Batman has certainly had his fair share of love interests, but his first Robin, Dick Grayson, gives him a run for his money. After dropping the Robin identity and leaving Gotham for Blüdhaven, he took up the mantle of Nightwing. As a solo act, Grayson became quite the heartthrob across DC Comics.
Known by heroes and villains alike as the smart and quick-witted crime fighter, Dick has a solid list of love affairs during his long comic run. His history with Barbara Gordon, aka Batgirl, aka Oracle, is well documented, but some other entries may surprise you.
Shawn Tsang, Debut: 'Nightwing' Vol. 4 #10 (2017)
Tsang was formerly known as the criminal, Defacer, and she had several run-ins with Batman and Robin, when Dick was the Boy Wonder. After giving up her criminal lifestyle, she moved to Blüdhaven, where she lived a normal life before being captured by Professor Pyg.
After being rescued by Nightwing, they had a brief relationship that ended due to her past as a criminal and distrust of superheroes. However, both admitted they had feelings for each other before acknowledging that it wouldn't work.
Bea Bennett, Debut: 'Nightwing' Vol. 4 #50 (2018)
Bea is a local bar owner in Blüdhaven that supported Dick Grayson, going by Ric Grayson, after he suffered a traumatic gunshot wound to the head and had no memory. She was even giving him a place to live.
The two connected over a mutual interest to aid the homeless and poverty-stricken people in Blüdhaven, including working in homeless shelters. They eventually became an item, but when "Ric's" past caught up with him, he ended their relationship to protect her.
Helena Wayne, Debut: 'DC Super-Stars #17' (1977)
This one is a bit different from the rest, taking place on the Eart-2 continuity. Helena Wayne is the identity of this Earth's Huntress, and also the biological daughter of Bruce Wayne and Selina Kyle, Catwoman, which technically makes Dick and Helena foster siblings.
In this continuity, Dick and Helena married and had a long relationship, but their world was destroyed during the Crisis event, and eventually they were both wiped from continuity, and Helena Wayne was recreated as Helena Bertinelli.
Bridget Clancy, Debut: 'Nightwing' Vol. 2 #2 (1996)
Clancy and Grayson became very close, very quickly once Dick made the move from Gotham to Blüdhaven. Clancy was the superintendent of the apartment building that Dick was renting out of, so naturally their paths crossed quite a bit.
Both displayed a mutual interest in each other, but during their almost romance, Dick sparked up his long-standing will-they-won't-they relationship with Barbara Gordon.
Cheyenne Freemont, Debut: 'Nightwing' Vol. 2 #118 (2006)
Cheyenne Freemont is a meta-human that had quite a run in with not just one former Robin, but two! Freemont has powerful telekinetic powers, but keeps them hidden due to the discrimination she faced as a child with her parents.
After a romantic entanglement with Grayson, Freemont came face-to-face with Jason Todd before Dick came to her rescue. Dick learned she was a meta-human, and she learned he was Nightwing. Todd later was captured, and Freemont, donning a costume similar to Nightwing's, teamed up with Dick to save him using her powers.
Bette Kane, Debut: 'Batman #139' (1961)
Bette Kane was the niece of DC's Batwoman, Kathy Kane. However, her origins weren't necessarily born out of pure creativity, so to speak. Kane was created to be an early love interest for Dick Grayson because the writers began to worry about Batman and Robin's perception.
Bette was reintroduced later on in DC's run, and was given the name of Flamebird/Hawkfire. During this new run, she did not become romantically involved with Nightwing, but rather he was her idol.
Helena Bertinelli, Debut: 'The Huntress' #1 (1989)
Better known as Huntress, the romance between Helena and Dick didn't start naturally, but rather with ulterior motives for the markswoman. She planned on getting close to Nightwing in an attempt to infiltrate the Bat-Family, but caught feelings for him instead.
They did have a one-night stand and a brief romance, but later on Helena attempted to reconcile with Dick, and assure him the feelings were real, which he shut down (after they kissed). But its clear Dick has unresolved feelings for her.
Zatanna, Debut: 'Hawkman' #4 (1964)
Zatanna is a magic user that is considered to be one of the strongest in all of DC. However, she and Dick only dated in their Young Justice appearances, and remained Platonic in the comics. They flirted a bunch, and it was clear there was a romantic connection.
Fans didn't even get to see their breakup, or even their full romance, on the show, but they both remained close friends throughout. The Boy Wonder has the skill of keeping close relationships even after a breakup.
Starfire, Debut: 'DC Comics Presents' #26 (1980)
A fellow member of the Teen Titans, Koriand'r, aka Kori, aka Starfire, is arguably Dick Grayson's most significant relationship. Due to their longevity and how much time they've spent together as members of the Titans, they essentially grew up together.
Starfire is one of the most powerful members of the Titans, with the ability to project bolts of energy, fly, and of course, her super strength. It's certainly one of the most prolific relationships in comics, and has made its way into other media like the DC Animated Universe.
Barbara Gordon, Debut: 'Detective Comics' #359 (1967)
Dick's relationship with Babs has been well-documented. With most of their mutual attraction coming during their time as Robin and Batgirl. Dick's ongoing relationship with Starfire made things complicated for the young caped crusaders to ever officially be a couple.
Dick even proposed at one point, but it never really seemed to work out at the time for these two, perhaps a case of "right person wrong time." Eventually, thankfully, they got together. Both individually and as a couple, these characters are some of the best DC has to offer.