Call it Blair Waldorf Syndrome: The case of the &#x C3;&#x BF;ber-perfectionist who’s head-over-heels in love with a classic cad like Chuck Bass.

Since the beginning of time, poets, philosophers, and psychologists have been puzzled as to why smart, savvy girls often end up swooning over the wrong guy.

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a good-looking senior who was somewhat of a rogue, asked her out.

"I was so overwhelmed by having to keep everything together all the time," Eleanor says.

"But if he’s getting into serious trouble, that’s when an intelligent girl should know to draw the line.""It doesn’t help," Carey points out, "that pop culture keeps us constantly infatuated with the notorious, not-so-nice guy." It’s true: With his trademark leather jacket and rebel-without-a-cause attitude, the bad boy has become a staple in the script of nearly every high school rom-com and TV series.

And the list of smart girl/bad boy duos has roots deeper than modern-day reference points like (Chronicle Books).

"Dating him felt like an accomplishment," she says.

Trevor was the ultimate test: He frequently blew her off, didn’t respond right away to her text-messages, and was completely unpredictable. I’m an overachiever and I like a good challenge," Ali admits.

"So I can see the need for a girl to want to be with someone who doesn’t require her to be perfect all the time." But the most important thing is to stay true to yourself, she explains, because ultimately you’re the one who suffers the consequences of breaking the rules.

Maddie, for example, was eventually able to see that by dating Brett, she was turning into someone she didn’t want to be.

"I know I eventually want to settle down with a good guy who’s ambitious," Ali says.

Evan liked to visit a local sports bar and relax with his old college buddies, which Cindy didn’t mind.

"Being with James was sort of my own form of rebellion.