Crazy Ex-Girlfriend begins when successful but unsatisfied lawyer Rebecca Bunch turns down a promotion at her New York City firm and instead moves to West Covina, California (It’s two hours from the beach! Four in traffic.). Why? Well, her ex, Josh Chan from camp when they were 16 years old, lives there. What Rebecca’s really after though, is happiness. And Josh represents the last time Rebecca was actually… happy.
While Rebecca’s relationships with Josh and several others have only been part of Crazy Ex-Girlfriend‘s story, romance is certainly an important element of the series. A relationship can be a source of happiness — or it can be a dumpster fire of despair. And throughout the show, Rebecca and the other characters have experienced both extremes, sometimes with the same person.
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Here, we explore the best and worst couples on Crazy Ex-Girlfriend.
10 Worst: Heather And Old Greg
Heather and Greg initially met through Rebecca in season 1 and soon started dating. They shared a sardonic outlook on the world that gave them a cute chemistry. And Heather was willing to call Greg on some of his nonsense.
In other circumstances, maybe these two could’ve made it work. However, they make our worst list, because despite everything they had going for them, throughout their relationship Greg was in love with Rebecca, dooming their relationship from the start. Heather wanted to take things to the next level but when she realized the truth about Greg’s feelings, she quickly let him go.
9 Best: Rebecca And New Greg
In season 4, Greg comes back to West Covina after leaving to attend business school at Emory University (“the Harvard of the South!”). He’s also finally sober and looks like a completely different person. Yes, this is because in order to bring the character back, the show recast Santino Fontana, the actor who played Greg in seasons 1 and 2, with Skylar Astin, who is the season 4 version of Greg. But the recasting also speaks to how Greg has changed and how Rebecca’s perception of him has shifted in the years he’s been gone.
When Rebecca and New Greg got together they were both in a much healthier place. Unfortunately the relationship didn’t last because Rebecca wasn’t yet sticking with her therapy regime the way she needed to. For the brief time they dated though, they were a fairly functional couple.
8 Worst: Rebecca And Old Greg
Greg met Rebecca when she moved to West Covina in season 1. He immediately fell for her, even though it was clear that she was obsessed with his best friend Josh. He didn’t care if Rebecca was only settling for him, he wanted to be with her.
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Eventually, Rebecca gave Greg a chance, and even realized she had genuine feelings for him. His problems with alcohol and Rebecca’s continued preoccupation with Josh got in the way though. While Rebecca wanted to give it another chance, Greg decided it was best for him to leave town for business school, pointing out that their relationship had been a disaster from the start.
7 Best: Paula And Scott
When Crazy Ex-Girlfriend started, Paula and her husband Scott weren’t in a good place. Married with two sons, the realities of life had put them in a rut. So when Rebecca moved to town, Paula quickly got swept up in the drama of Rebecca’s quest to win Josh’s affections. This added the excitement to her life that Paula was missing but drove an even deeper wedge between her and Scott.
That is, until she had to enlist Scott’s help for a Rebecca-related quest. The thrill of it got them to start talking again. They bonded over Rebecca’s antics and finally reconnected. Soon, their relationship rebounded with Scott being supportive and helpful when Paula went back to school to get her law degree.
6 Worst: Rebecca And Josh
It’s no secret that Rebecca moved to West Covina for Josh Chan, and even though he had a girlfriend, Rebecca eventually managed to win him over. Josh was accepting and warm and Rebecca truly believed in him even if he wasn’t that ambitious. Soon they were engaged and Rebecca even found a dream location for the wedding.
Unfortunately, by that point the relationship couldn’t survive. Between Rebecca’s extensive manipulations, both partners overlooking their incompatibilities and relationship flaws, and each hiding their concerns instead of talking them through, the relationship was fatally flawed.
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Josh ended up abandoning Rebecca at the altar to become a priest — a terrible career fit for him, but a sign of how much he wanted to get out of the relationship.
5 Best: Valencia And Beth
Beth was originally a client of Valencia’s up and coming event-planning business. The two hit it off and Valencia realized she was bisexual. This led to a relationship that brought together both their personal and professional lives, with Beth becoming a partner in Valencia’s business.
The pair have a solid, low-key romance that works for both of them. They complement one another well, each having different skills and perspectives that help them grow their business and their relationship. The partnership has given Valencia a new, more mature perspective.
4 Worst: Valencia And Josh
When Rebecca first moved to West Covina to pursue Josh, it wasn’t long before she learned that Josh already had a girlfriend: Valencia. Josh and Valencia were high school sweethearts and they’d stayed together well into adulthood. Still, they weren’t yet engaged or living together when Rebecca rolled into town.
Ultimately, Josh and Valencia’s relationship became the high school romance that went on way too long. It was clear that the couple had grown apart and wanted very different things. Yet, neither was quite ready to let the other go until Rebecca entered the picture and started attracting Josh’s attention. Despite the way it happened, their break-up was the best thing for both of them.
3 Best: Heather And Hector
A spark was unexpectedly lit between Heather and Hector when Rebecca spiraled after Josh left her at the altar. At first they seemed like an unlikely couple. Hector still lived with his mom, who he claimed was his best friend, and habitually overslept and missed beach trips with his crew. And Heather was a recent community college grad who had stayed in school as long as possible to avoid having to figure out what to do with her life. Plus, his enthusiasm seemed to clash with her sarcastic detachment, but ultimately Hector’s patience and support was just what Heather needed, especially after she agreed to be a surrogate for Darryl’s baby.
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Eventually he moved in with her and soon she proposed they get married so he could use her health insurance. Hector wanted a big wedding but Heather was against the commodification of their relationship. Realizing she cared more about giving him what he wanted though than getting her way, Heather surprised Hector with a big ceremony in front of their friends and family.
2 Worst: Rebecca And Trent
In many ways Rebecca and Trent are two sides of the same questionable coin. While Rebecca was busy obsessing over Josh, Trent was obsessing over Rebecca. And just like Rebecca manipulated situations to bring her closer to Josh, Trent did the same — even going so far as providing information that led to Josh skipping out on his wedding to Rebecca.
In certain ways, Trent has proven himself far scarier though, especially when he blackmailed Rebecca into being his girlfriend. Trent was far more interested in his own happiness than Rebecca’s. However, when Rebecca finally openly rejected him, Trent tried another tact — going after her ex, Nathaniel, for revenge. To protect Nathaniel, Rebecca pushed Trent off a balcony, a move that led to a brief stint in jail.
1 Best: Darryl And White Josh
When Darryl was finally ready to date again after a messy divorce, he found himself attracted to White Josh to his surprise. After realizing this meant he was a “both-sexual” (or bisexual, as it’s more commonly known), the pair officially got together.
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Darryl and White Josh seemed practically perfect for each other. When they had issues and insecurities they talked it out, and WhiJo got along well with Darryl’s daughter. Darryl was even willing to accept WhiJo’s disinterest in getting married. They hit an impasse, though, when Darryl stated a desire to have more children and WhiJo wasn’t on the same page. Even though they still loved each other, they made the decision to split up so they could pursue what made them happy as individuals.