Jeri Ryan as Sherri | Then
Though Charlie had seemed to have gone through all kinds of women, Sherri was the kind of girl he never encountered before. She was a woman skilled at playing hard to get, constantly leading Charlie on into having sex with her.
But because he was considered the one being used, Charlie decided he wanted to seek revenge. This ultimately led to their downfall.
Brooke Shields as Danielle Stewart | Then
Danielle was the girl with a partying past. This didn’t seem to stop Charlie from setting her up with Alan. She ended up dating him, believing he would change for her, something she did not receive from her other boyfriends.
However, when she mentions to Charlie, “I’ve slept with a lot of guys and even a few women and even with couples”, he suddenly decides he wants to be with Danielle now. The brothers end up fighting over her, causing her to leave.
Brooke Shields as Danielle Stewart | Now
Brooke Shields was already a recognized actress and model before she had appeared on the show. Already receiving a lead role at the young age of 12, Brooke had continued on to book major roles in shows and films such as The Blue Lagoon, Endless Love, and a recurring role in NBC’s Law & Order: Special Victims Unit.
She also received two Golden Globe nominations for her performance on the NBC sitcom, Suddenly Susan.
Jeri Ryan as Sherri | Now
Jeri Ryan is a German-born American actress who is best known for her role on Star Trek: Voyager, for which she earned and won four nominations for a Saturn Award. She is also known for her performances on several television series such as Boston Public, Dark Skies, and Shark.
The talented actress is currently in the works for her next film, The Relic.
Kimberly Williams-Paisley as Gretchen Martin | Then
When Alan’s ex-girlfriend Lindsey eventually got engaged to another guy named Larry, Alan began dating his sister Gretchen. She becomes a recurring character in the show’s 11th season, keeping a relationship with who she thought was “Jeff Strongman”. This, apparently, was Alan’s alter-ego, an identity that Alan gets very into.
Eventually, Gretchen deciphered his lies and breaks up with him, telling him she already experienced all this dishonesty with her ex-husband.