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in: People, Social Skills

How to Flirt Like It’s 1995

A man in a white shirt talks to a woman in dark clothing at a dimly lit bar; both appear engaged, exchanging classic 1995 flirting tips as they navigate how to flirt in the nostalgic nightlife setting.

A few weeks ago, I came across an article about how young people these days are tired of dating apps and want to meet romantic partners in real life. You know — the way people developed relationships in the good old days of the former millennium.  

The only problem? The kids today don’t know how to take part in the dynamic that kickstarts the in-person development of romantic relationships: flirting.

The Death of Real-World Flirting

Several factors have contributed to the lack of flirting ability among young adults.

The biggest one is smartphones. Because Gen Z and Gen Alpha have lived in a world where they could mediate all their communication through a device, many haven’t developed the social skills necessary for adept, in-person flirting. This has resulted in increased social anxiety when striking up conversations with potential romantic interests.

Dating apps have also exacerbated the decline in flirting ability. The nice thing about dating apps is that they guarantee initial, mutual romantic interest. You can only chat with someone on an app if they’ve also expressed interest. It takes the uncertainty and risk out of shooting your shot. When you flirt in real life, you don’t have the same guarantee. The person you approach may or may not be interested, and the only way to find out is by chatting them up and engaging in flirty banter.

COVID lockdowns didn’t help flirting skill development either. When I spoke with Jeffrey Hall, a professor of communication studies and the author of The Five Flirting Styles, he observed: “Post pandemic, there’s a lot of young folks who kind of missed out on some key developmental stages where you fall in love for the first time and interact with the opposite sex. A lot of young adults in their twenties right now, because of the pandemic, missed out on what it felt like to have those experiences.”

A final factor in the demise of flirting is the increased skittishness modern men feel as to what’s appropriate in terms of making romantic overtures towards women and what might come off as creepy or as sexual harassment.

To help young dudes who want to revive flirting and strike up relationships with women in real life, I took a deep dive into the research around this timeless skill. Here’s what I learned.

What Is Flirting?

Researchers define flirting as a mix of verbal and nonverbal behaviors that express attraction and gauge the other person’s receptivity to a romantic relationship. A coy smile, a playful tease, a casual lean forward, a compliment — all are flirtatious signals across cultures.

Here’s an important thing about flirting: it’s usually ambiguous. When you’re interested in a woman, you typically don’t just blurt out: “I think you’re hot and want you to be my girlfriend!” You’d risk immediate rejection from unrequited attraction. It would really weird the gal out. And it would be super ineffective: ambiguity is what makes flirting work and builds attraction; certainty is boring, while uncertainty turns our brains on and makes a situation or a person compelling.

The ambiguity of flirting allows you to show your interest without outright declaring it. It’s a way to test the waters in a low-pressure way. If the other person responds positively (smiles back, laughs, touches your arm), the flirtation can escalate; if not, both can save face by pretending it was just friendly banter.

There’s a thrill in trying to figure out if someone is picking up what you’re laying down. But because the uncertainty inherent to flirting is not just exciting but confusing, young people often want to avoid it. For those used to the security of dating apps, engaging in this dicey dynamic can feel too socially risky.

The 5 Flirting Styles

When we typically think of flirting, we think of it as something extroverted that you do in bars and clubs where you throw out pick-up lines with sexual innuendos.

Jeffrey Hall has found that’s actually just one type of flirting style among many.

Hall has identified five distinct flirting styles that people naturally tend toward. Understanding these styles can help you recognize your own approach and read others’ signals better:

  1. Traditional: Follows conventional gender roles where men initiate and women respond. Values courtesy but can lead to missed opportunities.
  2. Physical: Openly expresses sexual attraction through body language and touch. Great for quickly establishing chemistry but can come on too strong.
  3. Sincere: Creates emotional connections through meaningful conversation. Most effective for starting long-term relationships but can be mistaken for mere friendliness.
  4. Playful: Treats flirting as a fun game or confidence boost. Creates excitement but can send mixed signals about serious intent.
  5. Polite: Emphasizes courtesy, respect, and subtlety. Comfortable for everyone involved but often so subtle that interest goes unnoticed.

Based on Hall’s research, there’s no best way to flirt. All the different styles can lead to romantic relationships. The best thing to do is to lean into the flirting style that’s most natural for you. Doing so will not only allow you to be more authentic, which is attractive, but help ensure you find someone who’s compatible with you. If you have a sincere flirting style, you’re probably not going to get along with someone who’s a more extroverted, physical flirt. And that’s okay! “I wrote this book [The Five Flirting Styles] to my younger self because I wanted to know that the way that I communicated attraction was okay,” Hall told me. “You don’t have to be some suave, dashing guy to flirt effectively.”

These styles aren’t mutually exclusive. You might be mostly sincere with a dash of playfulness, or mostly polite but become physical once you feel more secure with someone.

If you want to know what your flirting style is, you can take Hall’s flirting inventory here.

Science-Backed Tips to Improve Your Real-World Flirting

Research shows that flirting is a learnable skill. Here are evidence-based tips to help improve your game:

Have fun and keep it light! This is the most important tip. Studies suggest a lighthearted attitude makes flirting more effective because it puts both people at ease. “When you have a mentality of being interested and excited about another person and just having fun with them, it shifts your perception and your behavior,” Hall explains. “Being present for the moment and enjoying the excitement of meeting someone who has romantic potential actually changes your nonverbal behavior. You can become more attractive in the eyes of the other person.”

Make her feel good about herself. Flirting is about expressing attraction, and it feels good to feel attractive! If you approach a flirtatious encounter with the mindset of helping someone feel good about herself, you’ll do well.

Start with basics. Smile and make (non-creepy) eye contact. Studies consistently show these simple signals indicate approachability and interest.

Use humor. Both men and women rate humor as highly effective in sparking attraction. Telling a funny story or offering a little gentle teasing creates rapport. Equally important: laughing at her jokes shows you appreciate her sense of humor.

Be a good social dance partner. Flirting is a social dance. Ask questions and show genuine curiosity. When she asks you a question, answer her and then throw the social ball back to her.

Mind your body language and create light touch when appropriate. Uncross your arms, face the person, and lean in slightly. If the situation allows, brief touches — like a tap on the arm when making a point — can enhance connection.

Show clear intent and follow up. If things are going well, you should segue into making your romantic interest more explicit. Hall’s research has found that “when you make very direct requests like, ‘I enjoyed our time together, I want to see you again, can I get a way to contact you?’ and the other person says yes,” it clearly shows that the flirting between you and the other person was indeed flirting, and not just friendly banter. “It says, ‘I’m interested in you as a person for romantic reasons, not just having a nice conversation.’ Showing clear intent can help you avoid the friend-zone.”

Also, make sure to follow up if there’s mutual attraction. “Lots of young women’s complaints about men’s behavior on flirting is men don’t follow up,” Hall says. While men often think they need to increase their allure by playing it cool and making a woman wait to hear from them, this isn’t the case: “There’s very clear research that being consistently available, showing clear interest repeatedly in a woman when there’s mutual attraction is key to creating a romantic relationship.”

Will a Man Come Off as Creepy If He Tries to Flirt With a Woman in Real Life?

A lot of young men hesitate to flirt in real life because they’re afraid they’ll come off as creepy. Hall says this worry is unfounded:

“If you’re worried about coming off as creepy, then you’re probably not the creep. Creeps don’t think that they’re being creepy. If you’re concerned about whether you’re coming on too strong, that’s okay. It means that you’re actually aware that how you treat another person matters. You’ll be fine.”

Just observe how your overtures are received, reading a woman’s signals as to whether your advances are welcome or not, and proceed accordingly.

How to Tell if a Woman Is Flirting With You

Flirting is a social dance, but how do you know if someone wants to flirt with you? It’s hard! Research found that men correctly spotted flirting only 36% of the time.

Signs a woman might be flirting with you include: frequent smiling and laughing (especially at your jokes), maintaining eye contact or making coy glances, finding reasons to be physically close or lightly touching you, playful teasing, asking personal questions, and offering compliments.

The key is looking for multiple signals appearing together over and over again. One smile doesn’t mean much, but if someone is laughing, leaning in, making eye contact, AND asking about your weekend plans — that’s strong evidence of flirting.

Make sure to check out our detailed article on how to tell if a woman is interested in you.

Conclusion

If you’re a young dude wanting to meet women out in the real world, you’ll need to up your flirting game.

As Hall advises, “This is truly some of the best stuff you’re ever gonna do in life. So prioritize it — even when you’re like, ‘I could go out to this party and there’s new people and it could be uncomfortable.’ Go to the party anyway. Everyone feels uncomfortable when they’re talking to new people. Do it anyway. The stakes aren’t nearly as high as you’ve imagined them to be. And it’s fun!”

So get out there and practice. Strike up conversations at coffee shops, bookstores, or social events. Start small with a simple smile and hello and see where it goes from there. Keep your flirting light and fun and don’t worry about the outcome. By doing so, you’ll paradoxically find that romantic success naturally follows.

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