Dick Grayson is one of the biggest heartthrobs of the DC Universe. Women want him and men… also want him. Plus, he has this uncanny ability to stay friends with most of his exes after whatever form of relationship they had ends. This doesn’t mean that all of these were great experiences for the one-time Boy Wonder, though. Some of these women have been true loves of his life, while others would simply use Dick as a means to an end.
From Batgirl to Liu, Starfire to Raven and Cheyenne Freemont to Tarantula, the list of women for Dick is numerous, but (perhaps un-ironically for a former trapeze artist) not without gravity. Dick Grayson is the kind of character who will love whoever he chooses to be with completely, only in certain special instances will old flames prevent him from trying with someone new. None of these characters are “conquests” for Dick because he respects and truly cares for each of these women, except one, but we’ll get into her later. Dick Grayson’s relationships have been good, bad and sometimes even straight up weird (we’re looking at you Raven) but for the most part they are an intricate part of the character.
** SPOILER ALERT: Spoilers for the current Nightwing run **
15. CHEYENNE FREEMONT
Cheyenne Freemont was a popular fashion designer and also a metahuman. She and Dick bumped into each other and had a one night stand. While not Dick’s normal sort of fling, the pair wound up bumping into each other again. When next they met, Dick had been hired to be a runway model for her new line, in a Nightwing costume. After witnessing a fight between Dick and someone else dressed as Nightwing (Jason Todd), Cheyenne had the thought that Dick’s moves were much too fluid and true to not be genuine.
After finding out Dick is Nightwing, Cheyenne reveals that she is a metahuman and he tries to convince her to use her powers for good instead of hiding them. While Cheyenne does wind up using her powers and using one of her own Nightwing costumes to help Dick fight against the Pierce brothers, she hangs up her suit right after.
14. SHAWN TSANG
Originally going by the name Defacer, Shawn Tsang did her time and moved to Bludhaven to start a new life. Then Nightwing moved to town and her life started going from pretty good, to hell in a hand-basket. The recent arc reintroduced some lesser-known villains such as Orca and Dr. Simon Hurt, and really helped breathe new life in them while providing Dick and Shawn good antagonists.
After said hell, Shawn and Dick started dating and really hit it off, the two becoming one of the best in recent years and culminating in what appeared to be a pregnancy. Although the pregnancy turned out to be false, the two remain together currently, although things seem to be a bit rocky, and we’ll have to wait and see how the relationship turns out.
From the first time Dick laid eyes on Zatanna in Young Justice he was hooked. Interrupting M’Gann’s own introduction, Dick offers himself up to show her around the mountain and flirts with her relentlessly. After her father Zatara offered himself up to Nabu, the entity living in the Dr. Fate helmet, Zatanna moved into the mountain and Dick stayed with her longer than anyone to make sure she was going to be okay.
Not long after, Zatanna gave Dick a kiss on the cheek for his birthday, then a much deeper, passionate one on New Year’s Eve. Though not much is known about the relationship past there, except that they broke up during the time skip, the pair continued to be friends and still feel for each other.
Barbara Gordon, depending on who you ask, is the true love of Dick Grayson. The two always seem to be pushed together… before (somewhat maddeningly) being pushed away from one another. While it’s debatable if Babs is his true love or not, she is definitely one of the lasting loves and driving forces in his life. Plus, they are close enough that she can identify him by looking at his butt (not joking, this happened).
While the genius Babs is the one who broke off the relationship with Dick, the two remain star-crossed lovers who will always be there for each other. With her fairly recent return to the Batgirl mantle, who knows what the future holds for the couple. Will the two ever reconcile and pick up their romance? Only time will tell.
The Tamaranian Princess Koriand’r was with Dick for a long time, mostly as the two were members of the Teen Titans. The pair had a very hot and heavy relationship and were even about to be married when an evil Raven showed up, destroyed the wedding and killed the priest before he could pronounce them man and wife.
Starfire and Dick wound up calling it quits not long after this because Star felt that Dick did not want her forever, and Dick wasn’t able to deny that. While the two did truly love each other, their split brings Starfire to a lower slot for many fans in terms of who his true love might be, because Starfire’s love for him was simply not reciprocated the same way.
10. RAYA VESTRI
Raya and Dick met when the two were in Haly’s circus together, before Dick’s parents were murdered at the hands of Tony Zucco. Years later, after he had become Nightwing, Haly’s circus came back to Gotham. After being reunited, Raya tells Dick that they need to go to Atlantic City to see Mr. Haly. On his deathbed, Mr. Haly left the circus in its entirety to Dick.
On the train back, Raya and Dick shared a night together, but this is really as far as the relationship went. It was soon revealed that Raya was involved in a plot to not only get revenge on Dick from an assassin names Saiko, but to destroy the circus as well. Helping an assassin try to kill a man kinda puts a kink in relationships… and not the good kind!
Nightwing/ Huntress was another random one-night stand that happened. Dick even tried to ask about a relationship after the fact, stating that casual isn’t really his thing, only to be immediately shut down. Huntress at this point in time was looked at as bad news, so in order to keep the ex-Boy Wonder out of trouble with Daddy dearest, she told him that it was a matter of the pair being lonely at the same time.
While nothing more really happened with this pair, there was certainly some potential with it — possibly a story line where Dick decided to pursue a relationship? Suitable drama could have pitted the Bat-Family on either side of the relationship! Alas, we shall never know that story… at least not for now.
8. SONIA BRANCH (ZUCCO)
Dick’s only problem with Sonia, unfortunate as it is, is that her father killed his parents. The two were attracted to each other, and even shared a kiss, but when this kiss happened, Dick was flooded with images of her father, his parents, the circus and the life that he lost because of her father’s actions.
This could have very easily been another relationship that could have gone places with a story arc based on either his decision to be with her or not, but relationships don’t seem to sell comic books these days, so we barely ever get a comic focusing on the budding romance between characters. It is because Sonia is the daughter of Tony Zucco that this particular idea could have had a good story, but also why it will probably never happen.
Behold, the woman who took the virginity of Dick Grayson. As mentioned earlier, Dick is a very heartfelt individual. If he cares for someone, he cares completely and almost nothing can get in the way of that; a weakness that was seen and exposed by Liu and her partner Metal Eddie. Liu slept with Dick for the sole reason of trying to use him for his connection to Bruce Wayne and to be closer to access of Waynetech.
This betrayal, when revealed, tore Dick apart at the seams. It is widely believed that what Liu did to him is why Dick cannot seem to commit or stay with most women for an extended amount of time. He always puts up his walls and cuts women off before they get too close.
Tarantula is by far the worst of the worst Dick-lovers on this list. Dick never really wanted anything to do with her. She was first brought to Dick’s attention when she hit him during a self-defense class that he was teaching. She wanted to learn more advanced hand-to-hand combat, but also to get to know Dick on a more personal level.
After a series of attacks on his loved ones that was orchestrated by Blockbuster, Nightwing had an all-out brawl with him that ended in Tarantula killing Blockbuster, a murder Nightwing could have stopped. Realizing this, Nightwing lost touch with himself and fell to the ground, this was so much that he was unable to stop Tarantula as she raped him where he fell.
Nightwing / Catwoman was… weird. It was literally a physical thing that happened simply because she wanted to try and make Batman jealous. Of course, Dick calls her on this immediately, bursts out laughing and is promptly punched in the face, but it was funny nonetheless. The whole thing went down in a warehouse full of people trying to shoot them, and while Nightwing is trying to make her be serious about everything, she’s just trying the whole time to get into his pants.
The weirdest thing about this is the father-son aspect of Catwoman’s jealousy scheme. Why use your on-again-off-again boyfriend’s SON as your target for jealousy? Better yet, who in their right mind thinks that Batman can get jealous?
4. AGENT 8
For Agent 8, who first appears in Grayson #3, everything with Dick was about the job. She was an Agent of Spyral at the same time as him and was assigned to help him shoot better, essentially. Of course, the two wind up sleeping together after a bunch of teasing, and while it may have meant something to Dick, Agent 8 was just trying to drive a wedge between Dick and Spyral because she was a double agent for Leviathan. She even went so far as to fake her own death and act as Dick’s double at one point to frame him for murder.
3. DAPHNE PENNYWORTH
First appearing in Batman #216 and not being seen since Batman #227, Daphne was an actress by trade who worked with the Old Avon Players, in a not so similar fashion as her uncle Alfred. The Players threatened Daphne’s Father, Wilfred, if she did not go along with a plan of theirs to steal an original copy of “Romeo and Juliet” from Wayne Manor.
Going along with the plan so she could make sure her father was not hurt, she won over everyone in the Manor using her acting ability, especially Dick Grayson, who grew very taken with her. Although not much more happened here, it was one of the first portrayed instances of Dick liking someone not normal to continuity. Although true love didn’t blossom, at least we got to meet some of Alfred’s family.
Miriam Delgado comes from the future and was in a romantic relationship with the Nightwing of that time (a man who was later revealed to not be Dick Grayson. In her world, she worked with the Team Titans to fight against Lord Chaos, and when she was given the opportunity to go back 10 years in the past for a mission, she jumps at the chance.
Miriam then used her powers of being able to look like anyone to shift into Starfire, and used this ability to have a one night stand with Dick, who she thought to be the younger version of the man she was involved with. While this was the extent of Dick’s involvement with Mirage, it begs the question of how could Dick not tell it wasn’t actually Starfire?
Raven definitely takes the cake for the weirdest on our list. Aside from an innocent kiss, nothing ever actually happened in the romance department between Dick and Raven. When Raven was learning how to feel her emotions, as opposed to doing her best to keep them at bay, she started to feel as if she was in love with Dick. These feelings, mixed with Raven’s power, manifesting as dreams in Dick’s head where the two would be together in “all kinds of ways.”
Obviously, these feelings were implanted on accident and were never real for Dick, so there was never really going to be any kind of future there. Raven was able to realize what she had been doing and stop, and the two continued on as friends.
Which romance – good, bad or ugly — do you think was Nightwing’s most memorable? Let us know in the comments!