The wacky narratives of Brooklyn Nine-Nine owe a lot to the sitcom revolution brought about by Seinfeld (which ended about 16 years before Brooklyn even began.) The 99 is packed with a diverse array of characters — solemn Holt, playful Jake, obsessive Amy, narcissistic Gina, no-nonsense Rosa, generous Charles, and paternal Terry. Each of them is different in a way that makes their backstories and lives completely believable.
On the other hand, Seinfeld doesn’t follow any semblance of a plot, instead consisting of discrete accounts of real-life situations, as revealed through the comic genius of Jerry Seinfeld and Larry David. In this regard, its characters, though detailed, are just vehicles for the series’ take on the post-modern human experience. So how would a cross-show romantic pairing work with these two cases?
10 Would Work: Jerry & Amy
This relationship might start off rocky, as both Jerry and Amy are eerily similar to each other in terms of their need for perfect organization and maintenance of control over their lives.
However, given enough time, it would likely mellow into a warm romance, as Amy clearly loves funny guys, and Jerry has a thing for strong women who don’t cut him any slack. Of course, he usually runs away from these women, but Amy has the willpower necessary to make him understand the pros of dating her far outweigh the cons.
9 Wouldn’t Work: Kramer & Rosa
Rosa’s uber-strong personality will sit perfectly well with Kramer, whose penchant for distant, unavailable women has been well-documented. In fact, he is allegedly able to “convert” Susan’s girlfriend without much effort (although this is way too much of a stretch to be realistic).
Unfortunately, Rosa does not appreciate partners without any sense of direction in their lives, considering how carefully she has measured and planned out her own. Besides, Kramer’s intrusiveness will put her off completely.
8 Would Work: Newman & Gina
Weird as it might sound, Gina appreciates quirky men who don’t care what anyone thinks of them, those who are certain in their convictions, ridiculous and exaggerated though they be.
Further, Newman has proven that he is able to date attractive, engaging women (Jerry is so shocked that his neighbor dumped his girlfriend in the past for not being his type that he breaks up with her). This cavalier attitude towards dating is not shared by any other character except Kramer, and Gina is liable to find his casual disinterest most alluring.
7 Wouldn’t Work: Elaine & Charles
Charles Boyle is a sweet, generous man who only has nice things to say about everyone. Nevertheless, Elaine, while she does try to be a good person, often lapses into her own preconceptions of how the world should be, not to mention the number of times she has dated men who defy her s0-called principles (or broken up with them for the shallowest of reasons).
More importantly, she doesn’t care for sensitive men, as observed through the snide remarks she makes when Jerry does anything even mildly emotional.
6 Would Work: Charles & Susan
On the other hand, Susan would make an excellent partner for Charles, and vice-versa. They are both open, warm, and able to handle extremely harsh partners (George and Eleanor, respectively).
It’s essential that these two characters receive someone to build each other up, rather than have to do all the emotional labor in the relationship. More importantly, Susan is a romantic at heart, which George is not capable of fulfilling, but Charles is another matter when it comes to displays of affection.
5 Wouldn’t Work: Rosa & Jerry
Jerry’s OCD tends to be towards the excessive, like when he has to empty out his whole bathroom due to the paranoia of not knowing which object had been dunked in toilet water.
Rosa lives a spartan life (well, at least from the 99’s viewpoint, granted that they know next to nothing about her), so his wheedling and whinging is certain to be a pain in her neck. Also, Jerry will definitely find way too many “faults” with Rosa — she doesn’t smile, she wears only black, she rides a motorcycle, the list is endless.
4 Would Work: Susan & Rosa
Aside from the fact that both characters come out as bisexual in the middle of their respective series, Susan and Rosa are equally hardworking people, but neither of them would put their jobs before their partners.
One of them loses her position as an NBC executive, but continues dating George even though he gets her fired, while the other breaks out of her comfort zone and kisses her girlfriend in full view of the entire station. This shows that Susan and Rosa are willing to iron out any differences that might be hindering their prospective relationship.
3 Wouldn’t Work: George & Gina
There is no way that Gina would go for an obsessive, manic, self-flagellating man like George Costanza. He regularly puts himself down, claiming that women don’t want bald, unemployed men “who live with their parents.”
To Gina, these words are supremely defeatist; to be clear, her stint with Charles has nothing to do with the latter’s submissive nature, because George is anything but submissive. He’s not shy, he’s terrified of looking bad in front of someone he likes. It could theoretically work, but only if he does “the opposite” of what he normally does.
2 Would Work: Jake & Elaine
Elaine’s interest in men is varied, but it usually boils down to two things: attractiveness and adventurousness, features that Jake has no lack of whatsoever. He might be initially displeased by her intrinsic habit for dissing everything she sees, but in the end, he would find her zest for life adorable.
Elaine is cheery, intellectual (to a point, just like Jake), and intrepid, ensuring that they are probably going to enjoy each other’s company at the very least.
1 Wouldn’t Work: Amy & Kramer
Amy will take one look at Kramer’s life (or, if she has no time to analyze everything, his apartment), and instantly write him off as a potential romantic partner.
To be fair, though, it’s not like Jake has everything under control, but at least he’s willing to try, to change, to become better for the people he cares about. Kramer, however, will always remain Kramer, leaving scant possibility for anything serious to develop between him and Amy.
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