Who Did The Riddler Truly Love? An Analysis of Batman‘s Puzzle-Obsessed Nemesis

As an avid gamer and Batman enthusiast, one question has always fascinated me about Edward Nygma, a.k.a. The Riddler – who did this mastermind villain actually love? At first glance, the answer seems obvious: no one! The Riddler clearly has some severe attachment issues that stem from a tragic past involving parental abuse and rejection.

However, when analyzing key storylines across Batman mediums, some intriguing possibilities emerge on who the Riddler felt drawn to, even if those connections were toxic or one-sided. In this article, I‘ll explore the evidence behind four potential "love interests" for the Prince of Puzzles to provide the most compelling answer to who won this rogue‘s heart!

Batgirl: An Intellectual Attraction

In the 2018 comic Batman: Prelude to the Wedding, the Riddler encounters Batgirl while she‘s investigating a museum break-in he had orchestrated. As they face off, Nygma unexpectedly declares his love for Barbara and describes her as the only one capable of matching wits with him.

For the Riddler, I believe this "love" represented his acknowledgement of Batgirl as a worthy intellectual opponent. Edward has a pathological craving for validation of his genius – he wants to perpetually prove he‘s the smartest in the room through his elaborate puzzles.

So to him, Batgirl earned adoration by solving his schemes, indicating her high intellect. This briefly placed her above even Batman in the Riddler‘s eyes as the ultimate validating figure.

Key Evidence:

• Riddler creates "Riddle-Maze" at museum to challenge Batgirl specifically
• Calls her the sole person who could be his "intellectual counterpart"
• May have been partially strategic manipulation on his end

While certainly inappropriate, this incident reveals the Riddler‘s core need for intellectual validation – a "love" of having his brilliance recognized. In his disordered mindset, defeating and outsmarting the heroes is distorted into affection.

Kristen Kringle: The One Who Rejected Him

Kristen Kringle was a record-keeper working for the Gotham City Police Department – and also Edward Nygma‘s girlfriend in the TV show Gotham. However, after Kristen discovered Ed had secretly murdered her abusive ex-boyfriend, she broke ties with him.

This rejection triggered an emotional breakdown in Ed, causing him to accidentally strangle Kristen to death in a fit of rage. Here we see the Riddler‘s extreme attachment issues emerge.

Key Details on Kristen Kringle:

• Originally helped Ed solve riddles/puzzles as part of his therapy
• One of few people who validated his intelligence
• Rejected Ed after learning he killed her ex

Once again, the catalyst for this relationship was the Riddler‘s craving for validation. Kristen provided that through solving his riddles, making her an object of affection.

When she withdrew that validation due to his criminal actions, it decimated Ed emotionally. This reveals how completely destabilizing losing his sense of intellectual superiority is for him.

Oswald Cobblepot: A Warped Friendship

In that same Gotham series, fans noticed intriguing chemistry between the Riddler and Penguin. The show explored a budding friendship but also hinted at stronger feelings, especially from Penguin toward Nygma.

Complex bonds between villains are a recurring theme in Batman lore. While the Riddler and Penguin often collaborate, they‘ve just as frequently turned on each other when agendas conflicted.

Highlights of Their Relationship Journey:

• Both outcasts who found acceptance in each other
• Riddler helped Penguin enact revenge schemes
• Jealousy emerged after Penguin became "King of Gotham"
• Their partnership imploded in the "War of Jokes and Riddles"

Ultimately Riddler and Penguin connected due to being societal rejects – both felt looked down upon and underestimated by fellow rogues and Batman himself.

But the egotistical Nygma struggled to tolerate Penguin rising to power in Gotham‘s criminal underworld. At best, this relationship represented a companion friendship between two villains, not genuine romance.

The key takeaway is that for the Riddler, no emotional bond will ever override his ego-driven thirst for greatness. He‘ll always prioritize his criminal plotting above all else.

Batman: The One True Obsession

If we analyze all of the Riddler‘s storied history, what name appears connected to him most often? That would be none other than Batman/Bruce Wayne himself.

The Riddler‘s Compulsion to Outsmart Batman

• Motivated by abusive father underestimating his intelligence
• Batman = ultimate figure to prove his superior intellect to
• Crimes revolve around elaborate death traps/puzzles to defeat the Dark Knight
• Gets enraged if Batman doesn‘t personally respond to his challenges

This shows that overcoming his archenemy serves as the Riddler‘s ultimate psychological validation. In his disordered mind, if he can outwit Gotham‘s greatest detective, then his genius is irrefutably real.

So perhaps in an twisted way, Batman indeed represents the Riddler‘s one true love – the puzzle-solving adversary he perpetually chases to feed his pathological craving for self-worth. It‘s an undoubtedly toxic obsession, but also the closest bond Edward Nygma has ever achieved.

Ultimately the Riddler remains incapable of genuine love or redemption. For him, pursuing validation through criminal puzzles will always eclipse emotional connections. And as long as Batman fights for justice in Gotham, his never-ending quest to outsmart the Dark Knight will continue.