I love Outlaw and Deadpools relationship. They care for each other in a friend way... one time friend's with benefits but yeah. I haven't seen Deadpool be sweet to anyone like he is Outlaw. I mean Siryn was definately the love of his life, but out of all his friends I think he love Outlaw the most. He almost never asks for help but he did from Outlaw and a hand full of other people including Copycat. 
 
Outlaw is even sweet with him when they're working for Agent X. LOOK AT THE LOVE AND TENDERNOUS IN HIS WHITE OUT EYES! Even behind the mask you can see there is definate emotion ties.

Bah, he needs to hook up with Typhoid Mary again.

she'll get killed, watch. I hope not though but do Deadpool characters ever not get killed?

I'd have to agree. I just finished re-reading this series and I think their relationship is really sweet.

Sorry to say it but...I'd love it more if he ended up with Domino.