Local minor league baseball players The Iron Pigs stop by the bar, and one in particular, Tommy, takes a liking to Chelsea. Meanwhile, the bar battles out where their baseball loyalties lie. Chelsea was born and raised a die-hard Red Sox fan; any mention of the Yankees sends her reeling. No surprise here, Nikki is a Yankees fan.
Two weeks in, Chelsea and Tommy are still dating. Rick comments that, for Chelsea, that's like two years. Tommy breaks the news that his team's going on the road for three weeks, which sends Chelsea into a surprising funk. She and Tommy just started dating, and she's not the type to tie herself down. Despite that, she brings up the issue with Tommy, who feels the same way. The two agree to be exclusive while he's out of town.
Meanwhile, Nikki recruits Rick to accompany her to visit her grandma Tess in the hospital. Rick, still clearly smitten with Nikki, has a hard time saying no. Rick has a way with old ladies and hopes that his charisma can win him a spot in Nikki's heart. But while at the hospital, Nikki and Rick run into her doctor ex-fiance. Seeing her with her grandmother, he assumes that Nikki has turned a new leaf and takes her aside for a chat. Seeing Nikki and her ex together, Rick can't help but feel heartbroken.
Tommy comes to Chelsea with great news... he's not going on the road anymore because he got drafted to the majors! There's just one problem... his new team is The Yankees! Chelsea hides her complete disgust, determined to do her best to support Tommy. The jersey doesn't make the man, right? She quietly agrees to go to Tommy's first game, showing support for her man in a Yankees jacket.
Chelsea and Dee Dee find themselves with the Yankee fans at the Yankee vs. Red Sox game, and Chelsea does her best to keep a low profile. But she can't help but show her true Red Sox nature and gets thrown out after she gets into a tussle with a Yankee fan.
Chelsea and Tommy have a heart-to-heart, and Chelsea admits that she'll never be able to support him as long as he plays for the Yankees. Tommy understands but tells Chelsea he needs a girl who will stand behind him in his career. The two amicably part ways.