After spending a week in Russell's world of mansions and political fundraisers, Jess realizes that Russell has never spent time at the loft, in her world. She invites him over for a weekend which starts with a creative American history/Candyland themed drinking game the gang created called True American. Afterwards, in an attempt to bond with the guys, Russell excludes Jess from their conversation which makes her angry. The next morning, Russell is grumpy, hungover, and uninterested in Jess' weekend plans for them. It all goes south when Nick accidentally stabs Russell in the hand with his smarthphone invention "Real Apps".
Later that day, Jess meets Russell at his house and they two continue their fight only to quickly make up and agree to try and spend equal amounts of time in each other's worlds.
Winston lands a job with a popular radio sports talk show, but his boss is difficult and demanding. He almost quits, but Elvin convinces him to stick it out and Winston eventually wins over his boss.