Up In The Air (2009)

Clooney plays an older single guy. The character is a free loving type, not wanting to be tied down. He's a bit of a misanthrope, seeing people and relationships as a burden, and in a strange way perhaps enjoys his job of firing people, which he rationalizes as a way to free people for a 'better' life. In a turn much like (500) Days of Summer, he falls for a woman who acts much like a man in that she doesn't want or expect exclusivity, just one night stands. At points, Clooney's character extols on the virtues of being single, so much so that we're surprised when he starts to have doubts. At his sister's wedding, he's presented with indirect evidence of the major trade-off of marriage: companionship over loneliness and burden of responsibility for someone else's happiness over free wheeling independence.