As a grim, obsessed loner dedicated to fighting crime in all its forms, Batman is supposed to have no time for love, yet somehow nearly all his live-action movies have had a token love interest. However, the animated Mask of the Phantasm revolves around the idea that Bruce Wayne had a fleeting yet meaningful chance at romantic happiness when he was at his most vulnerable—and its loss is what finally sent him down on his tragic path.

Batman: Mask of the Phantasm manages a feat that very few comics storylines (and no other film adaptation) has accomplished: it makes you believe that Batman is—or was—capable of desiring a romantic relationship. The 1993 movie, recently released on Blu-ray, combines elements from several influential comics stories, like Batman: Year One and Batman: Year Three. It’s the closest that the Batman: The Animated Series team ever got to showing the main character’s origin—and the best Batman love story ever told.

The plot’s main concerns are with Batman trying to figure out the identity of the Phantasm, a mysterious new vigilante killing mob bosses in Gotham. Meanwhile, Bruce Wayne is reacquainting himself with long-lost former paramour Andrea Beaumont, back in Gotham after spending time abroad. Spoiler: Andrea Beaumont is the Phantasm and she’s killing the old mafiosos as revenge for their involvement in her father’s death, which drove her from Gotham and away from Bruce.

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Early on, we see Bruce Wayne deep into his playboy shtick, fending off the advances of multiple women. He gets asked if he’s ever thought of marriage but another woman discarded by Bruce offers a bitter answer, punctuated by throwing a glass of wine in his face. This sequence falls into the familiar thematic use of romance-as-feint in Batman history but then veers away from familiarity. We next see Bruce reminiscing about lost love Andrea, which in and of itself is a rare occurrence in the Bat-mythos.

As the movie moves back and forth between past and present, we see a younger version of Bruce, having just returned to Gotham after his training, ready to begin his mission to fight crime, but unsure how to do it. On a visit to the cemetery, he first meets Andrea at the graves of their parents, and immediately feels a kinship. Soon they’re going out on dates, and being playful with each other.

Setting a first-love storyline in Bruce’s formative adult years is a brilliant move. Pre-Batsuit Bruce is still trying to honor his childhood vow to fight crime, and he questions whether he can pursue both love and “The Plan” at the same time. That doubt shows how the relationship heightens the risk and stakes of Bruce’s mission, but more importantly, it gives him a glimpse of a life that he could never have imagined as a grief-stricken kid. It’s an important window into how love can change our lives and how we think of them. Mask of the Phantasm’s most powerful scene happens in front of the Waynes’ graves when Bruce gets overwhelmed by the competing desires for love and justice.

The rupture of that romance acts as a final push toward his becoming Batman, which makes his decision to devote his entire life to being a masked vigilante even more tragic.

Most painful of all is the miniscule glimmer of hope that hovers over the movie’s final third. Batman and Andrea have a bitter-then-sweet reunion, and you could almost imagine the hero pulling her away from the darkness that made her become the Phantasm.

But she’s too completely committed to her own version of “The Plan,” having made the choice that Bruce made years ago for the exact same reasons. It’s clear that their love for each other still exists but it’s not enough to save their damaged souls.

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None of the live-action Batman movies have ever managed to use romantic drama this well. Most of them have had love interests who’ve felt perfunctory and ornamental. In the comics, the most notable exceptions to the overall dysfunction of Batman’s love life have been Catwoman, Silver St. Cloud, and Talia al Ghul. There’ve been other women in Bruce’s life, like Julie Madison or Vicki Vale, but those aforementioned three have most impacted his life. His entanglement with Talia al Ghul made him a father, while his current go-round with Catwoman has had him propose to her.

The relationship between Andrea Beaumont and Bruce Wayne reminds me most of the one Bruce had with Silver St. Cloud in the classic Steve Englehart/Marshall Rogers run. Silver figures out that Batman and Bruce are the same person and eventually leaves Gotham of her own volition, because of the stress of what she knew and what it meant. She effectively dumps Bruce, not unlike how Andrea leaves him after he proposes in Mask of the Phantasm. Somehow, it’s sadder when the cold-hearted Batman is the one that gets walked away from.

Bruce Wayne created the Batman identity from a place of pain, deciding to sacrifice his own personal happiness and well-being for the greater good. There’s an element of love in that formula but not one that could stop him from feeling lonely. Mask of the Phantasm teases the audience with the possibility of a romance with someone who knows his secrets and shares a parallel drive for vengeance—then cruelly tears it away, adding another layer of pathos to the Dark Knight’s existence.