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The 9 Girls You’ll Date In Your 20s (Represented by Pop Singers)

By / 04.03.14

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I started out trying to comprise a list of different girls that you’ll consider dating in your 20s, and realized they corresponded to the personalities of famous female artists. So without further introduction, here are 9 types of girls you’ll consider dating in your 20s, and the female artists that symbolize them.

1 Your Friend’s Little-Too-Young Sister – Selena Gomez

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No matter how young you are, Selena Gomez will always seem just a little too young for you. Maybe it’s because she started out on Barney and then the Disney Channel, or maybe it’s the fact that she dated another seemingly permanent 16-year-old Justin Bieber, but she will always seem exactly 16-17 years old. Like your friend’s younger sister, she’ll always be around, wearing a slightly uncomfortable amount of non-clothing, saying things that are just a bit too sexual.

Don’t date her unless you really think you can make a run at it, because you’ll always be uncomfortable, and jeopardizing the friendship you have with her older sibling. And of course make sure she’s of age. No one wants to take a seat from Chris Hansen.

2 The Partier – Miley Cyrus and Ke$ha When She Still had the $

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At some point (most likely in your early 20s) you’ll encounter the chick you meet at a club. It’ll start out as a one-night stand and will be great at first, because you’ll only be around each other when you’re having a fun night out getting drunk. She’ll belt out, “We can’t stop and we won’t stop” on a Monday night—but trying to keep up with the lifestyle will put you in both economical and emotional debt. And if done long enough will lead to unemployment and homelessness. Soon, the girl you thought you knew will go to rehab and start dropping the symbols from their name. (I never realized how much I loved the $ until it was gone.)

3. Peaked In High School – Carly Rae Jepsen

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“Call Me Maybe” was a jam that will not be forgotten, but perhaps Jepsen has already reached her peak. Girls who peaked in high school had the ability to turn down guys left and right because they were on top of the social pyramid, much like Jepsen probably had the ability early on to turn down artists trying to collaborate with her after the wild success of “Call Me Maybe.” But they will forever seek to find that amount of attention as they had when they were on top, only to find it’s not there anymore.

Jepsen is now considering writing a follow-up song to get people to remember both her and the chicks who peaked in high school titled, “Call Me Oh Please.”

4. The Driven Woman Who Is Way More Successful Than You – Beyoncé

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Beyoncé is a rare human specimen of science who has been blessed with a gorgeous exterior, an amazing voice, and an incredible ability to just get things done. Much like Beyoncé, the driven and successful woman you date will frequently make you feel like you’ve failed as a man. You’ll pay for meals you can’t afford, discuss world issues you don’t understand, and eventually see her leave you because “you should have put a ring on it.” I would have. I just couldn’t afford it.

5. High School Sweetheart – Taylor Swift

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Things were going smooth when you were seeing each other in the beginning, because there wasn’t much pressure then, and there weren’t very many people you could choose to date.

But within a few short months, you’ll know if you’re meant to see it through the “twilight” or go in another “direction.” It’s alright if it doesn’t work out, because you always had a feeling things would go Kanye West south anyways.

6. The Girl you’re In Love with but Constantly Get into Arguments with – Rihanna

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This is the girl you always wanted to be with, but when you got the chance to actually date her you realized you didn’t really get along that well. The arguments will begin over important stuff, but eventually you’ll start arguing over the littlest things like you took a “Which TV sitcom character are you?” quiz and you ended up getting manwhore Barney Stinson from How I Met Your Mother. Now, in a worst case scenario you’re a terrible human being who punches women, but as long as you can auto-tune an apology song out of it, all is forgiven.

7. One of the Bros – Hayley Williams of Paramore

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Hayley Williams of Paramore is so captivating that even chicks have crushes on her. She fits this category perfectly as being one of the bros. Hayley sings in a pop-punk band with a bunch of dudes, has collaborated with a famous rapper and DJ, and rocks the short hair-cut better than any girl I’ve seen. She’s the girl you shotgun beers with in college and meet 5 years later after you’ve “sold out” working for some corporate company. After she rocks your face off at a show, you find a way to meet her afterwards, where she reminds you how cool you used to be in college. After a moment of hesitation due to an early Saturday morning shift you’re supposed to work, she starts taking you places you would never go, like a restaurant that advertises baby lobsters and a dimly-lit bar where you have to out drink the local alcoholic “Townie Tom” to gain the respect of the fellow regulars. (They will one day get you out of a jam.) You’ll always end the night drinking on a rooftop somehow as the sun rises for the next day.

8. The Crazy Chick – Lady Gaga

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At some point you may have the unfortunate or fortunate opportunity to date an insane person. She’ll make you think everything’s fine at first by putting on her “I’m not crazy” poker face, but eventually she’ll be trying to walk down your wedding aisle in a rhombus shaped meat dress.

9. The One You Introduce to Your Parents – Katy Perry

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Now before you harshly judge me for this pick, just because she’s done songs like “I Kissed a Girl and I Liked It” (some creepier dads might be into that), and she has videos where her boobs are turned into various pastries or firework launchers, just remember that she is still at the core a preacher’s daughter, which essentially makes her a choir chick.

There are a lot of amazing girls out there and hopefully you find the right one. Just choose wisely out there on the dating turn table of love.

Toby Davis is a comedian originally from the plains of South Dakota and has been alive ever since birth. Follow him on Twitter here, or like his Facebook page.


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Toby Davis
About Toby Davis... Toby Davis has been alive since birth. Follow him on twitter for more laughs. Don't cost nothing.

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