In her first appearance in Season Two's "Haven't I Slept With You Somewhere Before?," it was revealed that Elaine had a sexual tryst with Hayden Fox five years prior to the episode's events. The tryst occurred in Miami (at the Blue Lagoon Motel), and it ended badly for both of them. Not wanting to get in a committed relationship with Elaine, Hayden left her without calling, with the excuse being that he needed to get ice.
Elaine became a villainess obsessed with getting revenge on Hayden for dumping her, and it was in the aforementioned episode that Elaine was hired as the President of Minnesota State University. Elaine's first act as President was actually firing Hayden, but after Hayden reluctantly threatens to publicly reveal the reasons for his firing, Elaine recants. Two episodes later in "Professor Doolittle," Elaine orders Hayden to teach a class on ancient history, knowing he hasn't taught a class in over a decade--even though it's part of his job description. Elaine insisted that it was not payback for Miami, despite describing every detail by memory. At episode's end, after nearly all of Hayden's class passes, Elaine wants him teaching more classes, and this time, she does admit that she's doing it for payback, boldly boasting that she is a spiteful and vindictive woman.
In Season Three's "The Day That Moses Came to Town," the evil Elaine confronted Hayden over running NBA legend Rick Barry away from the university while posing as Athletic Director Howard Burleigh, but that didn't deter her from her plan to make basketball a more prominent sport at the school, by attempting to bring in high-level coach Terrance Moses. To add slight insult to injury, Elaine ordered Hayden to recruit Moses himself, with Howard going along to keep an eye on him. Elaine's last appearance came later in the season in "The Iceman Goeth," when she approaches Hayden (who is still down over his break-up with Christine) at the Touchdown Club. After venting about their failed relationships, the two engage in another attempted tryst, and like their past one, it ended in the same fashion: with Hayden leaving her. An enraged Elaine crashes into Hayden's office holding an axe, but Hayden manages to calm her down. Elaine notices how broken up Hayden is over his relationship, and actually takes joy in seeing that he's "even more screwed up than she is."
- Elaine is mostly portrayed as a bit of a tyrant, especially where Hayden was concerned.
- Despite her intelligence, Elaine is also portrayed as damaged and prone to fits of anger, hence Hayden's nickname: "The Loon From the Blue Lagoon."
- Elaine's biggest personality trait is her obsession with revenge. Hayden referred to Elaine as "a wicked, spiteful woman with a nice set of wheels."
- Robin Strasser later appeared on a two-part episode of Dear John as the villainous Brooke Collins.
- Elaine Tewksbury bears some similarity to scorned villainess Ursula Gibbs from Psych, as both women were dumped after one-night stands and used their respective positions to get revenge on their former lovers. One difference is that Ursula wanted revenge because she was dumped and her former lover was in a new relationship. Elaine's motivation was solely due to being dumped.