It seems that the wild side of Watchmen's Nite Owl is rooted in the hero's heartbreaking past. The prequel series Before Watchmen: Nite Owl reveals Dan Dreiberg's most kinky self has a small connection to his brief fling with the vice queen, Twilight Lady.
Watchmen is a superhero deconstruction story that posits the idea of superheroes existing in the real-world and history being shaped by their presence. The story largely revolves around the retired heroes from the second wave of costumed crime-fighters, one of which is Dan Dreiberg, the second Nite Owl. During the story, Dan becomes romantically involved with the Silk Spectre, a fellow second generation superhero and former teammate. After an awkward attempt at hooking up, Nite Owl and Silk Spectre venture out to save a group of residents from a burning tenement. The success of the mission ends with the heroes having an amorous affair in Nite Owl's airship.
However, it seems that Nite Owl's proclivity for mixing superhero business and pleasure was something that existed years before his exciting romp with Silk Spectre. In Before Watchmen: Nite Owl by J. Michael Straczynski and Andy Kubert, Dan becomes enamored with the Twilight Lady, a woman who provides New York City with pleasures unfit for more conservative crowds. Despite the words of the previous Nite Owl, Hollis Mason, and Dan's partner, Rorschach, Dreiberg begins seeing Twilight Lady as he begins to look into a case involving the murders of sex workers in New York. Twilight Lady helps Dan become much more unencumbered and encourages him to explore a more daring side of himself. The two even engage in a couple of spicy flings, though Twilight Lady draws the line at Dan's insistence that he remain masked during their dalliance.
How Nite Owl's Past Love Affected His Future
There isn’t much seen of Dan's ex in the original Watchmen story. When Silk Spectre stumbles upon a picture of Twilight Lady in Dan’s study, he implies that she was a villain that was fixated on Nite Owl. But the truth is that Dan was the one that was taken with Twilight Lady as she showed him that the costumed life he was leading could be a source of thrills. Unfortunately, Twilight Lady breaks Dan's heart and moves on, but the passion Dreiberg associated with his costumed life remained long after their time together.
The love scene between Silk Spectre and Nite Owl is meant to highlight what drives Dan as a superhero in Watchmen. It’s clear that Nite Owl gets a serious level of excitement from his life as a costumed hero. However, that kick takes on a whole new meaning once his past with Twilight Lady comes to light. She released something in Dan, a more uninhibited side of the nebbish figure. Twilight Lady helped Dan discover what really motivated him as a hero. Unfortunately, his passionate time with the villain left a hole in his heart, one he kept trying to fill with similar escapades. Nite Owl’s costumed kink might just be one of the most heartbreaking backstories in Watchmen's mythos.