|Relationship||Serena (broken up twice)|
|First Appearance||The Big Sickie|
Chad is initially regarded by Wyatt as competition, as he was Serena's boyfriend before Wyatt came on the scene. Wyatt realized it was not something to fear after Chad showed how unintelligent he was, and Wyatt earnestly thought about asking Serena out. He did this in "The (Almost) Graduate", taking Serena's heart away from Chad.
Serena went back to Chad in "The One with the Text Message", however; there, she broke up with Wyatt, saying she needed somebody more mature (although Chad's arguably--and ironically--way less mature than Wyatt is). This angered Wyatt, and he got fired because his jealously called out both Serena and Chad over the intercom.
Chad was once again important in the episode "Midnight Madness". Although he made no onscreen appearances, he was a large influence offscreen. There, Serena was angry at him because Chad had gotten only one ticket for a concert and planned to go there instead of spending New Year's with her. Because Serena didn't want to be alone and had heard that Jonesy was throwing a party, she came on to Wyatt again (through tears and assertions that she didn't like Chad that much anymore). While at the party, though, she got a call from Chad. Chad had decided not to go to the concert, as Serena meant more to him then the band that was playing. Serena as a result left the party, breaking Wyatt's heart again.
Since "Midnight Madness", both he and Serena have decreased in importance as characters. Their relationship changes again in "Kylie Smylie". There, Serena dumps Chad once again, and tries getting back together with Wyatt, who refuses to, citing that he no longer has feelings for Serena and has since moved on, and tells Serena to do the same.
- Chad is very laid-back–Wyatt even once described him as being "so chill he has permanent brain freeze."
- Even Chad had felt it was low that Serena broke up with Wyatt in a text message and felt bad for him.