Esteban Gonzalez’s review published on Letterboxd:
¨There can't be a happy ending. Because there has never been a happy ending for you.¨
Director Joe Swanberg teams up once again with Jake Johnson for this romantic drama where a gambling addict falls for a single mother and tries to mature along the way. Now stop me if you haven't heard this plot before where a man named Eddie (Johnson) plays an immature adult who is eager to make easy money, but has never had a real job. Along the way he falls in love with a dedicated nurse played by Aislinn Derbez (the daughter of Mexican actor Eugenio Derbez) and decides he wants to clean up his act. Eddie has an older brother, Ron (Joe Lo Truglio), who owns a lawn-mowing company and who is eager to have him work his way up for him. Eddie is determined to turn his life around, but there is just one problem. His gambling addiction has left him owing someone a lot of money.
Jake Johnson delivers a strong performance as Eddie. He's a likable guy who you sympathize with despite his gambling issues. His relationship with this new women he meets seems to have a positive effect on him. The chemistry between the couple is solid and the film avoids being cheesy thanks to some solid dialogue. The story also has an important subplot revolving around Eddie and his brother who is concerned about his addiction and immaturity, however their relationship did feel forced at times and a bit weird. The jokes don't always work. I did think that the story took the easy way out at the end which kind of undermines everything that Eddie was trying to change about himself. I was still entertained thanks to Johnson's performance, but the film never manages to break out of its comfort zone. Win it All is yet another forgettable Netflix movie, but at least it wasn't bad.