#Love & Sex

How to Flirt Without Looking Like a Fool

by Hilary Braaksma

How to Flirt Without Looking Like a Fool

Whether you’re trying to get the attention of a romantic interest or you’re just trying to convince your dry cleaner to prioritize your last-minute stain removal, it helps to know how to flirt.


Everyone knows that girl who seems to be able to charm her way in and out of almost any situation with a smile or a funny one-liner. It’s an almost magical quality, embodied by people with no apparent pattern. So what is it that the charmers of the world have in common? They know how to flirt.


If you feel like it’s a trait you weren’t born with, don’t worry. It turns out flirting is actually a talent that can be developed. We talked to dating and relationship experts Shamia Casiano and Dr. Sheri Meyers about easy ways to develop your flirting finesse and navigate social and romantic situations without the fear of rejection. Here are 13 tips on how to flirt without looking like a fool:


1. Look at it as skill building. “Flirting is a real and important skill,” Meyers says. “Learning the art of flirting can help you in professional situations, it can help you melt boundaries between people, and it gives you a sense of your own personal charisma.” Don’t view it as the be-all and end-all to building sexual relationships but as a practical way to build confidence and make yourself more accessible to all types of people.


2. “Don’t put other people on a pedestal,” Casiano says. When you perceive somebody as more attractive, more successful or smarter than you, you’re setting yourself up for failure. It’s easy to inflate positive traits in other people, but try doing the exact opposite: Before approaching somebody, make a quick mental note of some of your own attributes instead of focusing on theirs.


3. “It all has to do with your ritual before you go out,” Casiano says. “Listen to a playlist that puts you in a zone of confidence. Invite all your girlfriends to get ready in one place. Bring your clothes and makeup, and get ready together to socialize and help build each other’s confidence.”


4. Practice makes perfect. “Flirt everywhere you go, but just a little,” Meyers says. “The more you practice in safe situations, the more comfortable you’re going to be in your own body and in yourself.” Start practicing with strangers at the bank or the grocery store before you work your way up to approaching potential partners.


5. “Don’t put all your eggs in one basket,” Casiano advises. When you practice flirting in your day-to-day activities, don’t worry about what will come of it. “It’s not about being attached to an outcome,” Meyers says. Flirt with abandon. If you’re not expecting every flirtatious encounter to turn into the love of a lifetime, the fear of rejection disappears.


6. If you’re too afraid to approach someone, start by flirting from afar. “Make eye contact and see if they meet your glance,” Meyers says. A gaze is one of the best ways to gauge interest, but take it easy. “You can feel when someone is looking at you, so you don’t want to appear psycho,” she says. Her advice? Make eye contact for two seconds, smile and then look away.


7. “The most important flirtation tool is your smile,” Meyers says. It’s a universal sign to other people that you’re open to conversation and you’re fun to be around. A real smile says you find joy in the little things, so a fake grin just won’t cut it. “An authentic smile is best,” Casiano says.


8. Channel your inner Beyoncé, or whoever you think embodies confidence. “When you’re first learning the skills, think of a character that might flirt really well and take on some of those qualities. I was a big fan of ‘Sex & the City,'” Meyers says. “How would Carrie flirt in this situation? Or how would Samantha do it?”


9. Flattery will get you everywhere. If you’re looking for an ice breaker, start by complimenting the other person on something you genuinely like or find interesting about them. Don’t overdo it; something as subtle as “I like your tie” can work. “A sincere compliment always feels good,” Meyers says. “It’s a win-win. The worst-case scenario is that you’ve done some good in the world by giving a compliment.” The best-case scenario is that you open the door to more conversation.


10. Ask open-ended questions. Conversation that invites only “yes” or “no” responses will fizzle quickly. Rather than asking “Do you like this song?” ask “What kind of music do you like?” or “What’s your favorite album?” And then listen and engage the way you might with a close friend. “Don’t be thinking of your next response,” Meyers says. “Really hear what they have to say and ask another interested question.”


11. “Don’t put on a show,” Casiano says. “If you have to have things prepared to say, that’s not good.” Let conversation flow organically, but if you feel it stalling, use it as an opportunity to excuse yourself to touch up in the bathroom or order another drink. Then take that time to think of something to say or assess whether it’s worth pursuing.


12. “Don’t overstay your welcome,” Meyers says. “Leave them wanting more.” Even if conversation is going smoothly, excuse yourself after 10 or 15 minutes. If they’re interested, it gives them an opportunity to ask for your number, and if they’re not, it saves you from potential embarrassment. If they want to keep talking, they will seek you out. “If you’re the initiator of flirtation, they need to be the initiator of follow-through,” Meyers says.


13. Don’t take yourself or any encounter too seriously. “Take everything with a grain of salt,” Casiano says. “There is a ton of dating advice out there that says ‘Wait three days to call,’ but if he really cares whether you called on day one or three, he’s probably not for you.” Take things lightly, and don’t be afraid to keep trying if it doesn’t work out. “If this is serious and intense, it’s not going to be fun,” Meyers says.


Check out more advice on flirting without looking like a fool from our relationship panel:





For more tips and personal coaching from Casiano and Meyers, go to shamiacasiano.com or drsheri.com.