Nightwing has long been known as one of the most successful sidekicks in comics, having not only graduated into his own identity but also successfully taking over for his mentor. One of the most beloved heroes in the DC Universe, Nightwing has always gotten along with the ladies, but one has held his heart the longest—Barbara Gordon, the woman known as Batgirl.
While Nightwing has had other lovers over the years, he often returns to Batgirl, as their experiences why they were young are quite similar. The two share a powerful bond, even if they might not be the best for each other.
10 Black Canary
While Black Canary is known for her relationship with Green Arrow, anyone who has been following the two's relationship for any amount of time knows that Ollie is a bit of a dog and not always worthy of Dinah's love. She deserves a man who would treat her right and Nightwing would be perfect for that.
The two of them would be very good together in general- Black Canary is one of the best fighters around, so they would be an efficient crime-fighting pair, and she would treat Nightwing very well- she's used to someone like Ollie who isn't nearly as easy to get along with as Dick Grayson. The two would be a formidable team and fill a place in the other's heart.
9 Zatanna
Zatanna is one of the most powerful magic users in the DCU. She's been associating with Batman for a long time, so there's a very good chance she and Dick known each other very well. Her supportive, bubbly personality would be just what Dick needs after some of his grimmer cases and the two would work well together on team-ups.
Zatanna hasn't always been on the straight and narrow and Dick would be able to help her with that, as he's one of the most solid heroes around. Together, the two would make a formidable team and have a fun relationship that would be good for both of them.
8 Wonder Woman
Wonder Woman is one of the strongest women in comics and a stalwart defender of the innocent. She's known Nightwing for a long time and watched him mature into a capable hero. While it might seem a little weird at first, the two would actually work out pretty well for each other. Wonder Woman is solid and dependable, loving with all of her heart and that's the kind of woman Dick needs.
As for Wonder Woman, Nightwing would help to mellow her out and get her to experience life in a different way than she's used to, that of a normal person. A relationship between the two of would help them both grow as people.
7 Huntress
Huntress has always been a weird one in DC continuity, with every version of the character being a bit of a tweak on the one before. Every version has had a relationship of some kind with Nightwing, with the latest version of Helena Bertinelli and Dick Grayson having a history together working for Spyral. Huntress has always been a more extreme vigilante and person and Dick could use that in his life.
Huntress would get Dick to embrace the more crazy side of life, taking him out of his comfort zone and getting him to grow as a person. A relationship between the two would be challenging but also very much worth it for them.
6 Power Girl
Power Girl is another woman who would take Nightwing out of his comfort zone but in a good way. Known for being boisterous, Power Girl is ridiculously powerful and would be a big help for Nightwing in a fight. On top of that, her tough exterior hides the heart of someone who will do anything for the people she loves and that's the kind of woman Dick needs in his life.
Nightwing would also be pretty good for Power Girl, as she's always looking for somewhere to belong and be loved. Nightwing is one of the most accepting and caring heroes in the business and his love would do wonders for Power Girl.
5 Harley Quinn
Harley Quinn and Nightwing are complete opposites in a lot of ways but opposites often attract. Quinn's wild spirit makes her a good match with someone that can ground her and the two of them would actually get along very well, as Harley has a tendency to love with complete abandon, something that Nightwing needs in his life.
Nightwing would also ground the chaotic Quinn while she added some missing spice to his life. The two would also be a formidable team in combat, as both of them have a smart, acrobatic fighting style that would go well together.
4 Raven
Raven and Nightwing have known each other for a very long time and their solid core of friendship would make for a great foundation for their relationship. The two of them could look out for each other, as Raven would be able to sense when Nightwing needed help and he could provide the rock she needs to help her with her own issues.
Together, the two of them would fill up a lot of holes the other has in their life, providing a loving relationship that grew from a place of friendship. Their vastly different upbringing would bring something new to each of their worlds, making them stronger than they are apart.
3 Catwoman
For Catwoman to leave Batman for Nightwing would be a controversial move and not one that Dick would probably go for, but he would be missing out. There are few women out there as caring or as understanding as her and Catwoman's inherent mental toughness makes her the perfect woman for someone like Nightwing. Their fighting skills are complimentary and they would make a great couple.
Beyond that, Catwoman deserves someone who could open up completely to her at all times and while Batman tries to do that, it's very hard for him. It wouldn't be hard for Nightwing and the two would have a great relationship that would make both of their lives better.
2 Donna Troy
Donna Troy and Dick Grayson grew up with each other on the Teen Titans and know each other better than just about anyone. They already love each other to a degree and for that to turn romantic would make sense and also be the best thing that could happen to both of them. Donna's fierce loyalty makes her a great match for Dick and they already have the beginnings of a great relationship.
Dick would bring a measure of stability to Donna's life and their love would be a logical growth of their friendship, giving to each other more than either had before. Their relationship would be very beneficial to both of them.
1 Starfire
Honestly, if Batgirl and Nightwing were to completely call it quits, there's only one other woman who Dick Grayson would choose—Starfire. The two of them have been on and off since their time together as Teen Titans and proved to be perfect for each other. The two of them ending up together at some point is pretty much a no brainer.
Dick and Kory have been in love with each other for years and while they may not always end up together, their love is strong enough to keep them close. There are few couples in the DC Universe with as storied and powerful a relationship as these two.