Have you ever heard of Gilmore Girls? Well imagine a show called Grayson Girls starring all the girls who've captured Dick Grayson’s heart. There were some notable ones, and perhaps a few regrettable ones. Everyone makes mistakes in love! We recently looked at Bruce Wayne’s little black book, and now we’re going to check out Dick's. Did he make better choices in love? Was he a better boyfriend than his mentor? Let’s take a look!
Meet Cute: Empress Lanya might not be as iconic as Batgirl or Starfire, but she holds the distinction of being the first girl for whom Dick Grayson ever fell. It’s the classic “boy meets girl” story. She was the Empress of a hidden Atlantean society that had been taken over by Nazis, and he was an orphaned circus acrobat. Robin and Batman wound up stumbling across the lost city of Atlantis in 1943’s Batman #19, where Dick met Lanya and began his lifelong obsession with the opposite sex.
Boyfriend Blunders: We forgot to mention one weird thing: Dick was the exact double of Lanya's brother! He even disguised himself as her bro during this adventure.
Sinking of the Ship: This ship never officially left port, despite the young puppy love between the two youngsters. Once Atlantis was liberated from the Nazis, Batman and Robin returned to Gotham, with the Boy Wonder contemplating how he would never see his crush ever again. She did write him a cool goodbye note that he kept close to his heart. Maybe they can Snapchat?
Odds of Endgame: 20 to 1. Lanya has not been seen in decades, but you ever forget your first love.
Meet Cute: Dick met Marjory in school, where the Boy Wonder would lovingly stare at her during their classes. In 1944’s Batman #23 Marjory became Dick Grayson’s very first girlfriend, and he got ready for his first date by drenching himself in cologne. Apparently that wasn’t covered by Bruce in his crime-fighting training.
Boyfriend Blunders: Dick was very bad at hiding his secret identity from Marjory. As Robin, he sang the praises of Dick Grayson and hoped it would help endure Marjory to him further. When Marjory was kidnapped, Robin claimed Dick sent him to save her. Although Marjory was one of the brightest students in their class, she never caught on to Dick’s double life, despite his clunky clues.
Sinking of the Ship: Once Robin saved Marjory, it was all over for her and Dick. Marjory wanted nothing to do with Dick anymore and only dreamed of Robin the Boy Wonder. She did tell Dick she would continue dating him, but only if he set her up with Robin as well. Awkward.
Odds of Endgame: 10,000 to 1. She dropped Dick like a hot potato.
Meet Cute: Vera was a celebrity ice skater whom Robin saved in Batman #107. She holds the distinction of being Dick Grayson’s first kiss, which rocked his world so much that he became too distracted to fight crime effectively.
Boyfriend Blunders: Most of us were teenagers at one point, so we can relate to how young love distracts us from everything else. During Robin’s brief romance with Vera, he got sloppy with his crime fighting and begged Batman to cut their patrols short so he could spend time with his girlfriend.
Sinking of the Ship: Robin decided he needed to rededicate himself to justice, so, alas, Vera was never seen again.
Odds of Endgame: 500 to 1. She was his first kiss, and she could possibly be his last.
Meet Cute: Teenage athlete Betty Kane first met Robin in Batman #139 when she convinced her aunt Kathy “Batwoman” Kane to let her become Bat-Girl and join her on patrol. Bat-Girl was not shy about her attraction to Robin, which made the Boy Wonder super uncomfortable.
Boyfriend Blunders: He once told her he was cheating on her with a statue. (Seriously, if you ever stumble across Batman #144, that’s exactly what he does.)
Sinking of the Ship: As Batwoman and Bat-Girl became less active, the couple drifted apart. To be fair, Dick was never that into her in the first place, and once the next Batgirl came along, Betty was forgotten.
Odds of Endgame: 30 to 1. She’s still an active crime-fighter, and her feelings for Dick have never gone away. Could she yet be the Bat-Girl he ends up with?
Meet Cute: Dick met Lori when the two were enrolled at Hudson University, and they began dating in Detective Comics #450.
Boyfriend Blunders: Usually college relationships are when things start to heat up, but Dick was always leaving Lori so he could do Robin stuff. Once the mask was on, his relationship to Lori was forgotten and he wasted no time flirting with Batgirl. Not cool Boy Wonder.
Sinking of the Ship: Lori eventually got fed up with Dick, and began dating someone else. In Detective Comics #483, Dick violently beat up Lori’s new boyfriend in the middle of the campus and revealed that he was secretly part of a criminal organization. He even made a few references that only Robin would know, because his secret identity wasn’t as important as embarrassing Lori in front of the entire college. Lori was humiliated, and Dick walked away leaving her life forever.
Odds of Endgame: 52,000,000 to 1. He burned that bridge very effectively.
Meet Cute: Jennifer caught Dick’s eye in Detective Comics #488, so he stalked her across campus hoping he’d get the chance to introduce himself to her. He compared it to trailing criminals, which only made things weirder. Dick was still working on his social skills in the Bronze Age. She got kidnapped by some crooks, and he saved her as Robin, but he still made sure his civilian identity got some of the credit.
Boyfriend Blunders: When Dick was failing college Jennifer offered to say with him all night to help him study. Dick went to catch crooks instead. Sound familiar? When a beautiful co-ed says she wants to help your academic future, let her help you!
Sinking of the Ship: Dick flunked out of Hudson University in Detective Comics #495 and never saw Jennifer again.
Odds of Endgame: 500 to 1. Dick probably doesn’t even remember her.
Meet Cute: After Nightwing rescued Miggie from some kidnappers, he checked up on her at the hospital as Dick Grayson. Sparks flew, and Miggie became the first girl to get Dick back on the horse after his disastrous breakup with Starfire. They began a brief romance in 1995’s Nightwing #1.
Boyfriend Blunders: It’s obvious Miggie was going through something, but Dick found up leaving the country to get involved in a complicated murder mystery, leaving Miggie to spiral out of control.
Sinking of the Ship: By the time Dick returned to America, Miggie had murdered her abusive father. She was arrested, and Dick decided to cut his loses instead of researching the rules for conjugal visits.
Odds of Endgame: 150 to 1. A girl that could make you forgot about your breakup with a hot alien princess is something special. Maybe Dick can look her up if she’s ever released on parole.
Meet Cute: We’re not going to lie folks, this one is a bit messed up. Emily Washburn was a widow whose husbands kept dying under unusual circumstances. In Nightwing Annual #1 Dick decided to investigate her by PRETENDING TO MARRY HER. He courted her, he had her fall for him and he even bonded with her young son. They had a wedding ceremony and everything, and Dick made sure the proper paperwork was never filed.
Boyfriend Blunders: The entire relationship qualifies here, especially because a young kid was involved. Making someone believe you’re a family is pretty messed up, especially if you’re only in it to investigate them. Wouldn’t it have been easier to just dust for fingerprints?
Sinking of the Ship: It turns out she wasn’t the murderer, her best friend. Dick told her the truth about everything and Emily did not take it well. Dick offered to try having a real relationship with her, but Emily walked off. Could you blame her?
Odds of Endgame: 10,000 to 1. It would take a miracle for her to forgive Dick.
Meet Cute: Dick met Bridget Clancy in 1996’s Nightwing #2 when he moved to Bludhaven and rented an apartment in her building. Dick was intrigued by Clancy, but his busy life as Nightwing made it difficult to get their relationship off the ground.
Boyfriend Blunders: When Dick left girlfriends like Lori Elton or Jennifer Ann to go do superhero stuff, he usually made up some excuse. With Clancy he would just leave without saying a word. Seriously, in 1998’s Nightwing #26 she left the room for a moment, and when she returned Dick was already gone. He didn’t even pretend to come up with some flimsy lie.
Sinking of the Ship: Clancy and Dick grew closer, and they even shared a passionate kiss to celebrate him graduating the police academy, but by 2000’s Nightwing #43 he was forced to tell her difficult news. Dick’s relationship with Barbara Gordon had started to turn serious, and he told Clancy there was another woman. Although Clancy was heartbroken, she and Dick remained friends.
Odds of Endgame: 30 to 1. Dick did like Clancy, and they could have something special if things ever calm down.
Meet Cute: Huntress needed backup on a mission in 1993’s Black Canary #10, and requested that Oracle put her in touch with Nightwing. While the two got along well during their adventure, it wasn’t until the Nightwing/Huntress limited series that their friendship turned to passion.
Boyfriend Blunders: Some would argue that getting involved with Helena in the first place was a blunder. During her early days she was known for using lethal force and questionable methods, which put her at odds with Batman and the rest of the Bat-Family. Everyone from Barbara Gordon to Tim Drake gave Dick a hard time about this hookup.
Sinking of the Ship: Helena admitted that she only slept with Dick because she hoped he would help her become a member of Batman’s inner circle. For what it’s worth, Dick took the news in stride.
Odds of Endgame: 500 to 1 Nightwing doesn’t regret many relationships, but this one was a serious lapse in judgement.
Meet Cute: Dick first crossed paths with Catalina in Nightwing #71 when she attended a self defense class he was teaching. She brazenly asked for his phone number, which made Barbara Gordon jealous. Catalina eventually became the anti-hero Tarantula and initially worked with the crime lord Blockbuster to destroy Nightwing’s life. After Nightwing allowed Tarantula to kill Blockbuster in Nightwing #93, Dick went through a depression and in his funk he Catalina took advantage of Dick and forced him into an unwanted physical encounter.
Boyfriend Blunders: During a period where Dick was in a depressed funk, Catalina convinced him that they should get married for fun. They were seconds from tying the knot in Nightwing #95 before being interrupted by a phone call from Batman.
Sinking of the Ship: Dick came to his senses in Nightwing #100 and turned them both in for the murder of Blockbuster, effectively ending their partnership and romance.
Odds of Endgame: 5,000 to 1. Remember when we said Huntress was a mistake? This was an even bigger one.
Meet Cute: Dick moved back to New York City in Nightwing #118 and hooked up with Cheyenne during a lonely night. Both of them were hiding secrets, Dick was Nightwing and Cheyenne was a metahuman who could create energy blasts. She eventually used one of Dick’s spare outfits and became Nightwing alongside him.
Boyfriend Blunders: The arrangement was odd. Do they both call themselves Nightwing? Both wearing the same costume? Does that mean that Dick is basically dating himself?
Sinking of the Ship: Cheyenne preferred to keep things casual, and when she got a job offer in Hollywood In Nightwing #124 she cut ties with Dick and wouldn’t even allow him to drive her to the airport. Ouch!
Odds of Endgame: 200 to 1. Nightwing dating Nightwing is a bit weird.
Meet Cute: In Nightwing #140 Dick tried his hand at being a museum curator, where he met Deborah Poulos. Sparks flew and a short romance began.
Boyfriend Blunders: A series of attacks like Deborah feeling unsafe and Dick wasn’t too sensitive about it. Plus, he cheated on her with Starfire in 2008’s Titans #3.
Sinking of the Ship: Deborah’s PTSD made her feel unsafe in New York, so she left for a new life in Nightwing #151 and ended her romance with Dick.
Odds of Endgame: 4,000 to 1. Dick didn’t handle this one with care.
Meet Cute: Raya Vestri was a childhood friend of Dick’s from his time at Haly Circus. In 2011’s Nightwing #1 she caught up with him again as an adult. Now that they were both grown up Dick realized he was attracted to Raya and the two gave in to that attraction during a plane ride in 2011’s Nightwing #2.
Boyfriend Blunders: This should go without saying, but don’t have sex on a plane. It’s gross, it’s inappropriate and other people need to use those seats when you’re done.
Sinking of the Ship: Raya was secretly working with another circus friend named Raymond to destroy Dick’s life and the entire relationship was revealed to be a sham.
Odds of Endgame: 9,500 to 1. Even if Dick could forgive Raya, she was killed by the Joker in 2012’s Nightwing #15.
Meet Cute: Shawn Tsang was once the Defacer, young sidekick to a criminal called the Pigeon. During that time she had several run ins with Batman and Robin. She reunited with the adult Boy Wonder when he came to Bludhaven in 2016’s Nightwing #10. After helping her prove her innocence for a crime she was accused of, they began a whirlwind romance.
Boyfriend Blunders: 2017’s Nightwing #15 proved that Dick doesn’t know how to do a normal romance. The couple bickered about small stuff like open windows, and Dick making plans for them over a year in advance.
Sinking of the Ship: After a pregnancy scare, Shawn reevaluated their relationship and decided to call it quits in 2017’s Nightwing #25.
Odds of Endgame: 15 to 1. For what it’s worth, Dick really seemed to love her.
And now we’re saving the biggest two for last….
Meet Cute: The alien princess known as Koriand’r fled to Earth in 1980’s The New Teen Titans #1 where she took refuge with the Teen Titans. Her species uses skin to skin contact to absorb languages, so she kissed Robin passionately in The New Teen Titans #2. Although Dick ran from his feelings for her for a while, he eventually revealed that he loved her and a long romance followed.
Boyfriend Blunders: At one point when the two were on a break in New Titans #99, Kory went out on a casual date with another man. Dick showed up to their nightclub in his Nightwing costume and threw the other guy across the room.
Sinking of the Ship: After a failed wedding in New Titans #100, and Kory undergoing a life changing ritual in New Titans #109, the two drifted apart and couldn’t put the pieces back together again. Their breakup became official in New Titans #114.
Odds of Endgame: 2 to 1. Although they parted ways, their attraction to one another never truly died and they’ve hooked up again a few times.
Meet Cute: The legendary couple known as Dick/Babs first when Batgirl debuted and joined Batman and Robin in their hunt for Killer Moth in Detective Comics #359. Robin didn’t pay Batgirl any mind until she kissed him (to shut him up) in Batman Family #1. A lifelong crush was born, and Dick finally got Barbara to reciprocate his feelings in 1999’s Nightwing #38.
Boyfriend Blunders: Where to begin? There was the time when he asked her to erase a tape that would restore her memories (Detective Comics #489). Then there was the flashback in Nightwing Annual #2 where he slept with her and in the morning INVITED HER TO HIS WEDDING TO STARFIRE! Dick hasn’t always been bright.
Sinking of the Ship: After getting engaged in Nightwing #117, Barbara had second thoughts and returned Dick’s ring in Nightwing Annual #2. She told him that he still had to work on himself, and when he was ready for marriage she would be there waiting. They’ve almost gotten back together a few times, but their vigilante lifestyles have kept it from happening.
Odds of Endgame: 2 to 1. Dick and Babs are a force of nature and their love story could never truly be over.
Honorable Mentions: A few lovely ladies have caught Dick’s eye over the years, but not all of those relationships got off the ground. In 1954’s Batman #81 Dick was sweet on a high school classmate named Marcia, but she only had eyes for Robin. A girl named Edie was Dick’s date to a high school dance in Batman #156. Dick took a girl named Nancy to their high school prom in Detective Comics #340, but all he could think about was helping Batman fight the Outsider. Sandy Cole worked with Dick Grayson on their high school paper, and they briefly dated in Detective Comics #390-391. When Dick Grayson attended Hudson University, a computer dating service matched him with Terri Bergstorm in Batman #231. Terri later turned out to be the cousin of Robin’s Titans teammate Lilith. When Dick transferred to Gotham University, he became smitten with a classmate named Dala in Detective Comics #511. It appeared that they started dating, but it turns out she was using her vampire mind control powers to trap him. Dick was also tricked into a romantic encounter with he Team Titan known as Mirage when she shapeshifted as Starfire during the “Total Chaos” storyline. Nightwing #133-137 revealed that Dick had a teenage fling with a girl named Liu, who he claims he lost his virginity to.
WHEW! Dick Grayson did a lot more dating than we thought! Who do you think had the biggest impact on his heart?