Do you think you could see Spider-man, at the movies with Wade Wilson, or having coffee, and talking about TV shows? How long do you think their friendship would last, and why?

I think the could get along, but friends? hmmm totally different story there. 

Aren't they already friends?

"Aren't they already friends? "

Deadpool already thinks they're crime fighting partners but it seemed like Spider-man was more annoyed with him than anything

"Deadpool already thinks they're crime fighting partners but it seemed like Spider-man was more annoyed with him than anything "

@Primmaster64:
Nope, but I'm pretty sure Spidey and Deadpool aren't friends. The "Deadpool probably thinks they are" was a joke. 
 

 
Props for the reference to The Spectacular Spider-man. Love that show. Lots of homages to old comics in it.

I was originally just gonna mention the fact that Deadpool is a killer and Spidey doesn't generally befriend those types of people. 
 
Then I remembered that Spidey is kinda friends with Wolverine, lol 
 
But, to quote CATMANEXE (I think...) that is only because Marvel has turned both of these badass killers into "cuddly mascots" 
 
Marvel are seriously not so great with the rolemodels... Aside from Spidey, one of their biggest, most recognised characters is Wolverine, a character based on the idea of stabbing people. Now Deadpool, someone far worse than Logan, is following the same route... I love their characters, but I don't like the idea of making them rolemodels... Or producing toy Wolverine claws, so kids can pretend to stab each other, lol

hmmm

I don't see why not. Once Spider-Man stops acting all edgy around Deadpool then I think he'd find that they're alot alike. 
 
And really, Deadpool only takes assassination jobs when the people deserve it (like mobsters), and he rarely kills for free unless they are fellow "players," he's protecting someone, or they're total scumbags.