Pick Up Tips for Guys: Find a Wingwoman


Guys, it true. The best wingman is a wingwoman. Having a girl on-hand makes you automatically look less like a skeevy pick-up artist out on the prowl, and a whole lot more like a sensitive, mature, thoughtful young man capable of a serious relationship. The fact that there is a girl (who is not sleeping with you) willing to vouch for your trustworthiness makes us 100% more willing to talk to you, and, perhaps, if you play your cards right, make out with you a bit in a back booth. (We know this sounds crazy, but believe me, this is really how women think.)

Though it is common knowledge that women make great accessories when you are trying to pick up girls, there are certain types that make great wingwoman, and there others that don’t. That’s being said, there are pro’s and cons to all.

 1.    Your Sister

PRO: She knows you, your background, and she can vouch for the fact that you are definitely not a serial killer (we hope.) The mere fact that she would now be willing to hang out with you now, even after you teased her mercilessly for the last two decades, shows the depth of your current maturity.  Plus is makes you look sweet and family oriented; girls like that. It makes you look vulnerable and therefore more attractive. Kind of like when you hold a puppy.

CON: She’s your sister. Unless its your hometown bar and it’s the Holiday break, we kind of wonder if you have any friends that aren’t related to you. Plus she has way too much dirt on you. Though that story of how you wore pink bunny pajamas until you were thirteen may seen funny to her, it may not necessarily reflect your suave new image.

2.    Your Ex

PRO- She knows you, she can vouch for the fact that you are a great kisser (and more), and the fact that you are still friends after you broke up puts you in a really positive light.

CON- You broke up for a reason, and the hottie at the bar is probably going to ask what that reason is, because the two of you seem like such great pals now. Make sure you have your stories straight first, lest she share that the REAL reason you broke up was because you slept with her cousin at her grandfathers funeral.

3.    Your College Roommate

PRO- The fact that the two of you lived together for all of senior year and didn’t hook up says that you can at least see a woman as more than a sex object, and value a relationship with her based on her friendship and intelligence. Plus the two of you have a great repore based on many a drunken night together.

CON- Um… Why exactly did the two of you never hook up? Is it because she turned you down, or because you aren’t into her? Before you enter into any sort of wingwoman relationship with her, make completely sure that neither of you are harboring any sort of long-suppressed feelings for each other more than friendship, because someone could really end up getting hurt.

4.    Your Hipster Lesbian Friend

PRO- She’s the best of both: She thinks like a guy, but understands women in a way you never could. Plus, there is absolutely no chance of you two ever hooking up. As an added bonus, she knows first hand what pick-up lines work, and maybe she will share some of those with you.

CON- Her moves are a lot smoother than yours, so make sure she doesn’t cock block you!

5.    Your Mom

PRO- Believe it or not, I have actually seen his one work. Your Mom, if she agreed to accompany you to a bar, is probably a pretty cool Mom. Moreover, she is the one woman in the entire universe who thinks you are the handsomest, most charming, intelligent boy that ever lived. (Plus, she has a vested interest in you meeting a nice girl, because she eventually wants Grandkids!) And if you are seen escorting your Mom out for the evening, and you treat her like gold, that is a major turn on to girls. We like to see you being sweet.

CON- She’s your MOM. ‘Nuff said.

Overall, its up to your judgment. We hope, by this point in your life, you have some friend, that is female, who is willing to help you find a date.  Platonic relationships between men and women are a great way to learn about the other sex in an easy, non-threatening environment, and you can learn a lot that you can put in to practice when speaking to potential dates.

So next time you are going out on the prowl, leave your frat brothers at home and bring one of your girls. I think you will find it does wonders for your game.