The next day, Shawntel leaves for her date, saying she knows she has a strong connection with Brad and hopes he wants to continue this journey with her. They greet with a kiss that is definitely more one-sided on her part. They hop on some bikes and ride through the town as Brad says his relationship with Shawntel has been "slow and steady." They stop at a farmer's market and drink coconut milk straight from the coconut. Brad appreciates that Shawntel doesn't take herself seriously, shown by her free spirit as she jumps rope and plays dominoes with the locals. They meet a vibrant lady named Aunty B. who asks if they're in love. Brad's awkward non-answer tells the whole story. Aunty B. tells them to "hold hands and maybe kiss sometimes." It's as good advice as I've ever heard. Shawntel realizes that she could be falling in love with Brad and resolves to tell him.
They sit down for a picnic in the middle of a goat field, which doesn't sound like the most appetizing venue to me, but whatevs. Brad tells Shawntel he likes that he doesn't have to put on an act around her because their chemistry is so natural. Shawntel confesses that she's only ever told two guys she loved them, then tells Brad she's falling in love with him. What does the kiss of death sound like? "That means a lot to me, it really does," quoth Womack. And yet he can't stop thinking about his date with Emily. He says tonight's date with Shawntel needs to be big so that he'll have clarity about his feelings for Shawntel.
That night, Brad says he needs to figure out his feelings for Shawntel and where they're going. They sit down for a candlelit dinner as he plies her with lies about how much he loved their day. She tells him again that she's falling in love with him. Again, he doesn't reciprocate. Shawntel says she wants Brad to come to her home so he can meet her mother, then asks about his. He shares that his mother is huge in his life because his parents split when he was four years old, and his father was never part of his life. He thinks it's significant that he can share these things with her because he normally keeps them bottled up inside. He says that this comfort and openness is what he's looking for in a wife. Brad tells Shawntel all the things he loves about her as she gives him the hard sell for her hometown, saying, "You'll fall in love." He responds coyly, "Maybe I already am." Clearly not, buddy. If you were, you'd just damn say it. It begins pouring rain. Brad grabs Shawntel's hand, and they kiss like so many bullshit stories about the power of love. Shawntel says it's her most romantic day ever, but Brad reveals he still has another surprise in store: A concert by Anguilla's most famous singer, Bankie Banx. Not that they hear any of it because they're too busy making out and mooning at each other.