How To Successfully Hit On A Woman Without Being Boring Or Creepy

by Courtney Brunson
Photo by Kalonji Allmond

I'm tired of hearing the phrase “hook-up culture” as much as I'm tired of living it. There's something slightly predatory about the way we approach dating and nightlife.

You go out, spot someone you wouldn't mind seeing naked and try to bang it out all within a 24-hour time span. No sexual tension, certainly no excitement and plenty of opportunities to seem like a poacher.

There is nothing fun about concretely knowing the outcome of an interaction as soon as you enter it. Asking for a number after 12 seconds could not be more awkward or obvious because dating is not hunting, and we've truly lost a handle on the art of how to flirt.

Creating a unique spark that stems outside the lines of a typical “Hey, can I buy you a drink?” pick-up line is rare, but memorable. There are a few methods to becoming more memorable and successfully hitting on someone without fail.

Photo by Kalonji Allmond

Eye f*ck

Consider eye-f*cking consent in the flirting world, and permission to introduce yourself while feeling invited to do so. Hold eye contact longer than you'd normally feel comfortable, and smile.

Repeat a couple more times until you've created a bit of tension and curiosity. If she is returning visual first base, then get ready to make your approach.

Master the "Three-Minute Connection"

Offering a drink to a stranger within the first moments of meeting her is creepy. Straight up. It's presumptuous and makes the woman feel obligated to reciprocate with her attention or interest. Basically you're saying, “Hello! I found you, and you are mine. I am going to penetrate you, but first have a drink.”

Instead, comment on what's currently around you -- like having a laugh at someone's insane dancing. You could even point out another couple who may or may not be hitting it off, and create a game out of an imaginary role-play of their conversation.

Seem like you're the type of person to strike up a conversation with anyone, not just a potential hookup. It's possible to create a connection by being fun and friendly WITHOUT acting like you're on a job interview.

No one has ever made my panties wet by asking what I do for a living, but non-traditional advances always stand out. Witty banter is the key to not only grabbing, but holding someone's attention.

Talk to her like you're making a friend instead of hoping for a conquest, and watch her drop her guard a little bit.

Allude to hanging out

When I say "allude," I mean really allude. Be vague and test the waters. For example, say you happen to be talking about museums. Bitches love museums.

Mention a cool exhibit you're looking forward to in the near future and what a great time you know it will be. Say, “We have to go; it's going to be incredible." Pay attention to her response, and then continue on to something else. Remain low-key.

Walk away

Once you feel like the conversation is going somewhere and you're vibing a little bit, walk away. Leave. Run off with the plug. Get the f*ck out of there.

Everyone knows the heart-sinking feeling of realizing a pursuer is not going anywhere. Between the body language and unwavering eye contact, we are terrified of those obvious signs that we are now "married" for the rest of the night unless a hasty escape is made.

A presence of attraction does not matter -- no one wants to feel trapped, and it's also pretty douche-y to monopolize a stranger's entire night. Even if you're a dime and some extra quarters, you will seem like a serial killer if you stay in a woman's face for too long.

The sexiest thing in the world is watching someone be social, friendly and the life of the party from the outside. For that reason, you need to scram a few minutes after making an initial connection, and let her see you have a good time. Give her air to breathe and space to tell if she's attracted to you. Give HER blue balls.

Leave with the perfect "goodbye"

Assume you've really got it bad. Her dumb jokes fill your heart with flowers, you both believe in aliens, and you've already visualized a night of Netflix and chill. It happens.

Before you're ready to head out with your friends, stop by the person one more time. Remember the fun event mentioned earlier? Say, “It was really great meeting you. I'll see you at the blah blah blah this weekend, right? Let me give you my Instagram handle.”

Confidently make it clear you will be having fun with or without her, but would like her company. Instagram swaps are also less aggressive than exchanging phone numbers, and more difficult to duck. (You can see when a DM is opened, after all).

More importantly, this is a sly way of offering up your cute selfies on a silver platter.

Erase all expectations

The best part about being friendly is you can make friends. I know, groundbreaking. If you enter a situation with low expectations, you will instantly put a cap on embarrassment or rejection.

Hey, you're just being sociable and have hopefully made an effort to strike up conversation with all types of people throughout the night. Even if you never see this girl again for the rest of your life, you had a fun and flirty interaction for a little while. Consider it practice for the next one.