For a brief period, she dated David Flair (both on-screen and off), who was already involved in an on-screen relationship with Daffney.This led to Keibler's in-ring debut at the Bash at the Beach in a Wedding Gown match, which she lost after she removed her own gown.After months of build-up, Keibler finally left Test for Steiner on the June 2 edition of Raw.

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On January 11, 2010, Keibler appeared as "the hot bartender", a new conquest for Barney, in the How I Met Your Mother 100th episode, "Girls Versus Suits".

On February 3, 2010, Keibler appeared on an episode of the USA Network show "Psych".

She was offered a beer, which she politely refused. She took over the 2004 Raw Diva Search for a few weeks, which led to several tag matches against the heel gimmicks of Gail Kim, Trish Stratus, and Molly Holly and with partners Nidia and the face gimmick of Victoria.

However, at the urging of Austin, she took a sip of the Miller Lite. Keibler also competed in the first-ever Fulfill your Fantasy Diva Battle Royal for the WWE Women's Championship at Taboo Tuesday along with Victoria, Nidia, Gail Kim, Molly Holly, Jazz, and then-champion Stratus.

When Orton challenged The Undertaker to a match at Wrestle Mania 21, Orton ended the relationship by hitting Stacy with an RKO, incapacitating her.

He justified it by claiming he was demonstrating how ruthless he could be in order to defeat The Undertaker.

In late 1999, Keibler entered a contest held by World Championship Wrestling (WCW) to find a new member of the Nitro Girls dance troupe.

It was also during this period that she began using what would become her trademark ring entrance: slowly putting her forty-two inch legs through the second tier of ropes, pausing to let the crowd momentarily see her panties.

During this time, she began an on-screen rivalry with former ally Torrie Wilson after Wilson left The Alliance, with Keibler ordering The Dudley Boyz to put Torrie through a table, and taking great pleasure in her evil actions.

Torrie, however, got her revenge after giving Keibler a wedgie then pantsing her on an episode of Smack Down! A key storyline for Keibler's on-screen character occurred when she left Smack Down! Keibler made her official Raw debut on August 12, 2002.

When WCW was purchased by the World Wrestling Federation (WWF) in 2001, Keibler's contract was bought by the WWF. She made her WWF television debut on the June 14, 2001 episode of Smack Down!