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Flirting 101: When Is It Okay to Play?

By Gerry Strauss
Posted On May 17, 2021
Flirting 101: When Is It Okay to Play?

Our passions don’t die as we get older, yet the rules of engagement always seem to change. If you’re looking for flirtation without the disaster, follow these few simple rules. 

According to the Merriam-Webster Dictionary, flirting is defined as “behaving in a way that shows a sexual attraction for someone but is not meant to be taken seriously.” It’s a noncommittal toe in the pool to test out the temperature; a lick of the spoon to test the spiciness of a sauce. The whole idea behind flirting is to keep the tone casual and the stakes low. Yet, it still requires a great deal of courage, as anything less than a flirtatious response to your efforts can easily be interpreted as a personal rejection. On the other hand, a positive  reaction can be a huge confidence boost for both parties.

“If a woman signals to a man that she’s interested in him—or receptive to him—it diminishes his fear of being rejected,” says Neil Rosenthal, author of Love, Sex and Staying Warm: Keeping the Flame Alive. “She’s making it easy on him to pursue because she has already communicated her interest.”

During our teens and early twenties, flirting was simple because none of us had a clue what we were doing, where we were going, or where any of us would end up. People entered and left our lives a dozen times between happy hour and closing time, and the only repercussion for failure was counting the nights until we could give it another go.

These days, things are much different. Many of our contemporaries are married or in relationships, while others have simply lost interest in romance. Regardless, almost all of us have developed some sense of what we actually want in a potential mate. Today, we’ve all got (gasp) standards.

But what about those of us who still want to put ourselves out there and test the waters of attraction in a fun and frivolous way? That’s absolutely fine, but after a certain age it’s a bit harder to figure out with whom to flirt, when it’s appropriate, and how to pull it off without sending the wrong message.

First of all, what’s your strategy? According to top life and relationship coach Donna Barnes, a healthy dose of self-esteem is key. “Hopefully you get wiser as you get older, and you have more confidence,” Barnes says. “Confidence is very attractive, so never apologize for anything about yourself. What you may think is a flaw he may find sexy. Don’t think about whether or not he likes you, assume he does, and put your focus on finding out if you like him.”

Now that you feel ready to mingle, it’s time to find someone you like and test the waters. Obviously, this is easier said than done. Too much caution could relinquish you to the “friend zone,” but too much persistence could earn you anything from a dirty look to a restraining order. What’s the appropriate middle ground and how do you get there?

“The key differences between flirting and just friends are eye contact, leaning in, and touching,” says Barnes. “Lingering your eye contact just a little too long while smiling is the best way to let someone know you like them. Lean in with your body language—sit a little closer, lean in over the table, stand a little closer. Then touch them—on the shoulder, on the hand or arm, a gentle touch just to make a connection. Someone who is only interested in friendship should have healthy boundaries and stay out of your personal space.”

Pay attention to how closely he guards his “me space.” That perimeter means a lot, according to Barnes. “You always have to pay attention to the body language of the person you’re flirting with,” she insists. “If you’re leaning in and touching and he pulls away and doesn’t reciprocate, then he’s not interested. Don’t keep trying. Value yourself more than to go after someone who doesn’t want you. Never touch him sexually, say overtly sexual things, or reveal intimate sexual details about yourself—that’s not flirting, it’s inappropriate.”

Once you figure out how (and how not) to flirt, you also have to figure out when it may or may not be appropriate. As we get older, it becomes increasingly important to recognize when someone’s emotional baggage should mean “hands off”… at least temporarily.

“Do not flirt when either you or the other person is going through an emotional time,” Barnes implores. “Several of my clients have mistaken the emotional intimacy of being a confidante through a rough period as the beginning of a relationship. That is rarely the case. If the person you like is talking to you about their divorce, the loss of a parent, or the ending of a job, they need a friend. It’s inappropriate to flirt. And if you’re emotional, you’re not thinking rationally about who to be romantic with or process what you’re going through before jumping into a relationship.”

The most important ingredient to a successful flirtation is common sense. Appreciate what you bring to the table, then look for someone you’d like to share that table with. Flirting can be a game, but it doesn’t mean that you need to put on a show. Be yourself, pay attention to responses, and let chemistry do the rest. And let’s be honest: If someone you’re flirting with is giving you the cold shoulder, getting to know that person better doesn’t sound like much fun anyway, so it’s not usually too hard to move on and not look back.

“Assuming the attention is desired, it feels flattering when someone finds us attractive and appealing—and shows it,” Rosenthal concludes. “We feel complimented and desirable.”

All this said, you can skip flirting and approach whoever interests you in a straightforward manner instead—but where’s the fun in that?