The classic pick up and a classy pick up can be two different things entirely, the latter depending more on originality and authenticity than its clichéd counterpart. It takes not only courage but confidence to pull off the pick up, and to do it successfully, especially in a socially sophisticated spot like the Hamptons, is indeed an art form.
THE ART OF THE COMPLIMENT
"If I told you that you had a hot body would you hold it against me?" is only going to work if you've both been stranded in the arctic with a single sleeping bag. A come on with sexual overtones is best restricted to orgies and construction sites. Better to start with an opener which is germane to the setting such as "You've got a great swing," at a driving range or "I don't know how you can hold pigeon pose so gracefully," at yoga class or "I really enjoyed your essay," in a writing workshop. The key is that you're being honest because false flattery reeks of a hidden agenda. This sort of innocuous compliment also prevents any embarrassment if your target turns out to be taken.

THE POWER OF HUMOR
At the big boat party last weekend I saw two gorgeous girls on a Boston Whaler who jumped ship to join two guys posing as celebutante jail birds in blonde wigs and striped uniforms. The speed boat full of young attractive guys just looked at each other, like "What did we do wrong dude?" If you have a good sense of humor and don't take yourself too seriously and know how to have fun you have a good chance of finding someone to join in. If the first comment out of your mouth is negative "Boy this party sucks," it sets the tone. Would you rather date
Simon Cowell or Paula Abdul?
THE PERKS OF GOOD BEHAVIOR
I can't tell you how many times I see a guy trying to chat up a pretty girl but as soon as he gets in the drinks line will elbow her out of the way to get to the free champagne first. It's August. It's crowded. People are irritable. Why not be the guy or gal who stands out from the masses with unexpected acts of kindness and consideration? Do you want to be remembered as the guy who held the door for me when I had all those grocery bags or the idiot who pushed me off my pumps at Starbucks? The same holds true for ladies as well as gentlemen. The girl who is swearing like a truck driver at the valet parker is hardly making a good impression on any observing suitors she may meet later in the restaurant.

THE STRENGTH OF KNOWLEDGE
If you happen to be an expert on astrology it's alright to go ahead and ask, "What's your sign?" But it's best to develop your conversational knowledge base. Before you hit the benefit do a little research on the charitable cause. Going to the VIP tent at polo? Then learn a thing or two about the history and rules of the sport.
Little tidbits of useful information are great conversation starters. It helps to have a bit of local knowledge whether it is a great place to get a drink with a view of the sunset (East Hampton Point which has reggae on Sunday) or where you can park without a beach sticker (Bridgehampton High School has a shuttle to Sagg Main) or a hiking spot with beautiful vistas (Mashomack Park in Shelter Island).
People in the know are always popular, and it's also a way to start a connection that is not threatening. On the flip side, asking for a suggestion is another comfortable way to start a conversation, "Where's a fun place to go dancing?' or "Are there any public tennis courts?" or "Who do you think makes the best margarita out here?" Great intro and possibly a segue to a first date. As a matter of fact you have a handy tool right here on Hamptons.com to do your homework on hot Hamptons happenings.
THE IMPORTANCE OF HOW YOU SAY NO
I've seen it happen before – the snooty girl who is rude to the guy who approaches her only to later realize he's the host of the party she just crashed or her first interview the next day. Aside from the fact that you never know who someone is – it's just plain unattractive to be rude. It takes courage for someone to approach a stranger who has caught their eye. There are plenty of polite ways to let that person know that you're not available or interested – that you're waiting for your boyfriend or are enjoying a girls' night out catching up with your friends. That said, if the approaching person is drunk, rude, or a pest feel free to give them the boot.
So make the pick up more than about someone's genetically gifted or artificially enhanced body parts. Make it real. Be polite. Take a risk. And hopefully, with all your classy moves, get to yes.
Heather Buchanan is a bon vivant around the Hamptons and you can find more of her writing on love, life, and hot happenings at www.HamptonsHeather.com.