There’s a line in Carmy’s monologue about his life in the season finale that certain fans have clung to, where he mentions, “I didn’t have any girlfriends.” It’s a line that begs the question: didn’t, or haven’t? He follows it up with “I don’t think I’m funny,” a present-tense statement. By the sound of it, Carmy’s life has only gotten more chaotic since high school, so it would be believable if season 2 confirmed that he’s never been in a relationship before, especially not a serious one.
That makes sense, because the Carmy we meet in season 1 is definitely not in a good place for a relationship, and he himself seems perfectly aware of this. He spends most of his waking hours at work, and the rest of his time grieving his dead brother or arguing with his sister. Even his time at work isn’t exactly promising in this regard, because he constantly seems on the verge of a total mental breakdown.
“I really wanted Carmy throughout the season to feel really fragile,” Jeremy Allen White explained in an interview with Uproxx, “to feel like one wrong turn or somebody says the wrong thing and he could kind of pop.” It’s not a good mental state to be in for a relationship. When he screams at Sydney in episode 7, the show’s making it abundantly clear that these two have a long way to go before a romantic relationship would be anything other than weird and unhealthy. Carmy understands better than anyone that if he wants to get a girlfriend, he has to work on himself first.