A lot of unbelievable things happen in 13 Reasons Why — I mean, this is a show with ghosts, murder mysteries, and heavily tattooed teenagers, after all — but in the show's final season, it was the romances that left fans scratching their heads. In particular, the newly pivotal character Winston seemed to fall in love unreasonably quickly. However, actor Deaken Bluman's quotes about Winston and Monty on 13 Reasons Why help make sense of their whirlwind romance.
Spoiler alert: This post contains spoilers from throughout 13 Reasons Why Season 4. Winston only briefly appeared in Season 3, but he was promoted to a major role in the show's final season. Prior to Monty's death in the Season 3 finale, Winston met Monty at a party and hooked up with him, only for the sexually repressed jock to then brutally beat him up. That didn't end their relationship, though, as Monty went back to Winston's house and slept with him on the night of Bryce's murder.
As the only person besides Clay and Ani who knew of Monty's alibi, Winston became a major threat to the Liberty High kids who framed Monty for Bryce's murder, and he spent all of Season 4 trying to uncover the truth. But for many fans, his motivations seemed a bit... much. The final season provided no further exploration of Winston and Monty's relationship aside from a short, ghostly prom dance, so it felt unrealistic to viewers that Winston would be fighting so hard and professing his love for a guy he seemingly only hooked up with a couple times.
Bluman agreed Winston and Monty's love story would have made a lot more sense if Season 4 included some flashbacks of them together. To prepare for his more emotional scenes, Bluman told TVLine he imagined moments that deepened Winston and Monty's relationship beyond the two hookups viewers saw: "In developing that relationship, I was always referring to flashbacks that the show never had. Like, them jumping in the car and going to Palm Springs for the weekend, listening to great music and getting to know each other and really falling in love. People didn’t get to see that, but hopefully they felt that. It wasn’t just a one-night stand. They had a lot of love and a lot of fun together."
While some romantic flashbacks definitely would have helped better justify Winston's motivations, it did feel like whirlwind love stories were emblematic of the final season. Winston also fell incredibly fast for Alex, and then Alex moved on to Charlie right after ending things with Winston. At least now fans know Winston really did have something special with Monty that lasted more than a couple hookups — at least in Bluman's mind.