Lorelai and Max meet at a Chilton Parent Night and instantly find affinity for one another, Max clearly smitten with Lorelai. After deliberating whether or not Rory will be too affected by their dating, they start a whirlwind romance, which ends when Lorelai gets scared of getting serious with Max.
News also spread at Chilton and Max decides to take a break to think. Lorelai seeks him out again and they start up slowly, culminating in Max' impromptu proposal, which Lorelai accepts. Though set to wed in late summer, Lorelai leaves town with Rory to avoid the wedding, effectively ending the relationship.
She bumps into Max about a year later and a short while after they share a kiss, but nothing comes of it.