That would be really cool, the Marvel spy world is always full of such great characters and things going on. So, I would definitely like to think of some way they've crossed paths back in the day being all clandestine. Especially now that he's more freelance.
I'm completely good with Colleen and him meeting up either way, all things considered. Whether he's trying not to lose his not-bionic arm to her blade or happens to sit by her on a train, it'd be good times. Colleen is not around enough, so I'm stoked to write opposite her.
Kate and he have to meet when Clint is around so he can use a line similar to: "...Why do both of you have bows?"