I was on a date with a beautiful 24-year-old Swedish woman in marketing who just moved into the city from the Hamptons. She got married a couple of years ago and was living in Southampton while her husband, a musician, traveled and had an apartment in the city. Because his schedule was unpredictable and he [...]

On Little Plains Beach last weekend in Southampton, a preppy blonde 29-year-old female friend in marketing meets my 32-year-old, Ivy League investment banker buddy. She tells him about how she believes women can be empowered and stay feminine. He says he’d like to get to know her better because he doesn’t meet any women who [...]

I was having drinks at Madame Tong’s in Southampton when I overheard the guy next to me telling a woman who he had just met that his girlfriend had recently broken up with him. He said that it was a shame that he had prepaid for them to spend a week’s vacation in St. Tropez [...]

I have a female friend in her late 20s who goes to the Hamptons every weekend to meet hot guys around her age, really hoping she’ll get married. What always happens is they dump her a few days after hooking up. I told her about another female friend who married a much older man who’s [...]

A friend’s 24-year-old sister visits the Hamptons one weekend and meets a 34-year-old investment banker from a really wealthy real estate family. He’s very excited about getting to know her so they set up a date for the following Saturday. He has a car service pick her up from the West Village to a helicopter [...]

Who: Christopher, Flying Trapeze Artist, 24
Likes: outdoor adventures (everything from fishing to camping to snorkeling), Dave Matthews band,  winning at poker, working out, BBQ-ing, driving, nice restaurants, Exercise Science , Oregon and obviously: teaching and flying on the trapeze and all things acrobatic.
Hamptons: Foodies, the Pizza Place, Pink Elephant, Stephen Talkhouse,  kayaking in the nature preserves, [...]

I recently touched base with a 48-year-old senior Wall St attorney friend who drives a new Porche GTR and rents a house in Southampton. He looks like George Clooney so he’s constantly meeting new women to date and has never been married. He said at his age he’d like to finally settle down and get [...]

My 32-year-old female friend who does marketing for a medical device company is dating a 27-year-old future doctor who’s currently in a residency program at Hackensack Medical Center in NJ. He works long hours and makes less money than she does but he’s going into orthopedic surgery for sports injuries so he will eventually have [...]

A friend of mine with a house in Southampton said he had a new friend, an attractive 28-year-old trade show model he met at The Javits Center. He invited her to come out East at the beginning of the summer season. He said they hooked up that weekend but then he decided not to ask [...]

Who: Sara, Sales, 24

Likes: fine dining, charity events, Penn Club, shopping, dancing, New York City, Westchester County, Greenwich CT, Bailey (my Cavalier King Charles), cream cheese, elliptical machines, FM 97.1, FM 100.3, FM 87.7, driving, girly TV, movies [...]