One of the more interesting hero love lives belongs toGreen Arrow. Oliver Queen is best known for dating and eventually marrying Black Canary Dinah Lance, but it cannot be overlooked that the billionaire has always hada complicated playboy lifestyle. These two have been together for so long that it may feel like they were always together, but that’s far from the case.
There were times when Oliver found himself either pining for someone else when he wasn’t with Black Canary.Honestly, there were times when he found himself lusting over other suitors even while he was with Dinah. Sometimes, the two would have a rocky relationship and sometimes, Ollie was the farthest from a faithful man. Green Arrow’s faithfulness and his battles with fidelity were once a constant character flaw for him, but it also gave birth to numerous fascinating love interests who weren’t Black Canary.

9Skylark
Green Arrow#6 by Keith Giffen, Dan Jurgens, Ignacio Calero, Ray McCarthy, Tanya Horie, Richard Horie, and Rob Leigh
Technically, this is a three-way tie, because Skylark is a name shared among three triplets.More than just a triple threat, the Skylark trio were practically Catwoman - if Catwoman were spliced into three people.A man of Green Arrow’s ilk couldn’t help but fall into Skylark’s “honey trap.”
The three seduce Oliver upon meeting and forming their alliance, only to betray him and get everything they wanted from him when the time was right.

Most superheroes have one femme fatale in their life, but technically, when it comes to Skylark, Green Arrow has three all at the same time. The DC Universe is filledwith strong female characters, anti-heroes, and complicated villains. Skylark ranks among the more unique, making for a one-of-a-kind love interest for Oliver Queen.
8Blood Rose
Green Arrow#3 by J.T. Krul, Dan Jurgens, Keith Giffen, George Perez, Ray McCarthy, Tanya Horie, Richard Horie, and Rob Leigh
Even supervillains need sidekicks, and for Midas, that sidekick was Blood Rose.Upon first confrontation, Blood Rose proved to be an impressive fighter and markswoman before showcasing unreal levels of strength.After further inspection, Oliver learns that this woman is a robot. The story soon reveals that Blood Rose aligns with her new criminal/romantic partner, Midas, because she is planning revenge against her former lover, Oliver Queen. Neither knows that Green Arrow and Oliver Queen are the same, making the archer’s meddling a mere inconvenience for her.
While their actual romance took place off-panel before the events of the comic, it makes for an interesting backstory that creates a complex character. It doesn’t allow the reader to invest much in their relationship when one doesn’t exist on-panel, but it creates investment for Blood Rose in her revenge mission, which readers can actually invest in out of intrigue.

7Manitou Dawn
JLA#75 by Joe Kelly, Doug Mahnke, Yvel Guichet, Darryl Banks, Dietrich Smith, Tom Ngyuen, Mark Propst, Wayne Faucher, Sean Parsons, David Baron, and Ken Lopez
As much as Green Arrow practically jumped at the chance to date a Justice League teammate when he fell in love with Black Canary, that wouldn’t be the last time that he’d make such an exception.He dated another fellow Leaguer in Manitou Dawn,one of the oldest Justice League heroes. The 3,000-year-old was married to her husband and fellow Leaguer, Manitou Raven, when she began an affair with the Green Arrow.
As a wedge was forming with her husband, Dawn confided in Oliver as a friend, which turned into a sexual relationship.It never evolved into anything serious or truly romantic, hence why it was easy for the two to go their separate ways when their hooking up was exposed to the rest of the League.It’s almost ironic to see Oliver play “the other man” for once when he has a history of cheating on Dinah.

6Joanna Pierce
Green Arrow#26 by Judd Winick, Phil Hester, Ande Parks, Guy Major, and Sean Konot
Since Oliver is madly in love with Black Canary today, don’t expect him to ever namedrop Joanna, someone he was smitten with when he just got back together with Dinah back in the day.Joanna Tanner has some interesting roots in the DC Universe, as her father was Two-Bits, a frequent snitch to Black Lightning, while her mother was Connie Pierce, Black Lightning’s sister. Joanna’s upbringing in the Suicide Slums eventually saw her relocate to Star City as a lawyer.
The two quickly hook up after meeting, but she breaks it off when she finds out about Dinah, and within four issues of being introduced, Joanna has been killed by Constantine Drakkon,one of DC’s deadliest assassins.Still, that Green Arrow found himself so enamored with her that he was willing to put his romance with Dinah at risk says a lot about her character.He failed Joanna, and, unsurprisingly, Dinah wasn’t happy to hear that he had cheated on her.

5Hyrax: Veronica Dale
Green Arrow#97 by Chuck Dixon, Rodolfo Damaggio, Gerry Fernandez, Frank McLaughlin, Rob Leigh, Lee Loughridge, and John Costanza
The name Veronica Dale may sound familiar to Arrowverse viewers who watched the Season 4 “Enter Flashtime"episode ofThe Flash.While she showed up as a villain in a one-off episode, she plays a much larger role in the DC Universe - not in Barry Allen’s rogues gallery, but in Oliver Queen’s. Much like in theFlashepisode, Hyrax is an eco-terrorist leading the Eden Corps.
She has a bomb planted in Metropolis, receiving a bullet for her troubles, hoping her last breath would allow the bomb’s detonation, ridding the city of blight. Oliver sacrifices his life to save the city.

Oliver is a sucker for a villainess and couldn’t help but start a romance with this one as well.This character proved to be one of the deadliest villainesses in his life, though, and by proxy, among his most complicated relationships. She has a bomb planted in Metropolis, receiving a bullet for her troubles, hoping her last breath would allow the bomb’s detonation, ridding the city of blight. Oliver sacrifices his life to save the city.
4Chloe Sullivan
Smallville: Season 11#1 by Bryan Q. Miller, Pere Pérez, Chris Beckett, Randy Mayor, and Saida Temofonte
Any Superman fan who watched television back in the 2000s will have fond memories ofSmallvilleand that show’s original character, Chloe Sullivan, who was more or less Clark Kent’s equivalent to Oracle.She even adopts the name Watchtower when she assists the show’s Justice League from the shadows. She is best remembered for her fan-favorite love affair with Green Arrow, which continues inthe comic seriesSmallville: Season 11.
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At the show’s end, she marries Oliver Queen and a flash-forward reveals that they have a child together.While fans were glad to see the couple receive their happy ending, the story doesn’t end there. In the comics, not only is her pregnancy and childbirth witnessed in real-time, but she plays an important role in this universe’s version ofCrisis on Infinite Earths.

3Sandra Hawke
Green Arrow#91 by Kelly Puckett, Jim Aparo, Gerry Fernandez, Lee Loughridge, and John Costanza
Sandra “Moonday” Hawke was one of Oliver’s college girlfriends from before he became the Green Arrow.Their union gave birth to Connor Hawke, the second Green Arrow and, in Oliver’s mind at least,the best fighter in the world. Due to Oliver’s fears of being a father as a young man, the independent “hippie” character raised Connor alone as a single mother, though fate brought Connor and Oliver together when the time was right later in their lives.
Although her relationship with Oliver wasn’t meant to be for the long run, Sandra has entrenched herself in the DC Universe as an essential part of Green Arrow lore.That’s thanks largely to her birthing and raising the next Green Arrow, but she’s also a strong-willed character with her own merits outside of being in a superhero family.
2Tarantula: Catalina Flores
Nightwing#71 by Devin Grayson, Rick Leonardi, Jesse Delperdang, Gregory Wright, Digital Chameleon, and Willie Schubert
Catalina Flores is an interesting case, since her character is more closely tied to Nightwing lore than Green Arrow.She’s a former FBI agent turned controversial crimefighter working out of Blüdhaven as an anti-hero who kills. However,during DC’s New 52 rebootas a part of the Prime Earth continuity, she was a vital supporting player in Green Arrow’s ongoing comic.
She became a quick ally of Green Arrow’s when her hometown was taken over by the Bone Hunters, and through their adventure together, a romance bloomed.The series ends with Green Arrow and Tarantula sharing a kiss in the final panel of the book’s finale issue.The vigilante hasn’t been seen much in DC Comics since that era. Just as their romance started to heat up, DC revamped everything once again, and Tarantula was quickly forgotten without giving their dynamic a proper resolution.
1Black Canary
Justice League of America#75 by Dennis O’Neil, Dick Dillin, Joe Giella, and John Costanza
It should come as no surprise thatBlack Canary comes out on top as Green Arrow’sbest love interest. More than just positioned as Oliver’s greatest love story, this couple is viewed as thegreatest love story in DC history. What’s most impressive about this coupling is just how unexpected it was when it first came about. Their first few appearances together were uneventful, as a romance was never originally in the cards.
Merely being Justice League teammates eventually turned into flirtations, and even then,readers could never have predicted their romance to last for so many decades or become such an important part of DC culture. They’ve become essential to each other’s hero journeys. At this point in modern comics, it is hard to imagineGreen Arrowwithout Black Canary by his side - and vice versa.