Gerald vs. Jamie O is an episode in the Hey Arnold! TV Series.
Gerald and Arnold are walking to Gerald's house to see Gerald's new bike, but Jamie O has his bike. They're heading to Gerald's room, but Jamie O steals his room. Gerald says his new Pop Daddy T-shirt has come in, but Jamie O steals it. Gerald's tired of Jamie O bullying him and stealing his stuff.
Gerald wishes he had something that Jamie O couldn't take from him. Suddenly, he meets a girl named Chloe and falls in love with her. She asks if she can borrow a cup of sugar. Gerald likes her, even though she looks about 13. Gerald invites her over to his house, but she starts to fall for Jamie O. During one evening, Chloe tells Jamie O that she likes him. Jamie O says that he is not interested, but Chloe replies that she doesn't give up easily.
Jamie O tells Gerald that Chloe is only spending time with him so that she can get close to Jamie O, but Gerald doesn't believe it thinking that Jamie O just wants to take Chloe away from him like all of his other stuff. Chloe continues to visit Gerald and sneaks away to see Jamie O whenever Gerald has to leave the room. Gerald ends up walking in on Jamie O and Chloe numerous times and always suspects the worse despite not realizing what actually happened.
After seeing Jamie O pick up Chloe, who claimed to have hurt her ankle, he rushes over and tells him to put her down. Jaime O subsequently drops her on the ground, causing Gerald to begin trying to fight Jamie O, who refuses to fight as he believes it is stupid. After ripping Jamie O's shirt, Jamie O starts fighting seriously and Chloe breaks up the fight. Chloe confirms that she was just seeing Gerald so that she could spend time with Jamie O. Gerald gets depressed by the truth and runs into his room. Jamie O then goes to Gerald and gives back his Pop Daddy T-shirt, promising he'll be a better brother. In the afternoon, Gerald and Arnold are having some pie but Jamie O then grabs Gerald's pie, going back on his promise, prompting Gerald to chase him.
- Jazz Raycole guest stars as Chloe.
- The midget clowns and the two-headed sideshow made a cameo on a TV show on Gerald's television. They were first seen in Buses, Bikes, and Subways after Harold and Helga stole their bike.
- The video game Gerald is seen playing has the skyline of Chicago in the background.
- The number of fries on the plate does not decrease as Jaimie O eats them.
- After Jamie O gives Gerald his Pop Daddy T-shirt back, he speaks as he walks away, but his mouth is closed.
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