And then Robby the bartender and Jillian practice flipping a shaker for what feels like five hours, and Jillian drops the damn thing eighty times, and I really hope that thing gets disinfected before it serves any more drinks. Jillian says she loves Robby's fresh approach to life, and I guess "fresh approach" means "pretending to be Tom Cruise in Cocktail."
So they take their drinks and go out into an observation car so Jillian's car can fly all over the place, and they seem to be enjoying themselves, and Robby's fairly confident that he's getting a rose, and he offers one of those ridiculous over-qualified statements like "I think I'm in a position where I could quite possibly begin the process of considering falling in love" type of deals, and then the train goes into a tunnel, and we all know what that symbolizes.
Speaking of symbolism, the two of them go right for the caboose, which is where they're going to have dinner, and Jillian tells us that when she's with Robby, she feels "five or ten years younger," which is great, because that would mean that she would almost be his age, and then Robby says his dad "couldn't be happier" about his son being on this show, and everyone in his family thinks he's going to be the first to get married, because apparently all his siblings suffer from a family curse that involves not getting married, and then Jillian talks about starting a family in the next few years, and then Robby.... I don't know, he says about "putting yourself out there" and then he admits to being young and being "between jobs" but that's OK, because love has no age and has no job. Has no brain either, apparently.
Then they go downstairs in the caboose for dessert, and Jillian tells us that she doesn't think Robby's really considered where he's going to live and how to pay the bills and what a family looks like. "I need him to picture that before I can trust him and trust putting my life in his hands."
So after a commercial break, this date is STILL going on, and Jillian is talking about Robby making her feel "young again," like who are you, old Rose from Titanic? So then they lounge on a couch with all kinds of cushions, and they lie there and cuddle and Robby talks about how nervous he is, and he looks at the rose sitting there on a table, taunting him.