Considering that not all of the good citizens of Gilmore Girls' Stars Hollow are folksy—who would ever describe Emily and Richard Gilmore or the Huntzbergers that way?—and not all the New York City socialites of Gossip Girl reside on Park, Madison, or Fifth Avenues, such as The Humphreys of The BK.
There's a pretty good chance that some stellar couples would emerge from a crossover between these two series, but, no matter how you cut it, there are those who definitely wouldn't last more than a few weeks and would drive audiences up the wall.
Wouldn't: Dean and Jenny
At first blush, Dean, who's originally from Chicago, would have had the city street smarts plus the small-town goodness garnered from living in Stars Hollow. This would mirror Jenny's city smarts but outer-borough humbleness. But, alas, there's too much stuff going on with Little J.
Where Dean embraced small-town life, working at the market, and high school sports, Jenny wanted to be Blair. She coveted the uptown world of designer clothes and society galas, the headbanded-world of those who hang on the steps of The Met.
Would: Jess and Jenny
We're talkin' Jess when he first arrived in Stars Hollow--restless, rebellious, and resentful that his father was gone and his mother couldn't handle him so she had to ship him off to live with his uncle Luke. (This is all before Rory's good-girl influence brought out his sensitive, literary type.)
Because leather-moto-ed minds think alike, he and Jenny would ride off into the rock-n-roll sunset on a Harley if they met after she was over the whole Upper East Side Blair-wannabe phase and started dressing like Debbie Harry during the Blondie years.
Wouldn't: Logan and Blair
Although it seems logical that these two heirs-apparent—he to the Huntzberger newspaper conglomerate, and she to the Waldorf Design fashion empire—would be drawn to each other like a preppy to a Ralph Lauren sweater, but Logan and Blair would actually be a match made in arrogance hell.
Both may be young, rich, and dressed for success, but each has a my-way-or-the-highway attitude, has to call the shots in every situation, and all their conversations would end up being a condescension-a-thon. No amount of inheritance could make these two get along.
Would: Paris and Nate
That's right. Competitive, bossy, biting, over-achieving Paris and the womanizing, UES golden boy. Here's why: Nate Archibald is a Vanderbilt on his mother's side with grandfather William calling the shots for his future. Just like his politician cousin Tripp who faked heroism and had an affair with Serena, Nate sowed his wild oats all over Manhattan and the Hamptons in high school and college—and a bit beyond. However, as an adult member of the society family, he's got to present as respectable.
Enter Paris. Who better than this Yale-educated, super accomplished, and totally driven woman? She would treat being a scion's wife as though it were a CEO position at a Fortune 500. President of the Junior League? Park Avenue doyenne-in-training? Bring the limo around, Paris has places to go and minions to bark orders at.
Wouldn't: Serena and Logan
No, not these two either. Blonde and good-looking could guarantee that their kids would be gorgeous, but they'd never get close enough to find out.
The thing about Rory was she made Logan look like a rebel. He'd play the bad boy (FYI: it wasn't hard to look like a bad boy next to the Gilmore good girl), and Rory would beg him not to go, let's say, hang gliding, then stand on the sidelines clutching her pearls. Whereas Serena really was a rebel; a fierce individual, try-anything-once girl who'd call Logan's daredevil bluff and show him up as a poseur.
Would: Luke and Vanessa
Unlike Lorelai, who monopolizes every conversation, came from money, and always seems to have a new guy to dump Luke for, Vanessa is down-to-earth and authentic—hence her desired profession as a documentary filmmaker—and she never let the materialism bug bite her, no matter how much time she spent on the Upper East Side.
For her, Luke would represent the guy Dan once was, before he ed the Constance Billard/St. Judes crew and started participating in how-the-other-half-lives events. Residing over the diner in a peaceful town and living a simple life, leaving only to shoot a doc then go to Sundance to premiere it, accompanied by her ive guy, Luke's lifestyle would suit Vanessa just fine.
Wouldn't: Lane and Dan
This seemed to have potential; Lane had a Vanessa vibe—creative, salt-of-the-earth, and unpretentious. Yet, there's a little girl quality about the drummer and audiophile, no doubt thanks to the oppressive Mrs. Kim, who wanted to keep Lane home with her bible instead of participating in activities with kids her age.
Dan may not be the most sophisticated guy, but the girls he's been hanging with since high school sure are and present older and more worldly than Lane, even after the latter was married. Even though Dan is a creative soul like her, Lane really only wanted relationships with musicians who shared her ion.
Would: Dan and Rory
Now we're talking. Oh, what they have in common! Let us count the ways. Both Dan and Rory were outsiders in uniform; he at St. Judes where he had to take a train and a bus from Brooklyn to be bullied by Chuck and Blair, her at Chilton, where she was bullied by Paris and Tristan, who used to call her "Mary."
The easy-going, good-natured pair are also both writers. We can see them living in a loft with "partner desks," where she would be writing her earnest newspaper, magazine, or website articles, while he toiled away at another novel?
Wouldn't: Chuck and Rory
This coupling would be downright frightening. Imagine them being introduced by Emily and Richard after Rory's grandfather underwrites an insurance policy for Bart's Bass Industries. Along with Chuck's dad, they would see it as a melding of two powerful families.
Envision Chuck in all his swaggering glory rolling his eyes as he meets the pure-as-the-driven-snow junior Gilmore, who once went to visit Jess in NYC for a few hours, and it was panicked over as though she'd run off and ed a cult. We all know what Chuck is like when he gets angry and smart-alecky. If he tried to sexually assault Jenny for the "fun" of taking someone's innocence, imagine what he'd try with Rory. After a minute in his company, she'd make a run for it.
Would: Rufus and Lorelai
Are they not the cutest? He's plaid-shirted Luke, but with a personality, and she's, well, not Lily and her UES pretentiousness—or his ex-wife who cheated... or Ivy, who was an imposter.
Both Rufus and Lorelai suffer from a Peter Pan complex. He longs for his youth when he fronted Lincoln Hawk, and she longs for a youth cut short by a high school pregnancy. They both own their own businesses; he an art gallery, she an inn. They're both only parents who set their kids to private schools they couldn't afford, so the students had a better chance at getting into the Ivies. Both have children who are writers. Each knows how to navigate high society but want no part of it. This is a profile pairing made in Match.com heaven.