Michael Cordero: Jane The Virgin
Michael had a rough road to winning Jane's heart in Jane the Virgin. Jane had a long-term interest in both Michael and Rafael, which sparked an intense rivalry between the two, as Michael did all he could to protect Jane. After finally securing her love, Michael and Jane get married, but, in the true nature of a telenovela, Michael dies of a heart attack a short time later. As it turns out, the evil mastermind Sin Rostro faked his death and wiped his memories, and after four years pass, Michael is reunited with Jane, but he doesn't have his memories.
Michael Returns In Jane The Virgin
The rollercoaster relationship ends with Michael finally regaining his memories, but Jane chooses Rafael anyway. Michael ends up engaged to a new girl, but it doesn't change the fact that, after so many years and shed tears, he and Jane part ways, because Sin Rostro took four years of his life and all of his previous memories from him. Michael deserved to have his happy ending earlier, with his family, instead of being targeted and violated in so many ways.
Glenn Rhee: The Walking Dead
Glenn is one of the absolute best characters to appear in The Walking Dead. From his first appearance in episode 1, when he helps Rick get out of a tight spot, until his brutal demise in season 7, episode 1, Glenn was always looking out for the group. Glenn finally found someone to make a life with, Maggie, and they were blessed to fall pregnant and bring in a new generation to carry the world past the apocalypse. However, despite evading death on several occasions, he was brutally murdered to make a point by Negan.
Steven Yeun as Glenn in The Walking Dead season 7.
Andy Bernard: The Office
Andy undergoes a huge transition from his debut in The Office in season 3 through the following seasons. He goes from being a smug and insecure man to someone considerate and thoughtful while dating Angela. However, when he learns that Angela and Dwight are having an affair, he struggles to bounce back. He then pines over Erin for some time before they briefly date, but his role in the later seasons of the show sees him descend into becoming a caricature of himself.
Michael, Andy and Jim at Benihana on The Office
Andy becomes the manager at the Scranton branch, but he spends all of his time and energy chasing a career as a performer, musician, and actor. He behaves erratically and does many things which result in him becoming the butt of many jokes around the office. The series finale gives him a redemption arc with a job at Cornell and significant popularity following the release of the documentary that was filmed over the course of the show. Andy's reconciliation is sweet, but it was a difficult journey to get there thanks to Andy's weird arc bringing him to extreme lows.