While Captain America is known for his relationship with Sharon Carter in the comics (and Peggy Carter in the Marvel Cinematic Universe), he has dated other people in the past as well - including Deadpool's current roommate, Blind Al. Steve Rogers' dating life isn't always brought to the forefront in the comics or the films; he's not one who would brag about this certain part of his life in great detail like Tony Stark, for example. Nonetheless, in Deadpool #25, written by Joe Kelly with art by Walter McDaniel and Walden Wong and colors by Matt Hicks, Captain America's past is revealed - along with quite a poignant lesson in a Deadpool comic, of all places.
Deadpool's unique brand of humor and overall general disposition can be best described as irreverent. His jokes are a mixture of pop cultural references, witty puns and crude and crass teenage humor. He laughs at his own pain as well as the pain of others - to a certain degree. But Deadpool is not without his moments of sincere grief. In this instance, Blind Al finds Deadpool despondent after a mission has gone wrong and a compatriot has died.
With Deadpool inconsolable, Blind Al tells a story of her past in World War II. She describes a soldier who was a 'real hero' who kept throwing himself on top of grenades. She takes out a gold medal and shows it to Deadpool. "This was his...he gave it to me in Moscow...the last time we saw one another. We were close." She asked 'Blondie' what it felt like to be a hero, to which the as-yet-unnamed soldier responded "I'm not a hero. I'm just a guy who tried to do the right thing...and didn't get shot in the process." Blind Al relates to Deadpool that since Wade attempted to be a hero, he failed - because a hero isn't something one can try to become.
When Deadpool admits that he is perhaps too afraid to act as a hero - a rare moment of vulnerability from the hero - Blind Al reveals that Captain America was not the stalwart hero he appeared to be. "When we were alone together...holding one another, trembling in the dark...it was all he ever talked about." Far from being a cheap joke, the writers of Deadpool took the opportunity to explore the characters of both Captain America and Deadpool, showing that neither is as simple as their outward image. At the end of the issue, Captain America manages to find the medal after a battle, on which he had written "To Althea - thank you for reminding me what it means to be a hero. Ever yours, Steve."
The Deadpool films never explored Blind Al's character in detail, but the comics show a layered human being with decades of experiences and memories from which to inspire others. Now that Deadpool is owned by Disney (and by extension, Marvel), perhaps the MCU debut of the character can allow for this level of poignancy. Captain America and Deadpool hide vulnerabilities behind their exteriors, and they are more alike that they would appear.