WARNING: Contains Potential Spoilers for Robin story in DC's Lex and the City #1!
Red Hood has had his fair share of romances in canon—the most notable of which will be explored in this article. However, none of these relationships have lasted in any meaningful way, often ending shortly after they begin. Now, Damian Wayne is finally providing readers with an answer to why his older brother will likely end up forever alone.
DC’s 2025 Valentine’s Special, Lex and the City, is an anthology that collects eight short stories, each following some of DC’s most iconic heroes and villains and the theme of love. Among these tales is the Robin-centric story To Live and Date in Gotham by Brendan Hay, Stephen Byrne, and Carlos M. Mangual.
This narrative follows Robins Damian Wayne and Tim Drake, with Damian seeking dating advice from his older brother. Damian also reveals why he chose Tim over Dick or Jason, and the reason he gives for not turning to his second-oldest brother is not only hilarious but also sheds light on why Jason Todd will likely never fall in love.
Damian Wayne Calls Jason Todd Out on His Dating Habits
Comic Comes from DC’s Lex and the City #1 (2025) – Story: To Live and Date in Gotham – Art by Stephen Byrne
In To Live and Date in Gotham, Damian approaches Tim and his boyfriend Bernard, asking Tim for dating advice. Initially, Tim declines, believing that others are better suited to help the youngest Wayne and suggesting, “Go ask another Robin.” However, Damian quickly dismisses this idea, explaining, “Dating is different for them. Dick is too handsome. Stephanie is too female. And it’s obvious that Jason only has one-night stands.” While these observations offer an interesting perspective on the other Robins, Damian’s take on Jason’s dating habits is particularly humorous and enlightening.
Since Tim doesn’t contradict Damian’s assessments of the other Robins, it’s safe to assume he agrees with them. This provides readers with a clear confirmation from both characters that Jason Todd, a.k.a. Red Hood, doesn’t date in the traditional sense—he resorts to one-night stands for his romantic needs. If this is truly Jason’s approach to romance, it suggests fans shouldn’t expect him to settle down with a true love interest anytime soon, or perhaps ever. After all, one-night stands rarely lead to lasting relationships. The fact that Jason’s past romantic encounters have been short-lived only further s the idea that love may not be in the cards for the big, bad Red Hood.
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Red Hood’s Love Interests Throughout the Years
Image Shows Red Hood Flanked by Batgirl Barbara Gordon & Artemis of Bana-Mighdall
Unlike the other adult Robins, Jason Todd is the only one who hasn’t experienced a character-defining romance. Dick Grayson’s relationships with Batgirl Barbara Gordon and Starfire are among the most iconic in comic book history, playing a major role in his character development. Similarly, Tim Drake’s relationships with Bernard Dowd and Stephanie Brown are also seen as pivotal to his character arc, and vice versa for Stephanie when it comes to Tim. Yet, when it comes to Jason Todd, the anti-hero has yet to have a romance that is both long-lasting and integral to his character, making him the odd Robin out.
That’s not to say Red Hood hasn’t had his share of romantic interests. Throughout various continuities, Jason’s most notable explicit or implied relationships include: Rena, his post-Crisis first love, whom he met while still Robin and briefly dated in Detective Comics #564 (1986); Talia al Ghul, a controversial romance due to their age difference, Jason’s vulnerability during their time together, and Talia’s role as a primary love interest of his adoptive father, Bruce Wayne (a.k.a. Batman); and Batgirl Barbara Gordon, another controversial Batman: Three Jokers (2020).
The list of notable love interests doesn’t end there. In 2011’s Red Hood and the Outlaws, there was implied romantic tension between Jason and Starfire, which sparked controversy due to Kori’s past with Nightwing. The series also introduced Essence as a romantic interest when Jason was part of the All Caste, as well as Isabel Ardila, a flight attendant who had recurring romantic involvement with him. Red Hood and the Outlaws further explored Jason’s relationships with Ravager (Deathstroke’s daughter Rose Wilson) and teammate Artemis of Bana-Mighdall, both of whom were featured as love interests. However, despite these many romances, they were all short-lived and never approached the depth of the character-defining relationships seen with the other adult Robins.
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Who Was Red Hood’s Best Love Interest?
Cover B Card Stock Variant by Francis Manapul for Robin #4 (2021)
When it comes to Red Hood’s best match, it likely comes down to Rose Wilson. Their past relationship was featured in Red Hood and the Outlaws #39 (2015), but their true compatibility was showcased in Tom Taylor’s DCeased, a zombie-apocalyptic Elseworlds story where the two stood side by side, fighting for survival. This series brought real heart to their relationship, highlighting their banter, camaraderie, and even receiving approval from Deathstroke. Unfortunately, the series didn’t have a happy ending for the couple, but this only deepened the emotional resonance of their love, making it all the more profound.
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Will DC Ever Give Red Hood a Long-Term, Character-Defining Romance?
Yasmine Putri Variant for Red Hood: Outlaw #27 (2018)
Red Hood’s sporadic and short-lived romance history, coupled with one of his brothers confirming that he isn’t the dating type and prefers one-night stands, raises the question of whether DC will ever give Red Hood a long-term, consequential romance. While there’s always the potential for a writer to come along and transform Jason’s character in this way, it seems unlikely—at least in his current state within the comics. Given that Red Hood doesn’t have an ongoing title at the moment, and with no indication of one on the horizon, it’s highly unlikely that a love interest will be introduced anytime soon.
That said, this isn’t necessarily a bad thing. Red Hood being single is perfectly acceptable, and there’s no pressing need to introduce a romantic interest for his character right now. Jason’s character is compelling enough on his own, with strong platonic relationships within his family that keep him well-rounded and grounded in mainstream continuity. Honestly, given how previous romantic attempts for Red Hood have fizzled, keeping him single might be the best choice for the character. After all, not experiencing romantic love isn’t inherently negative, as there are many other types of love DC can explore with Red Hood.
DC's Lex and the City #1 is available now from DC Comics!
