Alex is the business partner of an old friend of Sookie's, Joe Mastoni, that Lorelai and Sookie run into at the Learning Center after taking a course on how to run an inn. Alex and his friend Joe are looking into opening a chain of coffee shops. While Sookie and Joe reminisce about old times Lorelai and Alex hit it off resulting in him calling her at the end of the episode to ask her on a date to try different types of coffee.
On that date, Alex says he has two kids, a daughter and son, aged 6 and 9, whose mother he is not with anymore. He is also a big fan of the outdoors and upon Lorelai seeming to take an interest, he invites her to go fishing with him, which despite her lack of experience she accepts. Luke teaches her to fish. Though Lorelai doesn't tell him, Alex senses she has never fished before and as such takes her to the Shehela Lodge and Spa afterwards.
Alex later acquires 4 tickets to see the musical Levittown in New York and invites Sookie and Jackson to join them. The musical is a bust, but the four of them have a good time anyway. Alex is shown to be kind and considerate to Lorelai and her eccentricities. He is mentioned a few times during the rest of the season when Lorelai runs into Max again and feelings resurface for him, she is said to still be dating Alex though we never see him and when or what exactly caused their break up is unclear.