Miles, Jack, Stephanie, and Maya - who wouldn't want to be friends with them?

They were the first ones I thought of when I saw this answer. Sideways is the ultimate buddy flick (in my mind). Although, I'd have to keep an eye on Jack since he's a player, but other than that, he seems like he'd be great fun to hang around with. He's the type of guy who's positive, upbeat, and laid back. He's also the spontaneous type, so you'd never be bored. He's also a great friend, and encourages Miles to look at the bright side of life, even though it's kind of in a way that gets them into sticky situations.

Miles would be great to talk to, mainly about wine, but also about movies, culture, intellectual stuff. He's the type of guy you can have long conversations with, but you'd never be bored either (*if* you're an intellectual yourself, otherwise, Miles isn't your guy). He can be morose and depressive, but I think it all stems from his divorce and the fact that he feels discouraged about being rejected and not getting his book published. But if you could get him out of his shell, he'd be a great friend to hang around with as well. He's very grounded, so you can depend on him.

Maya and Stephanie would also be fun to hang around with, especially Maya. She's Miles's equal, so she also knows a lot about wines and is also an intellectual, so she is an intelligent and strong person. She also seems level-headed and has both feet on the ground. She'd be a better friend than Stephanie, in my opinion, who's kind of wild and free-spirited, but the great thing about Steph is that she seems like a non-judgmental person, someone who isn't stuck up or snobbish. She'd be great to hang out with too.

Overall, I would be friends with all the characters in the movie because they seem like people you would know in real life. It's based in reality, which is what I love about this film. Character-driven, real-life stories have always been my favorites.