Dating in this city, or just meeting new people platonically, is no easy feat. Whether you're spoken for, in the midst of a passionate affair, or simply tired of the same ol' routine, it's not easy to put yourself out there in a jungle like this one. Thus, I've made it a Summer resolution to speak to some of the city's most interesting fellows about what it's like to date in New York or, if all else fails, how to keep your network fresh. This is not a wistful Carrie Bradshaw-inspired column, but rather a fun way to get inside the heads of NYC's cutest (ahem, coolest) guys.

First up: Jerry Guo, cofounder of Grouper. Guo started the online "social club" (read: it's not meant as a dating site) with his best friend, Michael Waxman. The two met while at Yale and now find themselves in pursuit of startup success just a couple years out of undergrad. Grouper's concept is to bring together three guys and three girls in a rad New York setting (they do all the legwork of matching up one group of friends with another, finding the locale, and setting a date) for drinks, conversation, and, if all goes well, a followup hangout.

When I met Guo, I wasn't sure what to expect, but he's everything a worldly gentleman who finds himself pounding the startup pavement should be. Fun fact: Guo and Waxman move apartments every month, so they have a new "lease" on a neighborhood, which makes it exponentially easier to explore, scout new Grouper meetup locales, and learn more about the city they live in. Here's what Guo had to say about Grouper, and how to keep your social life exciting in a city equally as exciting.

PopSugar NYC: Tell me as simply as possible — what's Grouper and how does it work?

Jerry Guo: This is a new type of social context. You and your two friends can meet another group of friends, and it doesn't have to include the awkwardness of browsing through profiles and setting something up. We do it for you, and it's seamless. We're not a dating a site, that's definitely something I want to get across, but because a lot of our members are in their 20s, many of them happen to be single. Some Groupers have ended in couples, but the cool thing is that the majority of the time, these new groups have all hung out again. We think that online social interactions have become increasingly categorized into buckets — "this is a date," "this is networking," and "this is me making friends" — and it doesn't have to be one or the other. It can be everything, and the best type of connections are made when it's not forced.

PSNYC: OK, so Grouper isn't a dating site, but you say there have been cases where people have coupled off. What's Grouper's success rate?

JG: I make sure to go out of my way not to be creepy, so we try to stay out of the next steps. We don't have a survey that asks if anyone is dating after a Grouper meetup. But we definitely know that over half of the groups will have a followup hangout outside of Grouper and at least a handful of people are now dating. Because we don't view ourselves as a dating service, we don't keep track of the dating statistics. For Grouper, it's about managing expectations. I want people to know that we're not psychic, we're not Patti Stanger trying to find your perfect match. What we do is match compatibility based on the information you provide in your Facebook profile [you sign up privately through Facebook].

PSNYC: You're banking on Grouper members to portray themselves in an honest light via their Facebook profiles then?

JG: Yes, we don't do the OK Cupid 30-minute questionnaire. There's been cutting-edge research that show that what you share on Facebook is a fairly accurate reflection of your personality.

PSNYC: Grouper sends its members to some pretty cool places around the city. How many NYC spots do you have under your belt?

JG: About a dozen. It's really fun to be the one that gets to go out and find these bars that are the best in the city — great vibe, great drinks — and usually, these venues will throw in some extras on the night of your Grouper meetup. We also want it to be a place that is happening while you're there.

PSNYC: Which bars do you work with currently?

JG: Apotheke, Blind Barber, Andaz Fifth Avenue, Cienfuegos, Hotel Chantelle to name a few.

PSNYC: What is it that you look for in the places you choose to scout for Grouper meetups?

JG: Our tag line is "Grouper features the most interesting people and venues in the city," so the place doesn't necessarily have to be high-end, it just has to have character. One example is Casa La Femme in the West Village — it's not really a part of the "scene" but it's in a cool neighborhood, there's belly dances and hookah, and I believe three out of the four Grouper groups that went there, the guys got up and belly danced. We want interesting places and makes it a cool experience on top of hanging out with friends and having fun.

PSNYC: Does your background as a former Newsweek foreign correspondent and lifestyle columnist help you navigate the city's best and brightest Grouper spots?

JG: Definitely. I wrote a weekly column called "The Good Life," which covered travel, hospitality, and lifestyle experiences around the world. I traveled to more than 40 countries, but NYC was always my home base. I think I've stayed in almost every boutique hotel in the city.

PSNYC: Do you have a favorite?

JG: I like The Standard a lot. The interior design of the rooms is very well thought out, and it doesn't hurt that there's Le Bain, too. I also really like the Mandarin Oriental, which I think flies under the radar in NYC. They have an amazing Asian fusion brunch where you pay $40 for a prix fixe meal, have an insane views, is literally right next door to Jean-Georges's restaurant, but I'd argue it's better.

PSNYC: If you had to set yourself up on your own Grouper "date," who would you go with, where, and what drink would you order?

JG: I would go to Cienfuegos — it makes me feel like I'm in Havana. And I would order one of the rum punch bowls. I'd probably bring a friend of mine who's a banker, but he's not your stereotypical banker. He came with me to Ibiza on two days notice, just quit his job, traveled to Wyoming, he's cool. And maybe a friend from work? We could be the travel nuts. For me, serendipity is a huge draw. I'd be attracted to a group of girls that are super passionate about something, are kooky. . . . One of the cool things about Grouper is that you can jump out of your regular social circle. I never get to meet people outside of my "world," so this is a way for people to break down the walls of routine.