10 Major Relationships, Ranked Least To Most Successful


Ah, relationships. That everlasting bond between certain people extends past the ordinary world and into the realm of TV and film as well. Everyone wants to see a certain relationship succeed, like the quirky yet heavy-hitting ones on the hit comedy series, Brooklyn Nine-Nine.

RELATED: Brooklyn Nine-Nine: Every Holiday Episode, Ranked Worst To Best

On a comedy show like this, one wouldn’t expect relationships to be a big deal. However, as the show enters its eighth season, it boasts a range of complex relationships over the series one hundred and forty-five episodes. Each relationship has therefore led to key characters developing further and making the show much more than just a typical comedy series.

10 Charles And Gina

Charles and Gina looking upset

This is one relationship that’s just bizarre to think of. For one, the relationship between Charles and Gina never really felt right. It felt as if they were pushed together in an attempt to spice things up but things never really went anywhere.

Things got even weirder when their parents got married, which made them step-siblings. It’s just one of many Boyle and Lenitti relationships that have gone sour within the 99th precinct.

9 Charles And Eleanor

Eleanor harassing Charles

Speaking of Boyle, there’s another relationship that just didn’t work out for Charles: Eleanor. For most of the show, Eleanor is left out and only spoken of in… strange context, with Charles sometimes calling her mommy.

Yet, when audiences meet Eleanor in season three, it’s obvious from the start that she’s a manipulative woman who uses Charles for her own benefit. One could tell how toxic the relationship became, especially when she blackmailed Charles into clearing her charge. Thankfully, Charles managed to cut all ties with her and is now happy with his family.

8 Amy And Teddy

Amy meeting Teddy

Right off the bat, Amy and Teddy seemed like they had been good for one another. However, as time wore on, it’s obvious that Amy and Teddy’s relationship didn’t work on so many levels.

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From Teddy being the blandest person alive and Amy’s Type A personality, they were just too similar to one another. Still, it’s a wonder they fell for each other considering Teddy crossed a personal boundary several times.

7 Jake And Sophia

Jake spending time with Sophia

Side note: if one ever gets into the profession of being a cop, never date a defense lawyer. It just won’t work. On the surface, Jake Peralta and Sophia Perez’s relationship could’ve worked out. Both were fans of Die Hard, and Sophia shared some of Jake’s same traits and strange tastes in food.

When it came down to it though, Sophia was much more focused on her job than she was on Jake. It was the reason why she broke off their relationship in the first place, which Jake did not take well.

6 Rosa And Pimento

Pimento wanting Rosa back

Just because two characters have the same type of reputation, doesn’t mean that they’re always the best for one another. Rosa Diaz and Adrian Pimento (who had some great episodes in the series) are one such pair, with one being a hardened cop and the other being a somewhat disturbed undercover cop.

Where the relationship falters is that Adrian and Rosa weren’t really the best for one another. While they had the same traits and personalities, they couldn’t necessarily balance each other out in the right possible way and allow each other to grow as people.

5 Rosa And Jocelyn

Rosa and Jocelyn together

After going through the turmoil of the Adrian Pimento relationship, Rosa struggled through several more before coming across her latest partner, Jocelyn. Despite having broken up in season seven, the fans did like the influence Jocelyn had on Rosa.

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When they were dating, Rosa was seen to be a lot more open and caring. There was even a point where Rosa decided to put more focus on their relationship instead of working. Unfortunately, Jocelyn just couldn’t cope with Rosa’s hectic work schedule and decided to call off the relationship. It would have worked otherwise.

4 Charles And Genevieve

Charles greets Genevieve in prison

Despite his bad streak of luck with several girlfriends, Charles does end up succeeding in one relationship with Genevieve. Meeting her while attending court, Charles and the jailbird fell in love.

Not only are the pair happy but they’ve also adopted a child from another country, Nikolaj. Of course, that led to them trying to adopt Nikolaj’s “brother,” which ended up being a scam. Yet, the pair’s strong connection has helped them overcome the odds.

3 Terry And Sharon

Terry and Sharon celebrate their new baby

Look, not every relationship is going to be perfect. However, there are often times where the audiences find themselves relating to them. A prime example being Terry Jeffords and his wife Sharon.

Not only has Terry proved himself to be a truly amazing dad but he has had a fantastic relationship with Sharon. Although it’s been a little rocky in some spots, they are always willing to discuss these through and come together for the sake of their kids.

2 Jake And Amy

Jake and Amy welcome Mac into the world

Now, this is one relationship most people would expect to be the OTP and while it’s not, it’s still one of the more successful relationships in the series. Everyone saw the attraction between the serious Amy and lighthearted Jake. However, no one ever thought they see it go past the boyfriend and girlfriend stage.

RELATED: Brooklyn Nine-Nine: Every Season Finale, Ranked By IMDb

As the Nine-Nine enters its eighth season, Jake and Amy are married and now have a baby boy, Mac. In truth, the pair ended up being the definition of relationship goals with some truly big episodes moving the couple forward.

1 Holt And Kevin

Holt and Kevin at dinner

Ever hear of the term “chef’s kiss”? Chef’s kiss is a term used to describe something that is just perfect, the cream of the crop, the best it can be. For Brooklyn Nine-Nine fans, many believe that Jake and Amy are the chef’s kiss.

The reality is, the most successful relationship on the show belongs to Captain Holt, who’s given the show some of its best quotes, and his husband, Kevin. Both balance their lives perfectly, get along fabulously with one another, and are willing to put themselves at risk to save the other. Considering they have been together for more than 30 years, they are by far the strongest relationship on the show..

NEXT: Brooklyn Nine-Nine: Holt’s 10 Best Insults About Madeline Wuntch

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Updated: December 7, 2020 — 1:00 am

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