Since Gilmore Girls focused on a mom and daughter, two women who were beautiful, smart, fun and kind, there were a good amount of relationships featured through the years. And since Gossip Girl focused on an attractive and affluent group on the Upper East Side of Manhattan, there were always breakups, hookups, fights, kisses and even a couple of weddings.
What if these two worlds collided, though? How would things turn out, if all of these characters knew each other? And who would date? Here are six couples from these shows that would work and four that would be a disaster!
First up, it is easy to imagine Lorelai Gilmore and Rufus Humphrey together. This dad was into board games, making waffles and truly being there for his kiddos, while Lorelai enjoyed movie nights, junk food and being best friends with her daughter.
From how they spent their evenings and how they raised their children to the fact that he could feed her (a major plus on her end)... There are so many ways this could fit and work out!
Their significant others, however, would not work well together; Luke Danes was a simple man, while Lily van der Woodsen had certain expectations in life. Furthermore, she did whatever it took to stay on top, including some sneaky and devious things.
Luke needed someone who would live in Stars Hollow with him, who would be okay with his fishing trips and who had as warm and loving of a soul as he did.
Rory Gilmore and Dan Humphrey were both studious and intellectual characters with a passion for reading. They came from close-knit families and were good, genuine human beings. So this could have been a great match, as well!
Of course, if Lorelai and Rufus were together, this would put Dan back in a familiar situation, as Rory could become his step-sister. Guess he was meant to be with Serena van der Woodsen after all.
Speaking of S… She may have just ended up dating Dean Forester. Like Nate Archibald, he was an athletic and popular guy, with a laid-back and fun-loving personality. Separately, Serena and Dean would have turned heads, but together, they would have been a real power couple.
And, as proven by Serena’s relationship with Dan, having a nice boyfriend helps her be her best self, too.
On Gilmore Girls, Rory’s best friend from home was Lane Kim. As fans know, Lane was raised in a strict and religious household, but she was secretly into fast food and rock and roll. So while she did have a rebellious side, it is hard to picture her with Chuck Bass.
It would have taken a special person to truly love him and to help him love himself (as Blair Waldorf did), and he would have been super bored in Stars Hollow.
Two characters who also had wild sides were Jess Mariano and Jenny Humphrey. In their early years, they both made some poor decisions, with their too-cool-for-school attitudes. Deep down, though, they were good people, and they would have had a lot of fun together.
They would have also looked good together, with their black leather jackets and Jenny’s blonde hair floating in the wind, as they rode Jess’ bike!
At the end of Gossip Girl, Georgina Sparks seemed to be with Jack Bass, who was at least a couple of years older than her. So what if she went for another handsome and older man… like Christopher Hayden?
While she may have got his eye, Chris needed stability in life; one of the reasons things never worked out for him and Lorelai was because of his immaturity, and being with someone like Georgina would not have been the smartest move for him!
Logan Huntzberger and Blair Waldorf both came from influential families, and they were used to the finer things in life. Furthermore, neither of them were angels, so fans may be able to picture them scheming in New York and/or off on adventures with the Life and Death Brigade.
Blair could be a bit of a diva, and while Logan didn’t enjoy everything that came with being a Huntzberger, he would have gotten pleasure out of spoiling her.
A final pair that surely couldn’t work out would be the most uptight character, Paris Geller, and the most relaxed one, Nate.
She lived by lists and overachieving, while he was fine with spending all of his time with pretty ladies, playing video games and drinking. This would have ended in a not-very-pretty way.
Finally, there was Emily Gilmore, who was a supportive woman yet who could be so spiteful and bossy. Part of this came from her lifestyle, since she had the best and expected the best all the time from everyone.
Someone else with power and money and a mean personality was Bart Bass. And though Emily may not have approved of all of his methods, one can imagine him going about his business and Emily running the household and planning the events, as she did.
