Nate Wright has had 4 ex-girlfriends (5 if you count Abby Wilson.) in the past. Ruby Dinsmore's status with Nate is unknown, as she has only been seen in Big Nate Blasts Off, the last novel in the Big Nate book series, which was released in 2016. Also unknown is the status of the unidentified girl in the current Comic Strip arc, as she has only said one line so far, from which we can not assume anything big about her or her relationship with Nate.
Abby Wilson was Nate's 1st girlfriend. He spent 5 minutes and 10 seconds exactly going steady with her before being dumped by her. Nate gave her his glossy which was returned back to him by Abby’s friend. This is the shortest relationship Nate has had in the Big Nate series and in the novels.
Angie was Nate's second girlfriend. They met because Nate's grades were so low that he had to go to summer school. There, he met Angie, and they became a couple. Angie was Nate's girlfriend from 1997 to early 1998. However, Angie breaks up with Nate, and ten seconds later, she's going out with Dan Labreque. She is mentioned later when Nate takes Jenny Jenkins to the dance. Nate could've have gotten Angie back after Angie and Dan have their first argument, but instead helps bring the two back together.
Kelly was Nate's 3rd girlfriend. She appears in The Complete Big Nate #11-12. They first meet when Nate goes to soccer camp. They soon become a couple. This is also when Coach John is introduced. Soon, Jenny is available. Nate breaks up with Kelly at the back of a detention slip in The Complete Big Nate #12. Kelly made a huge "scene" at P.S. 38 when she found Nate broke up with her with a detention slip.
Trudy was Nate's 4th girlfriend. She appears in Big Nate: Hug It Out!, Big Nate: Blow The Roof Off, & Big Nate: The Gerbil Ate My Homework. Lincoln Peirce released the strip in 2015. One day at the fair, Nate wants to ride the Flamethrower. He meets this cute girl who he rides the ride with. She then disappears. She was known then as "the mystery girl." It turns out, she moves to P.S. 38, and she's in seventh grade. The two met by running into each other in the hallway. They become a couple, but Nate breaks up with her because she takes up too much of his time and won’t spend time with his friends.
Some people think that the girl on the top right of page 153 in Big Nate In the Zone is Trudy. That can't be true, however, as the book was made before Trudy was a character in Big Nate.
Daisy was Nate's 5th girlfriend. Nate and Daisy met after Daisy noticed Nate's valentine card. They went on a date to the movies. They were supposed to watch Kong: Skull Island but Daisy had changed her mind. She dislikes cheez doodles because they are “too intense” for her. Nate hated the movie Daisy picked and fell asleep. Both of them decided that they had no feelings for each other and broke up. They only dated for a month. Nate said to Chad Applewhite that he didn’t have the “tingles” while dating her. Daisy also mentioned that “When we kissed I felt dead inside!”
Ruby Dinsmore is Nate's seventh and (likely) current girlfriend in the novels. Her only appearance was in Big Nate Blasts Off. Both Nate and Randy Betancourt had liked Ruby at that time. There was a big war. While it is not known who Ruby likes better, it is probably Nate. However, she never appears in the comics. It is unknown whether Nate and Ruby are still going steady because the last Big Nate novel was released 5 years ago in 201
The Unidentified Girl was first seen on June 21, 2021, talking to Nate on the beach. At this moment, not much is known about her, as she has only said one line so far.
Nate has had crushes on many girls in the past, including these three.
Unidentified Leader of Jefferson Posse
Unidentified Leader of Jefferson Posse, appeared in Big Nate: Goes For Broke, which is her only appearance. She decided to play a little prank on Nate when he was at Jefferson by writing P.S. 38 STINKS! on his cast.
Nate has had a crush on Jenny Jenkins since her debut (December 9, 1991), but when he was about to ask her out Arthur came, and Jenny fell in love with him.
Vanessa De Vries
In the 1999 summer chess camp arc (July 1–28), he met Vanessa De Vries (AKA “The Brain”), and fell in love with her while playing a game of chess against her. Nate had lost the match to Vanessa De Vries because he had a crush on her and couldn’t focus. and after that, she appeared in 2001's biggest chess tournament yet arc (January 1–13) and this time, Nate beat her at chess since she bet with Nate that she would go out with him if he won. This was cancelled since the tournament had a no betting rule, and Vanessa hasn't appeared since then. It was right after he broke up with Kelly.