- Pretty much anytime Spider-Man and Deadpool get along well and relate to each other, especially early on, as Spider-Man still despised Deadpool for being an assassin.
- In the tie-in Christmas special, Deadpool at one point asks Spider-Man if they're becoming best friends, which Spider-Man subtly agrees to. They give each other a Christmas present which turns out to be the same sweater featuring the two of them (except with swapped heads) that they later wear, with Spider-Man calling themselves "Bad besties for life."
- In issue 9, they have a heart to heart, while eating ice cream. Deadpool thanks Spider-Man for giving him a chance, even though he didn't deserve one. He says that even though Shiklah wants nothing to do with him, he's still never been happier and that Spider-Man is the reason. Spider-Man tells Deadpool that he really didn't do anything and that he just finally got things through his thick skull. He states that Deadpool is a good guy, and good guys stick together. Spider-Man is seen holding Wade's hand and they go off on his web together. This could be seen as Ho Yay.
- Spider-Man feels very sorry for Deadpool when he sees that his face is back to being burned, and hugs him, swearing that he'll make up for what Deadpool sacrificed for him. Of course, Deadpool can't help but ruin the mood, though he hugs back before doing so.
Heartwarming / Spider-Man/Deadpool