I'll make it easier for #3. He is not hugely famous but certainly famous enough that he's been discussed on this website. He made a splash in a big supporting role then got mixed reviews for his next role in which he played the lead. He was on the verge of stardom but had some problems with the law. I think he's retired from acting now.
And I'll add another one....a 20something very hot, gay singer/songwriter who was single at the time but broke up our FWB when he got into a relationship. Total bttm, and despite all of his 'save the world' leanings, and gentle persona, likes down and dirty unprotected sex.