How to successfully flirt

On the street

Daylight can be daunting: You can’t rely on dim lighting, loud music, or alcohol to mask mistakes. On top of that, most women aren’t exactly on the prowl while they’re at the grocery store or walking down the street. But that doesn’t mean she’s not open to a daytime pick-up, assuming your game is tight.

Open with a compliment: Pick-up lines — even playful ones — can come across as too strong for the harsh light of day. Instead, open with a little light praise, Flicker suggests. “You can’t go wrong with a sincere, classy compliment,” she says. “Tell her you love her shirt or her hairstyle, not her cleavage.” Worst-case scenario: She’s not interested, and you walk away looking like a really friendly guy.

Don’t be afraid of rejection: To quote Wayne Gretzky, you miss 100 percent of the shots you don’t take. While hitting on someone in broad daylight in an atypical location is risky, and perhaps the most likely scenario for rejection, trying anyway is great practice — and a solid way to inure yourself against negative outcomes. “Nobody likes rejection, but you can’t be afraid of it or you’ll never move forward,” Flicker says. Besides, you never know when you just might connect with someone.

At work

Office romances are tricky, but that doesn’t stop 39 percent of workers from trying them out anyway, according to a recent survey by And really, the workplace is a great place to meet smart, ambitious women. Catching her eye in a professional setting — without getting slammed with a sexual harassment suit — is easier than you think

Focus on yourself: “In any professional setting, you need to be the guy who stands out,” says Grant Cardone, author of If You’re Not First, You’re Last. “Confidence is, and has been for the last 200 years, what people look for in partners, whether it’s the group looking for a leader or a woman looking for a man.” Instead of worrying about what she’s looking for, focus on leading and dominating in the work place. She’ll have no choice but to take notice.

Focus on work: “The office is hard, because you don’t want to come across as creepy,” Flicker says. “Ask her about a project she’s working on. If she engages, she’s interested. If she answers — but it’s short, or she brushes you off — she’s not.” Remember: It’s better to err on the side of caution when it comes to work. So even if she seems interested, wait until you’re both off the clock before you ask her out.

Know when to lay off: “Never try to pick up the wait staff,” says psychiatrist and dating expert Scott Carroll. “They’re working and are often just being nice because they don’t want to get fired. If they’re interested in you, they’ll go out of their way to let you know.” Same goes for sales associates, baristas, bartenders, and customer service reps.

At a club or party

Good news: If she’s at a bar, club, or party, she’s probably open to — or even looking for — something. “People take more risks at night, so the bar scene is a little easier to navigate,” says Flicker. But it can also be more difficult, since she’s mentally prepped herself for a long night of getting hit on and subsequently shutting guys down.

Be a magnet: Instead of cornering her at the bar and hitting her with your best line, focus on being the life of the party. “Go with friends, have fun, and talk to everyone around you — girls and guys,” says Carroll. “The point is to be cool and fun and never look like you’re trying to pick anyone up.”

Use your environment: Your surroundings dictate whether you come across as dashing or desperate, says Los Angeles-based marriage and family therapist Allen Wagner. “What’s seen as innocent or casual during the daytime, such as taking a walk, can have unintentional implications after dark, when a woman must determine whether it’s safe to separate from her crew,” Wagner explains. “For example, you can be bolder at a house party, because it’s a closed event.”

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