It's time for Kirk's date, and he dresses up in his finest flannel to start his fairy tale outing. Ali explains (to us, not Kirk, because she's not ready for that level of emotional honesty) that she is very distracted and has a lot on her mind. Kirk thinks everything is fine and dandy and he is in sweet, mold-free love with Ali. A horse-drawn carriage pulls up outside the twosome's lunch spot and they hop in and ride to YET ANOTHER medieval castle. Seriously, if you don't like castles, don't go to Portugal because THAT IS ALL THEY HAVE. Ali's distraction does not stop her from making out with Kirk, just a little. Kirk tries to be understanding as Ali is fretting over which of her five suitors is most likely to not humiliate her on a public stage. Kirk tries to comfort her by pointing out that he hasn't brought someone home to meet his parents in, like, three years, and that woman was a physical therapist sent by the hospital to move his arms every three hours. Ali does not look reassured.
Later, the couple is dining atop the abandoned castle. Ali has added a white blazer to her ensemble to make sure things stay business casual. Kirk has also gussied up and donned his country club finest: a yellow button-up and blazer. Ali apologizes to Kirk for being so distracted earlier. Kirk wants her to be able to talk to him about her feelings and shit, at least on paper and definitely not during the Olympics or really any sporting match, but in theory: Emotions rule! Kirk then pinky-swears that he is falling in love with Actual Ali, not Idea of Ali or Idea of Love or Bachelorette-Induced Drama. They make out and then get serenaded by an over-tanned woman in a serape with a flower behind her ear and voice of a eunuch. They make out some more, because what the fuck. Just make out with everyone Ali, no one is judging! No, really! Maybe a little.
Ali heads out to her last date, which is with Chris. She is just dating him "like a friend" because she frequently dates her friends? I don't really know what she means by that. Like, you can't date EVERYONE. Leave some for the rest of us, woman! For some reason the producers think it would be an awesome idea to put Chris and Ali on a scooter and set them free to roam the countryside around Lisbon. Chris drives like a girl so Ali has to take over the reins. This does not bode well for moving past the friendship stage of the relationship. Ali parks the scooter and starts grilling Chris AGAIN about his dead mother. I mean who feels romantically inclined when always being forced to discuss the recently deceased? So Chris and Ali don't make out in the shadow of Chris' mom, but fear not! The date's not over yet, even though Ali keeps telling the confessional cam that it might be a little too late for the Romance. So Ali takes Chris to a winery, because nothing spells romance like drunkenness. Over glasses of vinho, Chris explains that he just moves a little slower on dates and really likes the way things have been progressing with Ali. He would be so excited to bring her home to meet his family, because she would fit in and everyone would like her. Then Chris tells her that he had a present made by the family jeweler just for her. He didn't want to give it to her earlier, but now that he knows her and likes her, he wants to give it to her. So he gives her a tennis bracelet that is just like the one his dead mom wore and his sister wears. Word of advice, Chris: QUIT TALKING ABOUT YOUR DEAD MOM. Ali doesn't mind, though, and she and Chris roll around in the grass and kiss.