I feel like Squidward is the type of gay man who sexually imprinted on an unrequited crush in his teens and has been chasing it's shadow ever since. Sexually speaking I think it would be difficult for him to be present. It's not that he has trouble being vulnerable, I think he's a vulnerable if tense lover. Like whenever he sleeps with somebody new he can only see them when measured against an ideal he won't allow himself to fully comprehend. Because if he ever looks at it head on, he knows it will never happen perfectly. Like, he has a hard time indulging in his partners fantasies, especially when it clashes with the semiconscious image in his head. So the sex is pleasant but tense and distant.
It wasn't Squilliam. It was some other person that moved schools and vanished before the advent of social media. Squilliam was the NEXT uncomfortable crush, but it formed around the unresolved feelings from the first crush, which is part of why he's feels so bitter towards Squilliam.
