So, you’re here to learn how to flirt! First, lemme say this: this is for guys who want to truly, sincerely, exclusively give your time and attention to one woman and want to attract her in a way OTHER than just swiping right, sending naked pics, and other unsavory activities.

If that sounds like you, well, you’ve come to the right place. (I am not interested in helping manipulators, pickup artists or other gross and sundry dudes.) 

And for meeting the right girl, you gotta know how to flirt. In person..

How?!! What if you’re socially awkward? What if you are nervous or insecure or just don’t want to be shot down? You gotta let that go, guys. Be prepared for rejection, and, if it happens, shrug and move on to the next. You can’t pin your ego or your identity to being accepted by everyone out there, or you’ll never leave the house. Like these guys.

So! Wanna leave the house and meet a great girl? First, don’t just read a bunch of the nonsense online, written exclusively by dudes, about how to flirt with a woman. It’s full of horrible advice. This column has some pretty good ideas, but it’s the rarity. Instead, trust a girl who has been flirted with both poorly and excellently over the years, that there are things you can do to improve your chances and help you not look like an idiot doing it. Let’s go.

Wear a henley. No shit. Trust me: women LOVE a guy in a henley. I myself can’t resist' ‘em. And, if you want to dress it up, throw a blazer over it and pair it with some nice jeans. And, while you’re at it, get yourself a nice big watch. Doesn’t have to be designer or anything, just a nice, big watch. And a nice, big watch with the henley? Yum-me.

While on the subject of wardrobe, go easy on the jewelry. A subtle necklace with the henley might be nice, just make sure it’s not a reject from the Liberace House of Crap.

Know just the right amount of cologne to wear. If you over-do it…eww. A survey of my friends decided these are among the best ones: Gucci for Men, Emporio by Armani, and Polo Black. Also these and some other favorites, like Creed-Green Irish Tweed, Silver Mountain Water, or Millisime, can be found here for a more reasonable price.

Stand up straight. This can serve to make you feel more confident and might just fool the ladies into thinking you are. Plus, good posture is so sexy. If you need a visual example to follow, this might be the only reason I would ever tell anyone to watch Entourage. Adrian Grenier does it right.

Walk up to a woman, smile, and say hello. She will say hello* back. *An aside: if she doesn’t, if she frowns or turns away or in any way acts not interested, leave the woman alone. Full stop. Okay, back to the scenario.

If you’re shy or nervous before all of this, practice it. Literally, practice. At home, in the mirror, with a trusted friend or pet. Say it aloud. Try this.

After the hello, say, “I know what you’re thinking.” Followed by something completely unexpected, odd, maybe even ridiculous. Reference the surroundings, the drink in your hand, the outfit you’re wearing. Be a tiny bit self-deprecating or completely over-the-top braggy. Why does this work? Because it’s cute, it’s irreverent, it’s totally out of context, and it’s silly. All of these things are adorable.

I promise you, she will laugh, even if what you said is a tiny bit goofy. Tiny bit goofy is better than puffy arrogance. Once she laughs, give her your name, shake her hand, and BAM you’re in a conversation. And, if you offer to buy her a drink - which you do NOT have to do, but doesn’t hurt - she’ll probably say yes. There. You’ve extended your conversation. Make it count.

The whole time, follow these rules:

Be confident but not cocky. Talk about yourself a bit but ask her questions about her, and listen to the answers.

Look her in the eye but don’t stare. This is simple. Just look away every 10-15 seconds by glancing at your drink or down at the bar top (NOT all around the room or at other girls). Then look back at her. You will come across like a more interesting person yourself, and she will feel those tingles of someone finding her attractive. Those tingles are what it’s all about.

Be funny. Easier said than done, right? It can actually be learned. Watch comics who are truly funny, like Jake Johannsen. What makes him funny? His storytelling, his timing, his observations, all of it. I used to teach him in my classes as an example of a funny storyteller. Pay attention to your funniest friends and see what makes others laugh. Get some good one-liners and practice them beforehand. This site is also a great place to start learning how to be funny.

Be sarcastic, a bit sardonic, and witty, but not cruel.

Don’t take yourself too seriously.

Compliment her. Make her feel good.

DON’T do “negging,” which is that horrible thing of insulting her so she’ll want to prove you wrong. Nope, nope, and nope. It’s gross, it’s offensive, it’s manipulative, it makes you a creeper, and any girl with any sense will walk away from you, if she doesn’t actually RUN away.

When it is time to ask her out, again, be confident but not arrogant. Simply, you know, ASK HER OUT. “Can I take you to dinner” are some of the nicest words a woman will ever hear. Ron Livingston does it right in “Office Space.”

Once you have the date, check out my piece about how to keep a great girl (in a relationship, not your basement).

Now go forth. Flirt like a champ.

VV