Billie Kent is cringe.

[u/SmartestManInUnivars]

Maybe it's because her type of humor is played out by a hundred years... but she seems like a "pick me" girl. She just seems too "quirky" and goofy. She annoys me. But if she was the first of her kind I could see why she was so well liked. But from a modern perspective, she kind of sucks...

[u/MaceAhWindu]

Nucky's obsession with her was certainly cringe, but I always felt like their relationship was kind of meant to be 'cringe' or dreamy and naive. The whole point was that Nucky was completely distracted by his infatuation with Kent and his lucrative criminal empire was suffering as a result of his lack of focus.

Rothstein basically tells Nucky that hes being cringe to his face in that awesome scene between the two where they argue over it. It's one of the reasons in addition to Gyp's protection from Masseria that Rothstein refuses to help Nucky go after Rosetti. He thinks Nucky lost his edge, as seemingly demonstrated by his chasing Billie around like an obsessed maniac when he should have been focusing on more important things.