Marvel's Spider-Man is well-known for his inability to maintain a steady relationship, especially while acting as a superhero in New York. But his comic history has confirmed that his awful luck in the dating scene isn't just a Marvel fact, but true even in the DC Universe, too.
Peter Parker's street-level hero status doesn't stop him from traveling through other dimensions, timelines and planes of existence. The epic crossover Marvel vs. DC proves Peter can even ask out people from another company's reality entirely - but he never counted on having to deal with Superman in the process. In the 90s, both Marvel and DC Comics decided to increase sales through franchise-altering "events." Marvel's Infinity Gauntlet, DC's Bloodlines, and various other comic crossovers sold quite well, and both companies decided to cooperate - a nigh-impossibility in the modern age - to create 1996's Marvel vs DC massive crossover that saw the heroes of both universes battle one another for survival. Even civilians from both universes mingle, as Perry White and J. Jonah Jameson fight over the Daily Bugle/Daily Planet and Peter Parker is hired as the new photographer.
Peter Parker (who is actually Peter's clone Ben Reilly thanks to the Clone Saga, but goes by Peter in this comic) rescues Lois Lane from Marvel and DC's Scarecrows after a run-in with the pain in an alley. After the rescue, Peter wonders if Lois might be interested in a date after work. "I thought a nice normal date would be a little sanity in the midst of all this crazy stuff going on," he says to her. Lois is flattered, but she reveals she's already engaged. "To me." says Clark, who suddenly appears right behind Peter.
Peter is shocked and naturally horrified that he attempted to ask out the fiancée of Clark Kent, and though Kent doesn't appear to be insulted or angry, Peter's first instinct is to flee the scene as quickly as possible. Note that while Peter was technically married to Mary Jane at the time, this is Ben Reilly, so he's completely free to ask out - and be rejected by - women. Considering the fact that the two have more or less the same personality, this is a functional representation of Peter Parker asking Lois Lane out on a date and realizing that she will soon be married to Superman.
DC Comics in the 90s had a habit of drawing Clark Kent as a musclebound bodybuilder and not a mild-mannered reporter who blends into the background. Thus, Peter has every reason to be afraid of him. Spider-Man's relationships and romances rarely work out without occasional trials and tribulations, but in this instance, it was over before it began, thanks to Superman.