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Conversation Starters From The Pros


Everyone knows by now that “Come here often?” doesn’t cut it. To the rescue: A comedian, a bartender, a hairdresser, and others spill their tips on chatting up (and dazzling) just about anyone.

By Maggie Kim

Denise Fennell
Stand-up comic and lead actress from Off-Broadway hit, Tony n’ Tina’s Wedding
“The art of what I do, as far as improv, is about initiating conversation with strangers. I look at someone and try to find something on their body that I can connect with; I look at
“Don’t play it cool. Being intimidating and aloof is no way to start a dialogue, or a relationship.”
clothes—shoes, ties, whatever. I think guys find it endearing if you say something like, ‘I bought my dad the same shirt.’ It’s less of a come-on that way. I also think girls can get away with sillier things. I’ll stare at people until they notice me and say, ‘What are you looking at?’ and it totally works in terms of breaking the ice. You have to realize that the worst thing that can happen is he (or she) won’t respond and then you didn’t have a chance anyway—so you’ve got nothing to lose.”

Cristophe
Celebrity hairdresser to Bill Clinton, Nicole Kidman, and Liv Tyler
“Don’t play it cool. Being intimidating and aloof is no way to start a dialogue, or a relationship. Being casual and friendly goes a long way towards establishing trust with someone. Also, use the fact that everyone has an image or fantasy of who they are inside. Tell someone they remind you of a certain celebrity and maybe continue the dialogue by asking, ‘If you could be any celebrity, who would it be?’ You’d be surprised by some of the answers you get! It taps into who a person really feels they are or aspires to be. It’s about finding out what someone’s dreams may be. Then you can start connecting with them.”

Jill Kargman and Carrie Karasyov
Socialites and authors of the book, Wolves in Chic Clothing
Jill: “Eavesdropping can be a clever entry point to a conversation. Let’s call it the ‘accidental eavesdrop’ because you don’t want to be rude. But especially someplace like New York, where people are literally on top of each other, it’s easy to overhear something and join in with something fun and clever.”

Carrie: “Do something crazy with your girlfriends. My friends and I used to play a game where one of us would go up to a guy the other thought was cute and say, ‘My friend over there is psychic and we can prove it.’ We had a whole system worked out, but the guys would go along because they’re always up for an outrageous story.”

Danny Millan
Co-owner of the New York City café Kingsize and bartender
“Treat the person you want to talk to as a human being—as opposed to someone you’re trying to pick up. You can just say, ‘I’m not trying to hit on you, but you’ve got a beautiful smile.’ And if that’s the end of the conversation, let it be the end of the
“I think showing you have a sense of humor is a real door-opener.”
conversation. Be respectful and don’t force it. Everyone appreciates being told something nice, no strings attached. Be earnest, give a real compliment, and maintain eye contact when you’re talking. A woman can be wearing a low-cut top but make sure to talk to her—and not to them. Women are very quick to pick up on these nuances.”

Donald P. Gregg
Former ambassador to South Korea
“I think showing you have a sense of humor is a real door-opener. A willingness to be self-deprecating is often helpful. And remember that sometimes it’s a question of not saying too much—not falling all over yourself. Being low-key is good. And remember: The staring over your shoulder, or looking beyond the person you’re talking to as if to see who else is there—that’s a killer.”

Dr. Joy Browne
National radio-show host
“Pick something in the environment around you that you can comment on, like ‘Isn’t that the ugliest painting you ever saw?’ It’s something they can focus on, comment on, and it’s non-threatening. Or just be bold: Once I was in a party at a bar. I walked in and there were about 50 women—attractive, smart, well-dressed—but virtually no men. I walked up to the little cluster of men and said, ‘My friends and I are over there in the back, and they triple-dog-dared me to invite you guys over.’ The worst that someone can say is bug off, but so what?”

Paula Froelich
New York Post Page Six gossip columnist and author of It!: Nine Secrets of the Rich and Famous That’ll Take You To the Top
“Start with a compliment; there just aren’t enough compliments going around. A guy once looked at me and said, ‘I’m sorry to interrupt, but I just want to tell you I think you are really beautiful.’ It was short, simple and sweet and I was so flattered I was speechless, which rarely happens. But make sure it’s sincere and honest. Having a good conversation is about finding common ground, and that takes listening. You may only be interested in their butt, but you won’t get any closer to the butt if you don’t work the head.”


Maggie Kim is a musician and writer in New York City. She lives at MaggieKim.com. In answer to the question, “Come here often?” she replies yes.
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