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Kyle learns the true meaning of "Boston Pride" when he visits Kristen's hometown. Kristen treats Kyle to some of her favorite local spots ranging from a North End Italian deli to a Southie bar straight out of Good Will Hunting.
Kristen and Kyle travel to the weird, wild and wacky city of Portland. The pair gets down and dirty as they dig for clams with a local top chef, share beers with a bestselling author, and hit a Tikki bar with a rock star.