Young man holding bottle of beer and flirting with female bartender.
Teaching Yourself To Flirt Is Easier & Less Awkward Than You Probably Expect

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Flirting is one of those things that’s way easier said than done. Sure, you might love the idea of chatting with the cutie you just matched with on Tinder, but in reality, it’s hard to know what to say. I once had a full-blown emotional crisis when I couldn’t figure out which emojis to send to someone before I asked them on a date. OK, that’s a little dramatic — but my roommate did have to step in to help me out. It left me wondering, can you teach yourself to flirt? (Obviously, I’m asking for a friend.)

I reached out to relationship expert April Masini to get her advice on this. First of all, she says the key to knowing if you’re good at flirting is to gauge how the other person responds. “Flirting is supposed to be a way of connecting and engaging with people you find attractive,” Masini tells Elite Daily. “If they don’t connect and they don’t engage, and in fact, they disengage and distance themselves from you, you’re bad at flirting.” Or, on the other end of things, if you find yourself freezing up when someone flirts with you, you probably won’t win over their affection. “If you’re paralyzed by the sexual, romantic attention that flirting bestows, you’re going to fail at flirting,” she says. “If someone flirts with you, you have to respond positively for them to respond positively, in turn.”

As someone who once choked on my drink when a cute guy made eyes at me, I feel like I’m in need of this kind of useful life education. And dating coach Erika Ettin provides another point to consider: “If you are constantly being put into the ‘friend zone,’ then it might be time to assess your flirting ability,” she explains. Flirting should come naturally in a conversation, and when you’re good at it, you won’t even have to think twice — it will feel like second nature.

Lucky for me, and for all you other mediocre flirters out there, Masini and Ettin say it’s totally possible to teach yourself to flirt. Yay! But it’s going to require you to step outside your comfort zone a bit — here’s how.

Consider The Worst That Could Happen

Online flirt. Delighted female person looking downwards while talking per telephone and demonstrating her emotions


OK, I know this doesn’t sound like good advice — but hear me out. Masini says that considering the worst-case scenario can actually give you the courage to be brave. “Consider that you’re afraid of failure,” she says. “Once you recognize this, ask yourself what is the worst thing that can happen.” Maybe you won’t get a date, or you’ll be embarrassed, or you’ll have to face rejection… but a week from now, you won’t even remember those feelings. Masini explains, “If you break down this fear, and look at the worst-case scenario, you’re much more likely to overcome it.”


Now, some of these tricks only work if you’re flirting in person, and this is one of them. It’s simple but will take you a long way. “A great smile is the first sign that someone is interested,” Masini explains. There’s something about a genuinely joyful smile that draws people to you automatically. If you haven’t worked up the courage to go talk to that cutie, but you know you want to signal that you’re into them, flash them a huge smile to make the initial connection.

Live In The Moment

Happy romantic couple flirting while sitting at table in coffee shop


“Be present,” Masini suggests. “When you’re in the moment, you can really see and hear the person you want to flirt with, and that will allow you to be genuine.” Try not to think too hard about how you’ll come across. If you can notice little details about someone, it will help you connect with them more authentically. “The details can be the way they turn a phrase, the charm they exude to everyone, or something special they chose to wear,” Masini notes. “This will help you avoid pick-up lines that are stale, tired, and not winning.”

4. Talk About Things You Love

Whether you’re chatting online or IRL, Ettin says you won’t get anywhere if all you do is talk about work. “Playful teasing can be seen as flirtatious,” she explains. Ettin suggests talking about “travel, pets, and other hobbies,” because chances are, you’re passionate about these things. And your natural enthusiasm will shine through when you discuss topics that matter to you.

Lead With A Question

“Don’t walk up to someone and open the conversation with a pickup line,” Masini suggests. “Instead, start a conversation.” This applies to dating apps as well. While it might be tempting to drop a cheesy pickup line into their DMs, you’re much better off asking them a question about their day, their interests, or something you both have in common. This puts the ball in their court and leads to an open-ended conversation.

Use Your Body Language

Again, this trick works best if you’re hanging out in person, so it’s perfect to use on a first date. “Face the person full-on,” Masini suggests. This will show them that they have your attention. You can also touch each other casually throughout your conversation — a hand on the arm, or a squeeze of the shoulder. “Touching each other in non-sexual, but affectionate and communicative ways, are great flirting techniques,” Masini says. When you’re putting your whole body into the conversation, it elevates your connection.

Do Little Things To Show Your Interest

Friends meeting at a cafe


Here’s a tip you might not associate with flirting, but it’s actually one of the best things you can do to reveal your affection for someone. “Go out of your way to do little things for them,” Masini says. “Pick up lunch when you know he’s busy, bring her soup when you know she’s sick, surprise him or her with their favorite coffee drink, or offer to walk his or her dog if you know the other person is busy.” Sure, these acts of kindness might not seem like outright flirting, but they show your crush that you’re paying attention to what’s going on in their life.

The most important thing you can do is just to be yourself. “The best flirtation comes from within an organic conversation,” Masini explains. “So when you’re flirting with someone, structure the flirtation within a natural conversation.” Don’t think too hard about every little thing, and just enjoy talking to the person you’ve got butterflies for. When your authentic personality shines through, you’re most likely to attract the type of people you want to date. Breathe in, breathe out. Now get out there and show that hottie how you feel about them!

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