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10 Boyfriends Of One Tree Hill Ranked From Worst To Best

One Tree Hill had its fair share of horrible relationships as well as a few great ones. Many of the main characters such as Brooke and Peyton had multiple boyfriends throughout the series, and some of them were much better than others. While none of the characters on the show were perfect, there were a few of them that mostly did the right thing and were good at heart.

We’ve put a list together of 10 of the most well-known boyfriends from One Tree Hill and ranked them from worst to best.

RELATED: Gilmore Girls: Lorelai's Boyfriends, Ranked


Dan Scott is without a doubt the worst character on the show. He started out as a bad father to Lucas and a manipulative man, but ended up being a murderer and literally a villain.

RELATED: 15 Famous Actors You Forgot Appeared On One Tree Hill

Before he murdered his own brother, Dan dated Karen back when they were in high school. He abandoned her when she got pregnant with Lucas and was dating Deb just a few months later and got her pregnant with Nathan. He was truly the worst boyfriend, and character, on the entire show. Even though the show tries to give him somewhat of a redemption arc at the end, it was hard to take seriously.


Nick Chavez is near the bottom of this list because he literally dated Brooke when she was a high schooler. This is a common but unfortunate trope from many teen dramas, but it’s very gross as well as criminal.

RELATED: Myers-Briggs® Personality Types Of One Tree Hill Characters

When Nick found out Brooke was his student, he kept dating her anyway. On top of that, he also was cheating on her. He was a horrible boyfriend because he was dating a minor which is never excusable, and abusing his position as a teacher.


Felix and his sister Anna were on the show in season 2. He started dating Brooke in this season which caused him to become one of Lucas’ rivals. When rumors were circulating that his sister Anna was gay, he wrote the word “dyke” on Peyton’s locker to remove suspicion from his sister. This is a pretty horrible thing to do and not a good way to confront the homophobic rumors. Instead, this just contributed to homophobia and showed the kind of person that Felix was. After finding out about what he did, Brooke dumped him.


Chris Keller was used on the show as a way to create drama between Haley and Nathan. Haley and Chris went on tour together, and they eventually kissed. While they were never exactly quite boyfriend and girlfriend, they were close and nearly dated a couple of times.

RELATED: 16 Character Additions That Hurt One Tree Hill (And 9 That Saved It)

Chris wasn’t the worst boyfriend on the show, and he did help Haley achieve some of her dreams. But, he was also rather conniving and often went against Haley’s feelings and desires to save her marriage so he could get what he wanted.


Lucas might at first have seemed like the better Scott brother, but he wasn't always the best boyfriend. While, in the end, he and Peyton end up together and have a good life together, in earlier seasons of the show he wasn’t always a good boyfriend to either Peyton or Brooke. In season one, he cheats on Brooke with Peyton. Then, again, he kisses Peyton during the school shooting while he was supposed to be in love with Peyton at the time. Overall, Lucas wasn’t very good at honesty, and his repeated brushes with cheating put him lower on this list.


Nathan was fair from a perfect boyfriend or character in the show, and he definitely had his moments where he wasn’t a great boyfriend such as when he becomes angry and an alcoholic in season 5.

RELATED: One Tree Hill: The 6 Best (& 4 Worst) Couples

But, overall, he and Haley have a strong relationship, and they always work things out and through with each other. While not the best boyfriend, he was definitely not the worst, and he and Haley definitely loved each other and found a way to make it work.


One of the most notable guest stars on the show was Pete Wentz from Fall Out Boy. Pete and Peyton briefly date in season three after they meet when Fall Out Boy performs at Tric. Their relationship isn’t very long, but while it lasts he is a good boyfriend. He even sends Peyton a plane ticket so she can come to visit him, but she uses it to see her ex-boyfriend, Jake, instead... proving that Peter was a much better boyfriend to her than she was to him. (That is, if we ignore the fact that Peyton was still in high school, and they shouldn’t have been dating at all.)


Julian doesn’t start out as a very likable character on the show, and there is a lot of drama with him at first when it’s revealed he used to date Peyton and is using Lucas’ novel to be around her again.

RELATED: 25 Mistakes Fans Completely Missed In One Tree Hill

However, in the end, he and Brooke get together, and they realize they are right for each other and get married. They end up having two sons together and mostly living happily ever after. Overall, Julian is a decent boyfriend and a good husband and father, giving him a higher spot on this list.


Jake was definitely one of the sweetest characters on the show and a good person. He was on the basketball team but never treated people badly like many of the other boys did. He was a single parent to Jenny, and he was very devoted to her. Jake and Peyton dated off and on through the first few seasons of the show, but drama with Jake’s ex, Nikki, kept them apart. Jake was a wonderful father and a kind person, and he always treated Peyton well. It’s a shame he wasn’t on the show more because he was one of the best boyfriends.


Keith Scott was nothing like his brother Dan. He was a caring and good person who was good friends with Karen and helped her as she was raising Lucas alone. Eventually, he and Karen officially start dating, and he is a great boyfriend to her. Sadly, they never get married as he is killed by Dan in season three. Dan was a wonderful partner and person, and he deserved better than what happened to him.

NEXT: 7 Casting Decisions That Hurt One Tree Hill (And 13 That Saved It)

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