours? I met him in his neighborhood in uptown Manhattan. The collegiate type, he was dressed in a pair of leather flip-flops, cargo shots and a striped button-down with rolled up sleeves, and rocked a goatee. We found a cheap and tasty Middle Eastern joint for us to eat and chat, and the conversation just flowed. He told me about the crazy dates he had been on. I told him that men in New York City are just as (if not more) flaky online as they are in real life. We talked about everything from our various creative projects and career aspirations (he’s in pursuit of a Ph.D. in Molecular Biology) to our family lives (me — the immigrant daughter of divorced Caribbean parents, him — the son of a happily married interracial couple who in the Tri-State area). After dinner we strolled along the Hudson River, not ready for our many discussions to end (at least I wasn’t). Though maybe they should have. My brother always says that if two or more people talk with each other for long enough, their conversation will eventually end up on the subject of sex. The fact that I’m a relationships editor whose job requires her to think about sex makes this hypothesis even more likely. He asked what stories I was working on, and I just so happened to be working on a “Frisky Friday” about what women want more of in bed. Who knew that two people who’ve never met could spend more than an hour discussing oral sex? Once the ice was broken, we chatted for another hour about everything from exes to inappropriate love of cult films. Nothing was off-limits and neither of us was at a loss for words. Realizing that the sun had set and I still hadn’t actually written my story and that I had a long ride back to the belly of Brooklyn ahead of me, I asked my date to walk me back to the train. He sad that we should hang out again and I enthusiastically said, “Yeah! You’re fun!” While I hope we can chat again soon, I’m satisfied with the few hours of entertaining conversation that I had with a cute guy — one that I pursued. The greatest things that I’ve learned from online dating so far have been personal. I know that sometimes I speak and act inappropriately and rely on my being a cute girl to get a pass. So what if I spent a whole two hours talking about sex with a not-so-perfect stranger? It was fun. Isn’t fun what dating is all about?