How to Avoid Looking Desperate when Flirting

She was sitting down at a Chicago jazz event, and she kept looking at him. When she wasn't looking at him, he was looking at her. When both of their eyes met, they'd immediately look away. She left without his number and was disappointed. He left not knowing she even wanted his number and wasn't in the mood for rejection. Both single people lost out on a potential match. But how would they know the other person was interested without looking desperate?

Location can be the best reason to approach a person without looking desperate. For example, the Hyde Park Alliance for Arts & Culture had a jazz event on Fri., June 11, from 8 p.m. to midnight called "Cocktails and Clay." Both singles and couples showed up to enjoy the music and a 45-minute clay class in one of the art rooms near the center of the building. It was obvious who came out for the music, the art and the people just from some of the outfits.

In a place like the Hyde Park Art Center with art, liquor and music all over the place, it's fairly easy to find something to talk about. A conversation could spark up by standing next to the person and complimenting the art on the wall or asking if he's enjoying the music. If both the guy and girl were mingling by the refreshment area with the bartender in the two back rooms, a simple question like, "What are you going to get? What's a tasty drink tonight?" could lead into more conversation.

Pick-up lines should die a slow death in a singles' scene. They usually make the person saying a pick-up line look corny. Pet names are shaky, too, for women (or men) who don't really like you calling them "baby" and "honey" when the other party doesn't even know how to pronounce your first name. But a casual conversation about something in the area can always be a good way to warm up a longer conversation.

Here are other ideas to spark up a conversation in other Chicago locations:

Bookstores like Barnes & Noble or Borders Books, Music and Cafe: Stroll over to the person and mention how good the book is, ask for a book nearby the person and ask if he's read it, or ask what was the last book he read and did he like it.

Chicago lakefront: If you're on a bike, this may be a little harder to do. But you could always walk over to a person sitting by the rocks facing the lakefront or walking or jogging on the bike path. Mention how beautiful the weather is. Compliment the shoes he's wearing.

Coffee shop: It's fairly easy to spark up a conversation if it's crowded. You can always apologize for the crowd and ask can you temporarily sit there if he's sitting alone. Or, sit at a nearby table and smile. If he's got a book, magazine or drink in his hand, ask about it. If there's music in the background, compliment it if you like it or say something like, "This music would be better if it was _________." You can find out his musical taste from that.

At a stoplight leading to Lake Shore Drive or I-94: Do not crash trying to flirt! Make sure you're really at a complete stop. Men usually love cars and motorcycles. If you compliment their rides, it's about equal to him telling you he enjoys your company or complimenting your outfit. If you like cars too, huge bonus because now you can say something savvy about your car knowledge. Don't ask anything too detailed or like you're trying too hard. Keep it light. Compliment the color scheme, the spinners or wheels, the body of the car or even the interior if you're close. If he's interested, he'll pull over. If not, pull your shades down and drive off. In a car, you don't even have to walk away uncomfortably.

Museums/Aquariums: He's clearly into art and history if he's strolling around the Shedd Aquarium, the Museum of Science and Industry or any place like that. You can always walk over to the exhibit he's looking at and point out something on display.

Post Office: Chicago post offices are notorious for long lines. Some people come in with mp3 players or books in hand because they know it'll be a long line if they're not picking up a package at the window or using a postage/package credit card machine. Try not to complain to start a conversation though. Play dumb and ask the person how to fill out one of the postage forms. Let that segue into a conversation about whether this person lives in the area or if your package is really interesting, try talking about that. This one may be shaky though because if he's not interested, you still have to stand in line in front or behind him. If he's not interested, get those headphones ready or that book to hide your face.

There are plenty more places in the Chicago area that can spark up a conversation just from the objects surrounding the area. Keep the conversation casual. Make sure to smile and make eye contact. If you're in a pack of friends, take a moment to stroll alone so he doesn't have to risk being ridiculed by your crew. If he doesn't engage in conversation with you, walk away nonchalantly and don't get mad about it. Not everybody who you're attracted to will be attracted to you. He may have a girlfriend or boyfriend. Or, maybe he's just not in a talking mood. But there's always next time and next location.