How to Date Billy Walsh can be summed up in one word: cringe. This film is an excruciating watch on every level. The characters, particularly the background characters, are garishly over the top. The second-hand embarrassment will give you an ulcer; but worst of all, the main character has no redeeming qualities.
Our protagonist, Archie Arnold (Sebastian Croft), has been friends with Amelia ‘Milly’ Brown (Charithra Chandran) since they were infants, as he tells the camera in quite possibly the worst attempt at breaking the fourth wall to ever exist. He’s always loved her, but could never seem to find the words to tell her. He’s trying to work up the nerve to ask her to the end of the year dance when disaster strikes: a handsome new student from America, Billy Walsh (Tanner Buchanan), catches Milly’s eye, and she’s determined to win his heart. While Milly works to get Billy’s attention, Archie works to sabotage their relationship.
Despite claiming to love Milly, Archie’s actions are consistently selfish, with no thought of how they will hurt her – and when he does hurt her, he doesn’t seem to care. Early on in the film, Archie tells Milly that she should give up on her crush on Billy because, ‘Good looking people go for good looking people; not people like me, and not people like you.’ Milly runs away crying after essentially being told by her best friend that she isn’t pretty, but Archie doesn’t grasp how cruel this was. He doesn’t even apologize, instead texting her the next day, ‘Are you done not talking to me?’
In the first selfless act we get from Archie, he gets Milly to forgive him by giving her the contact information of a ‘love doctor’ that helped both Archie and Milly’s parents. This could have been a turning point for his character; but he doubles back on his decision, stealing the contact information and replacing it with the number of his second phone (why does he have a second phone? It’s a troubling question that remains unanswered). Archie uses age-altering AI to pretend to be the love doctor over video chat and gives Milly terrible advice to win Billy’s attention; like copying the most popular girl in school’s makeup look, which includes big drawn on eyebrows. This results in Milly being laughed at and humiliated; but that isn’t enough for Archie to stop. It’s painful to watch Milly follow the advice without question, particularly when she is advised to ‘act like everything and everyone is beneath her’ on her date with Billy. The amount of secondhand embarrassment this film puts viewers through should be considered a felony. Finally, she embarrasses herself enough that Archie grows a conscience and ‘ets her’ date Billy.
After a few bland dates with Billy, Milly eventually realises she has feelings for Archie and turns up in his room on the night of the dance to tell him. Since Archie can’t do anything without whining, he complains that they’ve barely spent any time together and tells her, ‘If you’ve had an argument with Billy and you want little old Archie to pat you on the back and tell you everything’s going to be okay, it’s not going to happen.’ For truly incomprehensible reasons, Milly doesn’t run and never look back, but instead tells Archie that she loves him.
To make matters even worse, Archie never comes clean to Milly about his deceit; he never even considers it. When he leaves the room for a moment, she finds his second phone, realizes he’s been lying to her and humiliating her for weeks, and storms out. In most films, a character would have weeks to process this information; but not this film! We head straight to the dance, where Milly breaks up with Billy and Archie gets up on stage to make a grand speech. It’s mostly an uninspired ramble about stars with a hollow apology thrown in, but because Milly lacks any independent thought, she immediately forgives him. They dance and kiss, and the audience is supposed to be cheering them on instead of yelling ‘No!’ or perhaps, ‘Why?’ at the screen.
At the start of the film Archie is selfish, entitled, and cruel. At the end of the film he’s selfish, entitled, and cruel, but with a girlfriend. We can only hope that someday, films will stop portraying men who are clearly going to end up starring in true crime documentaries as romantic leads. Until that day comes, we’ll just have to believe in our hearts that Milly will come to her senses and dump Archie in the most public and humiliating way possible.
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