He was one of Lorelai's first big love interests on Supernatural) as Rory's ex Dean.
Gilmore Girls debuted in 2000 and the original show lasted for seven seasons, though the final series is widely disliked by fans. This is because Sherman-Palladino departed as showrunner, and the heart that defined the show was lacking in the last series. Luckily, Netflix later funded a four-part miniseries dubbed Gilmore Girls: A Year In The Life, which caught up with the title duo and the show's many other fan-favorite characters years later, which included cameos from McCarthy, Padalecki, and Milo Ventimiglia.
One character who was noticeable absent from the Gilmore Girls reunion was Max Medina (Scott Cohen), Rory's old teacher who later romanced Lorelai. While their relationship got off to a mixed start, Max soon proved to be something of an inspirational figure for Rory. Max was an all-around good guy, which led to a romance between him and Lorelai, despite the conflict of interest. It was initially short-lived as Lorelai decided to break it off when the heaster threatened Max's job.
Even the break-up was short-lived as the two quickly started seeing each other again. Max eventually proposed to Lorelai on the Gilmore Girls season 1 finale - despite some love triangle business between them and Luke (Scott Patterson) - but she accepts. While on the surface Max is just about the perfect man, after a crazy bachelorette party Lorelai realizes one key issue with the impending marriage - she's not in love with him. She quickly breaks off the wedding, to the heartbreak of both Max and Rory.
Gilmore Girls kept the embers of a love story between them flickering for a little while longer, but by season 3 Max definitively wanted nothing more to do with Lorelai and the character left the show soon after. While there was discussion of Max making an appearance during Gilmore Girls: A Year In The Life, the showrunners couldn't find a good spot for him. If the show ever returns, maybe he'll make a comeback, but with Lorelai now married to Luke the odds of romance are slim.