1. The Chronic Self-Deprecator
She’s gone years without a main squeeze, so she’s channeled her frustration into a series of highly humorous but deeply cynical quips about life in general. She’s surprisingly easy to talk to, and before you know it you’re the last two sitting outside on the deck at the house party. And the awkward pause is properly capitalized on.
Things proceed nicely for awhile, until you realize this is a girl who can’t get out of her own way. Be it a particularly messy prior breakup or a deep-seated unwillingness to display a millimeter of vulnerability, you’ll eventually fall into a stagnated state of strife and frustration. You’ll leave with a bad taste in your mouth.
2. The Rule-Follower
She’s not so much prude as she is someone that holds herself and her boy-persons to high standards. There’s something incredibly adult about this relationship, given that the RF radiates with prospects of settling down and being an excellent mother.
She’s not exactly going to stay out until 5am, or spontaneously convince you to drop everything and drive down to Bonnaroo–and you’re at very high risk of turning into the “boring couple”–but this isn’t to say you won’t have a lot of fun together. If there’s a downfall here, it’ll come down along the lines of life getting in the way.
3. Girl Whose Life Peaked During the Age of BBM
Through a savvy combination of going on teen tours, having a strong association with colleges like Emory, Wisconsin, and GW, and having an irrational obsession with Betches Love This Site, she yearns for the days Murray Hill was still the “it” place for 20-somethings.
You date her for one of two reasons. One, because she reminds you of girls you grew up with. Or two, because you’ve never experienced the wonder of the Jewish American Princess & Associated Acts, and just can’t look away from the perpetual, spectacular madness.
4. The SheBro
She pounds shots, has too many opinions about the Red Sox, and her idea of a date is ordering in wings and onion rings. For the right type of man, she’s beyond a dream.
But the pitfall here is huge; she’ll often have a glaring lack of female friends. Which, as we all know courtesy of X Red Flags You Should Click On And Make Visceral Comments About, this will ultimately be the grand undoing.
5. Gloria Cleary
Gloria Cleary is Isla Fisher’s character in Wedding Crashers. Gloria Cleary, in addition to being as crazy as living in a world where a windowless box costs $1700 a month*, has this weird tendency to sometimes act like a five year-old. She loves to be spoiled, she’s emptying your wallet on things as worthless as antique gumballs, and you sort of hate her with a Lou Ferrigno-like passion.
[youtube=http://www.youtube.com/watch?v=392I_cnVbBI&w=640&h=480]
Which is exactly why it works. The sex is 1000 times better than even the most “so true” analogy from an article about things you must do during your first vacation as a postgrad.
*I totally got ’em.
6. Slang-Ridden Sasha
Despite having been raised in a comfortable suburb outside Illinois, SRS and her headband wearing ways are hellbent on being as culturally credible as possible. A hipster in the broadest sense, her life’s ambition is to be mentioned in the same sentence as Karen O. from the Yeah-Yeah-Yeahs.
You’re attracted to her because dating someone who can get away with calling your shittier dude friends “basic bitches” makes you seem infinitely more interesting. A brutal and unpredictable temper though. Probably not marriage material, but a nice few-month fever dream.
7. Rave Girl
Very similar to Sasha, except rave girl is much less show. I.e., whereas SRS may qualify every action with some sort of outward appearance end goal, Rave Girl doesn’t necessarily give a shit about what other people think.
Of course, this is a very attractive quality, particularly initially. But then you realize she doesn’t mess around when it comes to drugs, and her morals are highly questionable to say the least. Whereas SRS may pretend to have the balls to cheat on you, Rave Girl doesn’t even take a second to think on it. She’s successfully reversed the more traditional dating roles, because its now you who will stop at nothing in order to change her. You know there’s no reason it should take you years to get over her, but she’s very much got that devilish power.
*Note – attending raves is more about the characterization of this one–she espouses to a free-flowing, no fucks given lifestyle. She may hate electronic music with a burning passion.
8. NY Times Wedding Or Bust
She’s the quintessential hot girl that many Bro-types tend to disparage; partially because the stereotypes are spot on, but partially due to the deep seated frustration/jealously that comes with never being able to land one of these Real Princesses of Actual Society.
She’ll come from an intimidating background, she’s known how to pronounce things like sommelier since age 11, and she’s by no means a girl you “just hook up with.” She’s dating down to you because you offer something her overly regimented Top Flight Prep School → Brown → Social Activist Lawyer ambition binge success track largely ignores. You don’t really know what that is, but it’s a premise good enough for you to roll with.
Eventually, the expectations will get to you. And let’s face it, you’re ultimately not marriage material. At least not until your 30’s. 
