I'm torn on who 'dimples' might be. But for the darker one - I would hazard
James Franco? He fits in pretty much every way, but I'm not sure Lainey would say she finds him super gross. If not James Franco, I would also guess Alex Pettyfer - because he's so difficult, but he's not really acclaimed, nor does he front to be dark.
I'm trying to think of an actor who might be considered 'acclaimed' but also super cute...which is actually quite tough
It has to be someone who is single at the moment or in a new relationship hence the 'trying to go back to the other side of his bisexuality...' I thought it might be Zac Efron, but again, he's not 'acclaimed'
I keep editing this as I get more ideas
Here's a random guess if it's not James Franco...what about Joaquin Phoenix for the dark one?!