Kyle Donaldson

Kyle Donaldson (also known as "Dirty Donaldson") is a teenage tennis player. He is not only a player at tennis, but also with girls; according to Jonesy, Kyle once dated five different girls in one summer (consisting of four cheerleaders and the coach's daughter). When Jen realizes who Kyle is, she recalls how all the girls at a soccer camp she once attended knew about Kyle (and his reputation) and notes that he wasn't even allowed on the grounds.

He first appeared in "The Sushi Connection." Caitlin had a crush on him, and 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.

He was first seen by Jonesy and Wyatt when he arrived at the Penalty Box to take Caitlin out. As they left, Jonesy realized that Caitlin's date was "Dirty Donaldson," a teenage tennis player legendary for his promiscuity. Upon hearing this, Jen went into shock, and Wyatt was amazed, stating that he always thought "Dirty Donaldson" was 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 hot girl hit on him, Caitlin decided to ride in order to make sure Kyle didn't get away from her.

On the ride, though, she soon proved that the Vomit Comet was aptly named, as the combination of fish and a wild ride led to her throwing up. To make things worse, she puked at the apex of a loop-de-loop, which meant that the whole coaster full of people got caught in a shower of her vomit. 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 at Albatross & Finch as a Greeter God, 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; there, it was never explained how he got into the club despite being a teenager, although it can be assumed that he possesses a fake ID.