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{{else}} {{/if}} {{/if}} Canada. Uniquely Canadian.
Conversation starters from the pros

Conversation starters from the pros

By Maggie Kim

Everyone knows by now that “Come here often?” doesn’t cut it when it comes to kick-starting a conversation. Never fear, tongue-tied singles: We’ve got a comedian, a former ambassador, a hairdresser, and others willing to spill their tips on chatting up (and dazzling) just about anyone.

Denise Fennell, stand-up comic and lead actress from the 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 his or her body that I can connect with; I look at 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 the person he or she reminds you of a certain celebrity and maybe continue the conversation by asking, ‘If you could be any celebrity, who would it be?’ You’d be surprised by some of the answers you might get! It taps into who a person really feels he or she is, or aspires to be. It’s about finding out what someone’s dreams may be. Then you can start connecting.”
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Jill Kargman and Carrie Karasyov, socialites and coauthors of the book, Wolves in Chic Clothing
Jill: “Eavesdropping can be a clever entry point into a conversation. Let’s call it the ‘accidental eavesdrop’ because you don’t want to be rude. But especially somewhere 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. It’s a good tactic.”
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, owner of Where Brooklyn At! clothing company and former NYC lounge owner
“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 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. 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: 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, clinical psychologist, syndicated national radio show host and author of Dating for Dummies
“Pick something in the environment around you that you can comment on; for example, say, ‘Isn’t that the ugliest painting you ever saw?’ It’s something another person can focus on, comment on, and it’s also non-threatening. Or just be bold! Once I was invited to a party. 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 no, but even then... so what?”

Paula Froelich, columnist for the New York Post and author of It!: Nine Secrets of the Rich and Famous That Will 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 requires listening. You may only be interested in his or her body, but you won’t get any closer to the body if you don’t work the brain.”

Maggie Kim is a musician and writer living in Seattle.

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