|First Appearance||The Sushi Connection|
He first appeared in "The Sushi Connection." Here, Caitlin Cooke had a crush on him. Jen, knowing nothing about him other than that he was a cute tennis player named Kyle, decided to get them together. While Caitlin often flubbed up in front of him, Jen was able to help her out when Caitlin accidentally whacked him with a tennis racket. When Kyle went down, Jen suggested that he and Caitlin go on a date, and Kyle woozily agreed.
Later on, he showed up at the Penalty Box to take Caitlin out. As they left, Jonesy and Wyatt came in. Soon thereafter, Jonesy realized that the boy in question was "Dirty Donaldson." Upon hearing who this was, Jen went into shock, and Wyatt was amazed, stating that he always thought "Dirty Donaldson" was just an urban legend. Jen soon went into crisis mode and sent Jonesy and Wyatt out to spy on the date.
For dinner, Kyle took her to Super Terrific Happy Sushi. Although Caitlin hates fish, she was unwilling to tell Kyle for fear of disappointing him. She ate a bite, and after not liking it accidentally ate some wasabi. Seeing her reaction, Kyle didn't help, instead choosing to laugh at her predicament. Eventually, Caitlin choked down the dinner, and Kyle took her out to a second surprise: the Vomit Comet. Here, Caitlin was able to say that she had a fear of rollercoasters, but Kyle decided to ride anyway. When a girl hit on him, however, Caitlin decided to ride.
Her taking this ride led to a crisis when her upset stomach combined with the twists and turns to make the rollercoaster live up to its name. To make things worse, she puked at the apex of a loop-de-loop, which meant that the whole coasterfull of people got caught in the vomit on the other side. After this, Kyle stormed off angrily, mad at her. Caitlin was initially unhappy, but Jonesy and Wyatt caught up to her, and Wyatt pointed out that Kyle didn't pay any attention to what she might want to do. At this, Caitlin realized that Kyle was indeed a jerk and immediately got over him.
Since then, Kyle has mainly been a background character. He appears in the very next episode at the end in a non-speaking cameo, where he falls into the new TushControl3000 Things That Beep gets at the end of the episode, which suggests that he falls in love with the chair in much the same way Jude did earlier on. He then appears in The Girls in the Band carrying a spotlight and commenting on Caitlin's poor performance. Kyle also shows up in The (Almost) Graduate as one of those hoping to get a job as a Greeter God at Albatross & Finch, and in Bring It On buying hockey tape (and, because of Jonesy, a stick). He also showed up in Club X-S in It's Always Courtney, Courtney, Courtney! looking at Jen when she was topless.