What Guys Get Wrong About Flirting
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What Guys Get Wrong About Flirting
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What Guys Get Wrong About Flirting

4 Flirting Mistakes You Probably Make Without Realizing

Done right, flirting is a ton of fun.

When two people are attracted to each other, simple acts like joking, laughing and looking each other in the eyes can feel like magic. Flirting has the potential to lead to a date, a hookup or even a beautiful long-term relationship.

Done wrong, flirting can be a nightmare. It can be awkward, unfunny, cringe-worthy, painful, and, in some cases, downright terrifying for the intended recipient. It can also lead to being ignored, blown off, unfriended, blocked, or even with a drink right in your face.

RELATED: The Art of Flirting Without Negging, Explained

Flirting is a tricky thing, and frankly, lots of guys aren’t that great at it. However, that’s not exclusively their fault. If you think about it, there’s not really any widespread education in how to flirt, leaving you to your own devices with a hope you’ll figure it out.

But since lots of guys — particularly men who flirt with women — don’t actually know what women want, they’re at a distinct disadvantage when it comes to flirting. To help you sort it out, we spoke to a handful of dating experts, as well as some real people with real-life flirting horror stories, to nail down some common flirting mistakes you should stay away from (and how you can up your flirting game as a whole).

Flirting Approach

“The sun shines every day and men flirt with me in ways that make me uncomfortable.” - Kate, 29

While there are many different ways you can screw up flirting, perhaps the worst one is flirting in situations where you shouldn’t be. Guys can easily creep someone out by flirting with them in a professional work setting, for starters. Not only is it most likely unethical office behavior that’s more likely to unsettle the other person than get them hot and bothered, it’s also a good way to find yourself on the wrong side of a harassment complaint.

There’s also the problem of faking it. If you have low self-confidence, it might seem tempting to put on a persona that you think will appeal to someone you’re interested in. But nothing could be further from the truth, according to Jess O’Reilly, Ph.D., host of the “@SexWithDrJess” podcast.

“Don’t try to be something you’re not,” she says. “If you’re not goofy, don’t try to be in order to attract a partner. If you’re nervous, don’t act overconfident. Communicate in a manner that feels natural to you. If you’re more of a non-verbal person, use your facial expressions or body language to convey interest. If you’re good with your words, send them a thoughtful text before you meet up. If you like to joke around, be playful and don’t take yourself too seriously.”

But let’s say you’re in a situation — at a party or social event, bar or club, or in an online dating scenario — where a degree of flirting is expected (and even encouraged). You’re not trying to be someone else here ... so what should you avoid doing?

Flirting Mistakes

1. Being Overly Romantic

“I went on a date with a guy who said, ‘You know, you're sitting next to your future husband.’ I replied, ‘You know, I'm not.’ Not because it was our first date that he didn't bring his wallet for, but because ‘Will you marry me?’ is a question, not a statement.” - Alli, 36

For many people, the end goal of flirting is to find a long-term partner. You might not be looking to lock it down right away, but that’s the hope — you’ll meet someone and through your flirtations, convince them to give a relationship with you a shot.

However, that doesn’t mean you should bring that full-throttled romantic approach to your flirting. For starters, you’re likely to turn someone off who is trying to start off more casual. Even a fellow story-book romantic is likely to want a bit more time to get to know you before things get Hallmark-card cute, too.

Another aspect of that is remembering not to get too complimentary. That doesn’t mean you should be negging, but you definitely shouldn’t mistake fawning for flirting.

“[Men will] say, ‘Oh my gosh, you are so gorgeous, so beautiful, I can barely contain myself … you’re so stunning,’” says Connell Barrett, dating coach and founder of DatingTransformation.com. “When you fawn over the other person, you’re not flirting with the other person. You’re basically saying, ‘Hey, you’re above me.’ And it’s very hard to create attraction that way. We don’t want to date down! We don’t want to date somebody who fawns over us, we want to date someone who flirts with us. That’s how other people are going to look at us, as men.”

2. Acting Way Too Sexual

“This man who had once told me that we would have sex, if not that night, sometime in the future, was randomly standing at my street corner, looking at me very intently. He proceeded to walk beside me for 15 minutes despite me not wanting him there. I wasn't into him, and he was so adamant that we would have sex, it felt almost like a threat.” - Claire, 31

Not unlike being too romantic, being too sexual when you’re flirting with someone is also a terrible move. While premature romance can be written off as you being an old-school gentleman, bringing up sex before it’s appropriate (and without the other person asking for it) is a surefire way get yourself labeled a creep.

As much as sexual attraction is a huge component of the desire that pushes people to flirt with each other, good flirting keeps the rawer, raunchier aspects of attraction bubbling under the surface, powering the motor of the conversation without becoming the focus itself. You want to communicate to the other person that you are attracted to them without specifically saying just that.

One thing to stay away from, in particular, is unwanted touch. Lots of pickup artists suggest touching someone early in the process of picking them up to communicate your desire. This is a genuinely bad idea. While touch can communicate attraction, touching someone who isn’t expecting it or doesn’t want it only communicates an inability to understand boundaries or read social cues.

Barrett notes that guys should stay away from what he calls the “creepy hand of death” in particular.

“What I mean is if a guy has approached a person at a bar, he will put his hand on their lower back and leave it there way too long, making them feel uncomfortable,” he says. “It looks weird — like it’s a suction cup — and it makes the other person feel uncomfortable, and it doesn’t work. It’s OK to touch a person’s lower back in a momentary gesture of physical expression, but just leaving it there is not flirting, it’s creepy handsiness and socially awkward.”

3. Behaving Like a Stalker

“[One thing guys shouldn’t do is] directly reference archival tweets/Instagrams without having said social media accounts.” - Laura, 24

Like it or not, dating is digital now. People meet, flirt, fall for each other, talk, fight and break up on their phones. There’s no indication that this trend will phase out, and as great as online dating can be for helping people find each other, it’s also a source of a whole new set of problems when it comes to flirting.

“One of the main reasons why people have a hard time connecting in real life is because they are obsessed with their cyber 'social' life,” says Laurel House, dating and relationship coach and host of the “Man Whisperer” podcast. “Put your phone away. Stop using it as a crutch. It is not a wingman!”

That focus on the overlap between dating and social media can lead to all kinds of behavior that falls flat. That includes seeking out the social media accounts of people you find on dating apps and messaging them there. While it might seem like a good way to get around not matching with someone you find attractive, it’s really just a recipe for pissing off a stranger. You shouldn’t be trying for the hard sell, but rather approach situations where the other person shows some interest.

“Pickup artist culture has framed flirting as a manipulative behavior designed to swindle someone into hooking up,” says O’Reilly. “But flirting is about piquing a potential partner’s interest — not tricking them into liking you. Flirtation is an element of seduction, and seduction involves enticing for mutual measure — not manipulating someone into getting what you want.”

4. Being Too Demanding

“One dude asked me to help him learn to ride a bike via OkCupid. I said, ‘Uh, no’ but in nicer words. I think he may also have divulged that he lived in his parents' basement.” - Jess, 29

If you’re flirting with someone you don’t know very well, it’s important not to expect too much of them. What’s fun about flirting is a certain lightness, so naturally, expecting the other person to fill a hole in your life or be the answer to your problems is more exhausting than anything. House suggests trying to think of flirtation as making a connection rather than an avenue to something concrete.

“Flirting can be for the purpose of simply connecting and being open to seeing them and them seeing you,” she says. “Don’t consider it a pick-up. Consider it an opportunity to make a connection. Just the idea of 'pick-up' is intimidating because it has the pressure of successfully picking them up — which means what? Instead, you want to shift your perspective to making a connection. Just eye contact and a smile. That can be enough!

In short, expecting the other person to be or do something for you will probably end up with you being unmatched than with you getting what you want. Remember: Less is more in the early going.

“Flirtation is most exciting when it builds over time, so don’t try to do everything at once,” says O’Reilly. “Anticipation can be the most pleasurable part of hooking up (or dating), so take your time. Move slowly. If you’re flirting online, don’t start with sending or soliciting nudes. Be playful and patient.”

With that calm, slow and easy mentality, your flirting game can go from hurting your chances to helping them out in a big way.

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