The Romances of Classic Deadpool
Copy-Cat/Vanessa:
Deadpool and Vanessa have an on-and-off-again relationship. She was Deadpool's girlfriend before the Weapon X program, but he broke up with her when he discovered he had cancer, as seen in a flashback. They start the Classic era broken up, but both working for the same man, Mr. Tolliver. By the first Deadpool mini-series, Deadpool expresses that he is still interested in her, but Vanessa has moved on.
Later, Vanessa enters back into Deadpool's life when she spends months pretending to be another mutant villain while she lives with Deadpool as part of an elaborate revenge plot she was hired for. She winds up taking all of his money and leaving him again.
She rejoins Weapon X, goes crazy, and gets involved with Deadpool again by pretending to be five different women who all want to hook-up with Deadpool. He knows it's her the entire time, and eventually confronts her about her scheme. They get together again, only to end for the last time when Sabretooth murders her.
Siryn.
One-sided on Deadpool's part. She seems interested in him when they first meet, but her interest disappears after she sees his face. She considers him a friend of sorts. Deadpool has her on a pedestal and depends on her to help him stay good and sane.
Death:
Deadpool meets death in a flashback issue centered on his time at Weapon X, where he was experimented on, tortured, and made insane. Unfortunately, his thirst for revenge triggered his healing factor at the end, parting him from Death.
He has a few more meetings with Death, first when he was dealing with Francis, a tormentor from his Weapon X days, later when he killed after a battle with T-Ray he got to spend some time with Death. When Death was captured by Loki, Deadpool had to play along with Loki's schemes against his brother Thor for a while in order to rescue Death, despite discovering Death's fickleness when Death preferred Thor to Deadpool. Finally, T-Ray had been hired by Thanos to try to strip all personality from Deadpool in the hopes of making Deadpool uninteresting to Death, since they were both in love with Death.
Typhoid Mary
Deadpool has no interest in Typhoid Mary until it seems like he’s helped her. That turns out not to be the case. And then she rapes him. He’s traumatized in the immediate aftermath, but decides to consider her somewhat a girlfriend. At the very least, he keeps a picture of her on his bedside next to the one of Siryn, and he considered going to her for help at one point when he was having trouble with the Loki curse. He ultimately didn’t, and she isn’t in the story much after the issue 14.
Anna
A tattoo-artist mob-girlfriend who sets Deadpool up as part of her plans to get away. She winds up falling for him, but her disregard for taking innocents out leaves Deadpool uninterested. He might have killed her.
Mercedes WilsonA woman that Deadpool thought had been his wife before he was Deadpool, but really she was a woman he had liked and killed in some weird story that makes no sense and I tend to ignore this plot line because T-Ray is stupid.
Sazae
I don’t count this one but for the sake of completion, I’m mentioning it here. According to a single issue side story, Deadpool almost married a Japanese woman named Sazae back in his mercenary days pre-Weapon X when he was living in Japan as a sumo wrestler.
Cable:
Deadpool has two big fights with Cable, both times Cable is able to defeat Deadpool (with help from Copy-Cat-as-Domino and the real Domino). There isn’t anything particularly special about these two fights. That is, to Cable, Deadpool is just another bad guy who fights him, but really, there isn’t much that would mark Deadpool as anything particularly note-worthy for Cable.
But Deadpool does seem to take notice of Cable. Well, okay, the first time Cable did bind, gag, and mail him, fed-ex, back to his boss, and Cable is probably among the few who have defeated Deadpool at this time. One of Deadpool’s image inducer forms has a glowy left-eye like Cable’s. He’s aware of Cable’s love life--he knows when Domino and Cable aren’t together anymore.
Then we get the one significant fight between the two of them. Deadpool has just learned that the great destiny he has, the one where he gets to be a hero and save the world, actually involves killing something, and Cable, who also has a destiny to save the world, is now powerless and dying before he can actually accomplish his life’s goal. The two fight and bond over the idea of being the unthanked garbage-men of destiny.
Some things of note about this fight. First, Deadpool has paid attention to Cable and knows that something’s wrong--he pretty much immediately realizes that Cable doesn’t have his powers. Deadpool also says several possibly-queer statements to Cable throughout their fight. These could be read non-sexually, or non-serious. Deadpool makes note of Cable’s “Charlton Heston voice”. Then he says, “We haven’t started yet and you’re winded? I hope you’d have the common decency to tell me if you’re suffering severe chest pains…it’d be a total tease if you dropped dead before I got a chance to smack the Pepsi out of you!”
Cable decides that the “Fights over. I’m prioritizing and you’re not that important to me right now.” And Deadpool agrees that maybe “I guess suddenly I don’t feel like tearing you a new orifice either” and they part ways.
Other than possibly seeing each other during the Contest of Champions II, they don’t have any further interaction until Deadpool’s funeral. Which might have been a dream/hallucination on Deadpool’s part, but taking the story at face value, Cable goes to Deadpool’s funeral, and he doesn’t go with Siryn, but on his own. There is nothing in their three interactions that would suggest that Cable thought enough of Deadpool that he would care about, or heck even know about a funeral for Deadpool.
Which is all to say that I am convinced that Rallamajoop’s story is completely and utterly true.
