The men square off in a very physical game of street basketball, and are not afraid to slam one another to the ground if it means they will get some one-on-one time with Jen. As one team prevails, one special guy wins a romantic date with Jen to Harlem's Cotton Club, where the couple is serenaded with a special private performance by Lava Records' R&B/pop vocalist and actress Vanessa Williams. During the date, things get emotional as Jen's date breaks down about a past love. Then Jen steals away one of the guys on a helicopter ride to the Mohegan Sun Casino in Connecticut, where the stakes couldn't be any higher. Back at the house, the guys question Fabrice's interest in marriage, and jealousy about the individual dates begins to brew. The remaining six guys hang out with her in Central Park. Jen and the guys engage in a friendly game of football, and the guys struggle to find time to spend with her alone. Realizing that time is of the essence, one guy steals her away for a romantic walk, another takes her out on a rowboat and another sweeps her away for a cozy chat under a tree. At the rose ceremony, things start getting serious when Jen must send two of the eight men home.

Jen and her final four men leave New York, as Jen looks forward to meeting the guys' families in their hometowns. Jen gets to travel back to her own hometown, Chicago, to spend some quality time at Wendell's apartment before meeting his family. When Jen and Wendell arrive at his parents' home, she discovers that his family was so nervous, they had a few too many cocktails. Will that cost Wendell his relationship with Jen? In a totally different but dramatic trip, Jen also travels to Rochester, NY, and takes a journey with Jerry down memory lane, as they first visit his high school. This is Jerry's first time visiting his home in many years and, as if he weren't nervous enough about keeping his connection with Jen, he's also very anxious about Jen meeting his deaf mom and whether they'll be able to communicate. So Jerry decides to teach Jen a bit of sign language to ease the potentially awkward situation. Then, when they head off to dinner with his family, there's an unexpected power outage and Jen's entire experience with Jerry's family is lit by candlelight. Ryan takes Jen home to Medford, OR, to meet his folks. Not only does his mom, Barbara, whip up a batch of "Barbaritos" -- her own special recipe for burritos - but, in one of the strangest moments in "Bachelorette" history, Jen is asked to sign their bathroom wall. Will that odd request ruin Jen's impression of Ryan's parents? In Oklahoma City, John Paul hopes to impress Jen by taking her to meet his parents and having a chef from one of his restaurants cook them a romantic dinner at his place.