Jeri Ryan (Sherri)
On paper, Charlie and Sherri were the perfect couple. In fact, that’s one of the reasons why Charlie started dating her in the first place. He saw a lot of himself in her, but as it turned out, he wasn’t all that happy with what he saw. He eventually got tired of her games, so the two broke up.
Later on, Alan and Charlie run into Sherri while visiting the eye doctor. She and Alan apparently had a connection, so they started dating. However, similar to the countless other relationships in TAAHM, Sherri and Alan didn’t last long, and that was the end of that.