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Al’s struggles with relationships have been a long-running plot point all through the series. In season one, Al dated Greta Post, whom he met whereas she was volunteering to help out throughout a Tool Time show. Al then showed a short interest in Jill’s friend Karen, whom he met at an impromptu gathering at the Taylor home, but Karen had already accepted a date with another House & Home Improvement News one of Tim’s friends. Next, Al went on one date with Tim’s ex-girlfriend Stacey Lewis, but had no real interest in seeing her once more. From seasons three through 5, Al went out with Dr. Ilene Markham, an orthodontist and the sister of one of Jill’s co-workers.