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Lyndsey Mc Elroy (Courtney Thorne-Smith) served as Alan's on/off love interest from season seven until the end of the series.At one point, she was even engaged to him, and lest we forget, she also had a – ahem – moment with his ex-wife Kandi in season 10.However, his relationship with Lyndsey was never celebrated nor good for him.You could probably say she was the worst love interest Alan had on the show.After the departure of Charlie Sheen from the show, there was a need for someone to pick up his wild and wacky mantle.It wasn't Ashton Kutcher's Walden who did so, but Amber Tamblyn's Jenny who was Charlie's long-lost illegitimate daughter.
In comparison to Charlie, Alan had fewer on-screen romances or potential suitors, so fans naturally cheered for him when he got his chance.
One of Charlie Sheen's last storylines on the show featured his character in a relationship with Chelsea (Jennifer Taylor).
While the committed life was utilized as a way to stir up the hedonist lifestyle, there was never a genuine spark between Charlie and Chelsea.
Jones was lightning in a bottle – and it made all the cast members and crew very rich in the process.
After a detailed and well-publicized break-up with Sheen, the show added Ashton Kutcher to the ranks and carried on for a few more seasons.
Eventually, his own insecurities and Kandi's realization that she could do better resulted in their marriage falling apart.