While begining to succumb to peer pressure to lose her virginity, Holly J. expressed an interest in Blue as a possible candidate to have sex with her after, hearing from Chantay that he had a reputation for having had sex with many girls. While working together on a project alone in the art room, she throws herself at him, he rejected her advances for sex, but courted her for dates for the rest of Season 8. This initial courtship came to an end after Holly J. lied to him about not wanting to go to an expensive concert with him, as she was not able to afford a ticket, and afterwards when she trashed Mia Jones's reputation on television. They reconciled in the Season 8 finale at a school dance, after Holly J. was held at gunpoint, even though Holly J. also had feelings for Spinner Mason at the time. She permanently ended their relationship after getting frustrated with him due to the fact Blue kept trying to turn her into his ideal woman.
Season 8In Didn't We Almost Have It All, after hearing that Anya may have lost her virginity to Sav Bhandari, Holly J. feels insecure about being the only virgin on the Power Squad so she decides to lose her virginity to Blue Chessex.
In Art class, she partners with Blue and decides to stay after school and work on the project alone. Holly J. attempts to seduce Blue, but Blue rejects her. When alone again, Blue now wants to have sex with Holly J., but she rejects him, just like he rejected her, since she now knows she's not the only virgin on the squad. The two laugh and begin a relationship.In Money for Nothing, Holly J.'s family is going through financial troubles (because her dad "made some risky investments", according to her mother), so her mom cuts her credit card in half. This means she can't go on the $350 cheerleading trip to Florida, and on a date with Blue to a $125 concert. She doesn't want Blue and her teammates to know about her problem, so she lies to her teammates about going to a family wedding and tells Blue that she really didn't want to go with him, making him upset. Holly J.'s jealousy towards Mia reached the peak when she tells a news reporter about Mia's secret, and it's aired on the news. The Power Squad does not like Holly J.'s actions and they vote her off of Power Squad. She then tries to rekindle her date with Blue, who rejects her by calling her spoiled and selfish.
In Up Where We Belong, Holly J. becomes discouraged in herself when she can't ace her next art assignment. When Blue earns an A+ on his assignment, Holly J. states that it isn't fair because she tried just as hard as him, and received a C. In recognition of her hard work the teacher allows Holly J to have a second chance and repeat the assignment, however Holly J. simply copies an artists' work and thus her grade doesn't change. Holly J. is determined to keep her grades high and confronts Blue for help. Blue tells her that art is something you can't try to do. It's something you just do. He tells her that art is from the heart, not the head. The next day, Holly J. goes to art and earns an A+ like Blue did because it was a "Holly J. Original". He is happy because he knew that she could do it, and he is happy that Holly J. finally has some more certainty in herself. Blue continues to get straight A's in art class.
In Danger Zone, Blue asks Holly J. to the Black & White Dance, and as much as she wants to say yes to his offer, she rejects, knowing that she might have a thing for her co-worker, Spinner. As they are about to close The Dot, a former Lakehurst student comes in with a gun and holds them at gunpoint. During the robbery, Blue shows up to The Dot and Holly J. answers, too scared for words. The door is foggy, so she writes the word gun on the door. Then Blue leaves. Blue ends up calling the police, and they arrive surrounding the vicinity of The Dot. Holly J. ends up going to the dance, and everyone applauds her for being brave and getting the shooter to exit The Dot. She gives him an apology and dances with Blue and they move their relationship to being more than just friends.
Season 9In Just Can't Get Enough, Blue and Holly J. are happy with their relationship until Blue begins to annoy her. He tries to help her with her presidency, but only ends up coming off as controlling. She tells him she can't and won't change who she is for him, and he tells her goodbye, ending the relationship.
In Wanna Be Startin' Somethin', Blue makes a comment to Holly J., "There is no I in team" to which Holly J. replies, "There is in bite me!"
In If Jay Can't Be Happy..., Holly J. and Blue had been talking about rap music, as Blue was studying it in his music theory class. When the dust affects Holly J., she begins to rap to Blue: "Yo, my name is Holly J. / and you gots to be told / when it gets into the winter months, it starts to get cold / but luckily for everyone, you will not shed a tear / 'cause coming round the corner is some holiday cheer / gotta be hardcore, hardcore, hardcore / when you're standing under mistletoe that hangs above the door / do I have to make this clear / should I write it in a note? / just put your arms around me / stick your tongue into my throat / booyah". As she raps, the entire cafe stares at her, while Spinner and Jay are dying from laughter. Blue calls Holly J.'s rap "cute", but quickly leaves The Dot. However, he later comes back and is waiting for Holly J. outside of the cafe, as announced by K.C. and Clare.
- First Relationship:
- Second Relationship:
- Blue was the only person who called Holly J. "Holly."
- Although a season 8 promo implied that Holly J. and Alli Bhandari would compete for Blue's affections, this didn't end up happening.
- They never had sex, despite Holly J.'s initial attempts to lose her virginity to him.
- Both of them go by different names: Holly J.'s real name is Holly Jeanette but, prefers to be called "Holly J.", and Blue's real name is Bradley but, prefers to be called "Blue".
- Their first kiss was in a classroom while working for an art project in Didn't We Almost Have It All.
- Beat It (1) and Beat It (2) are the only episodes in which Blue appeared but Holly J. did not.