The season begins with a champagne toast between Hannah and The Bachelor castmates Demi Burnett and Katie Morton. Hannah greets the men at the mansion later that night. Connor S. jumps over the fence; John Paul Jones says his name three times; Joey presents a baby basket that contains wine to make a toast; Ryan rides on rollerskates; Jonathan presents a box of pizza via a mimicked proposal; Luke P. climbs up over the limousine to growl at Hannah; Cam, who already has his first impression rose from the season finale of The Bachelor, throws a bouquet of roses; Matt drives on a tractor; and Peter presents a wing pin.

Grant, Luke S., Mike, Jed, Jonathan, John Paul Jones, Dylan, and Luke P. attend the first group date of the season at Belasco Theater, headed by drag queens Alyssa Edwards and Alaska and runway coach J. Alexander, where they judge the Mr. Right pageant. With Chris as emcee, Mike walks around in heels and Jed sings a song with a guitar. Luke P. wins the Mr. Right pageant by declaring his love for Hannah. At the night portion, the men question Luke P.'s sincerity. Mike asks if Luke P. is just there to win. Jed receives the first group date rose.

Tyler G. takes the first one-on-one date of the season to the San Gabriel Mountains, where he and Hannah go racing on an ATV course. While they are cuddling on a couch, they discuss the pressure of having the first one-on-one, as Hannah did on Colton's season. At dinner, they talk about their futures and Tyler G. receives a rose.

Devin, Matteo, Daron, Connor J., Kevin, Dustin, Tyler C., Joey, Peter, and Garrett go on the week's second group date, where they travel to a warehouse for a roller derby judged by Chris Harrison and Fred Willard. At the after-party, Cam, who didn't have a date that week, crashes the party to see Hannah. Tyler C., Garrett, and Kevin confront Cam about interrupting their date. Dustin receives the group date rose.

Hannah cries at the cocktail party, saying it's "hard to make decisions." Kevin pulls her aside but is interrupted by Cam, carrying a box of chicken nuggets and inviting them for a "ceremony". Kevin calls Cam a control freak. Luke P. invites Hannah to a makeshift massage table and they kiss. Jed walks in on Hannah and a shirtless Luke P., embarrassing her. At the rose ceremony, Connor J., Daron, and Matthew are eliminated. Later, Luke P. approaches Hannah during her interview, and they

Prior to the start of the episode, Tyler G. had to leave the show when details of past inappropriate behavior emerged online.^[40]

Jonathan, Matteo, John Paul Jones, Kevin, Jed, Tyler C., Mike, and Cam are chosen for the first group date of the week. It is centered around reproduction and led by Jason Biggs and Jenny Mollen of The Try Guys. The men put on clothespin nipples to simulate breastfeeding, care for a fake baby, and sit for a labor simulator. At the night portion, Jed and Mike get one-on-one time, before Mike is interrupted by Cam on three separate occasions. Jonathan interrupts Cam to get "revenge". Mike receives the group date rose.

Connor S. receives the week's one-on-one date to go sailing. Hannah cancels because she is ill, but she invites him over instead. He leaves cute sticky note messages. Later that night, Connor S. receives a rose. They dance to a private concert starring Lukas Graham, where he sings "Love Someone".

Luke P., Dylan, Garrett, Grant, Peter, Joey, Luke S., and Devin go on the second group date, a photoshoot promoting The Secret Life of Pets 2 led by photographer Franco Lacosta. Franco pairs each man with a "pet model". Former contestant and Hannah's friend Demi Burnett hires a makeup artist and an animal handler to flirt with the contestants while Hannah views from hidden cameras. At the end of the photoshoot, Luke P. tries to "steal" Hannah but is turned down and told to "slow his roll." He interrupts two more one-on-ones and is turned down by Hannah both times. Peter receives the group date rose.

With fifteen contestants remaining, Chris Harrison announces the men will travel to Newport, Rhode Island. Jed receives the first one-on-one date to explore Boston, where they tour Quincy Market, take pictures in a photo booth, stop by for drinks and a kiss at Cheers, get ice cream at Halo Top Creamery, and finish at Auerbach Center, home of the Boston Celtics. They play with point guard Terry Rozier and shooting guard Jaylen Brown. At the dinner portion, Jed receives a rose.

Dylan, Matteo, John Paul Jones, Connor S., Garrett, Dustin, Devin, Grant, Peter, Kevin, Mike, Luke S., and Luke P. travel to Fort Adams to train with the Newport Rugby Club, splitting into a Blue and Green team to play in front of a crowd. At half time, the Blue team leads 0-5. Kevin dislocates his shoulder and is taken to the hospital. During the second half of the game, Luke P. picks up Luke S, slams him to the ground, and knees him in the head. Blue wins the game 7-10. Later, Luke P. tells Hannah that Luke S. swung at him and he acted in self-defense. He says that when Hannah is gone, Luke S. only speaks about his liquor company. Luke S. denies this, mentioning both Luke P.'s comments about going home and his issues with the other men. The other men support Luke S, and after Kevin returns (with an agnioclaviculous joint sprain), they confront Luke P. Garrett tells Hannah he is "crushing on [her] hard" and receives the group date rose.

On the second one-on-one date, Tyler C. comforts Hannah and they go fishing. Tyler receives the rose at the dinner portion of the date. They travel to the Jane Pickens Theater & Event Center for a public Jake Owen concert.

Continuing from the previous episode, Luke S. and Luke P. debate in front of Hannah. Hannah walks off from the conversation, leaving Chris Harrison to tell both Luke S. and Luke P. that the cocktail party is canceled and the rose ceremony is happening immediately. As Hannah starts the rose ceremony, Luke S. pulls Hannah aside, apologizes, and quits the competition. John Paul Jones and Matteo are eliminated.

The cast arrives at the Achnagairn Estate in Inverness, Scotland. They go to the Hootananny Ceilidh Bar and Hannah tells the men to "reset".

Hannah picks Mike to explore Scotland on a one-on-one date, where they explore the shop Books, Maps, and Prints, and try Black Death candy from Mr Simms' Olde Sweet Shoppe. They try whiskey and haggis. At dinner, Mike opens up about his ex and receives a rose.

Devin, Tyler, Jed, Dylan, Grant, Connor S., Dustin, Peter, Kevin, and Garret are chosen to go on the group date, where they will participate in old Scottish Highland games in front of a crowd. They train and put on kilts. The games include axe-throwing, yoke races, and Scottish blackhole wrestling. After everyone competes, Jed requests to get pinned by Hannah and wins the competition. Mike confronts Luke P. about what he will say on his upcoming one-on-one date back at the estate. At dinner, Jed has the first one-on-one time and Hannah reveals that they share one square foot of the land for winning the competition. Kevin walks in on Jed and Hannah kissing, which upsets him because he and Hannah have not kissed. Peter and Hannah play snooker and end up kissing on the snooker table. Back at the estate, Mike has left the room, so Luke P. receives the date card. Jed receives the group date rose.

The next morning, as Luke P. leaves for his one-on-one date, he attempts and fails to make small talk with the other men. Hannah and Luke start their date in a field of flowers. They talk on the side of Urquhart Castle overlooking Loch Ness about why the other contestants don't like Luke P. He admits that he "screwed up" but still thinks that Luke S. was there for the wrong reasons, that the other men "blow it up way out of proportion", and that "everybody loves him." Hannah calls him arrogant and tries to ask how the conflict makes him feel. He says it is unfair but it does not affect him emotionally. Hannah walks off in frustration, speaks to the crew, and tells Luke P. that she "needs more." She asks to know "the real stuff" and not what makes him look good. Hannah pauses the conversation and they go to view a castle. During an interview, Hannah states that she wants to send Luke P. home, but that she can't do it, even though she can't make excuses for him anymore. At dinner, Luke P. admits that he is trying to be perfect and that it is hard for him to let loose. He says he loves "every single thing" about Hannah, and she says that she is not perfect. Luke P. asks what his flaws are that Hannah doesn't like, but Hannah tells him to own up to them himself. Hannah questions how she feels.

Continuing from the previous episode in Scotland, Hannah sends Luke P. home. He walks away, returns shortly, and they fight. Eventually, off-screen, she allows him to stay. Mike says “It’s still the Luke P. show, homie. And it’s hella annoying.” The morning of the cocktail party, Luke P. goes to a church to pray.

At the cocktail party, Garrett grabs Hannah to ask if Luke P. brought up any other men during their date. Hannah says he did, but only because she asked. Connor S. walks in and steals Hannah away. Garrett confronts Luke P. about his conversation with Hannah. Luke P. tries to defend himself but is constantly interrupted by the other men. A loud argument breaks out, cutting off Connor S.'s one-on-one time. Hannah yells at the men. She leaves, but they continue arguing loudly. She returns, tells Luke P. to stop making excuses, and tells the other men to stop focusing on him. She leaves crying. Chris Harrison hugs and tries to reassure Hannah.

Hannah cancels the cocktail party and the episode cuts to the rose ceremony. Devin, Grant, and Kevin are eliminated. Hannah says she is angry at all the men, and immediately leaves for the night. The next morning, the show moves to Riga, Latvia as the content portion comes to a close and the interview portion of the episode begins. Chris interviews Hannah in Latvia. She says that she is trying to stay hopeful, that she feels like the show might have been a mistake, but that she won't end it early.

Eric Bigger, a contestant from the thirteenth season of The Bachelorette, and Nick Viall cameo in a commercial segment promoting Annabelle Comes Home.

The show opens in Riga, Latvia. The men explore the streets, eventually arriving at Pullman Riga Old Town Hotel. Garrett receives the first date, which makes Luke P. jealous. They meet in the forest, and it is revealed they are going naked bungee jumping from a cable car in Sigulda. Hank and another girl greet them, saying that naked bungee jumping is a tradition for couples in Latvia. After reluctantly going bungee jumping, Garrett reassures Hannah that his heart is in the process. Hannah says that the date was just the start of the week. At dinner, Garrett asks about Hannah's past, and she says she won't let fear control her. They both talk about trust and falling in love. Garrett confesses that he is falling in love, and Garrett receives the rose. We learn that only Peter will be excluded from the group date. Garrett describes his date to the other men, and Luke P. insults him and accuses him of lying.

The next morning, Hannah and the men explore Riga Central Market. They cheer with vodka, pickles, and cheese. Tyler C. gets Hannah flowers. Dylan and Tyler C. arm wrestle at a pub. On the subway, Hannah shares about her date with Garrett. Luke P. is frustrated it was true. Dinner begins with Tyler C. confessing he is falling in love with Hannah. Jed plays the piano for her. Luke P. compares being cheated on, which Hannah has, to the bungee jumping date. Hannah says it wasn't sexual. Tyler C. gets the group date rose.

The show moves to Amsterdam, Netherlands, and tensions are high with hometowns the next week. The contestants are at the Kurhaus Hotel in The Hague when the date card arrives. Hannah picks Jed for the first one-on-one of the episode. They explore the city, get chocolates and flowers, and go on a boat. They meet a couple who have been married for fifty-four years but dated for only ten days. At dinner, Hannah admits she is falling for multiple men. She says that knew that she was falling in love with Jed while they were dancing in the streets. Jed affirms that he is falling in love with Hannah, and she gives him a rose. We learn that Tyler C. will get the next one-on-one date.

On the date, Tyler C. and Hannah ride horses, which scares Tyler C. They struggle with the horses while exploring The Hague. They get ice cream after failing to get waffles. They then get pickled herrings, which Hannah reluctantly eats but likes. Tyler C. speaks about his and Hannah's missed opportunities, and Hannah pushes Tyler C. to open up about his experience on the show. Hannah wants Tyler C. not to hold back, and wants to know that both of them are "in this thing." At the dinner portion, Hannah pushes Tyler C. to open up about what is hard and scary. Tyler C. speaks about his parents' divorce and says he worries about failing at marriage. Hannah shares a similar sentiment about her parents' communication. Hannah gives Tyler C. a rose, and Tyler C. says that he is falling in love with Hannah. Back at the hotel, Mike receives the next one-on-one date, which makes Connor S. angry. Connor S. goes to Hannah, but she sends him home, saying she feels that there are stronger relationships.

The following morning, Mike and Hannah travel to Utrecht and bike around the city, leading to an artist. Hannah draws Mike, and Mike draws Hannah. Luta, the artist, asks Mike and Hannah to change into robes. She draws a portrait of them. Before dinner, Hannah contemplates about whether or not to continue with Mike. She sends him home, saying she does not think she can see a future with him. Back at the hotel, Tyler C. calls Luke P. a villain. A crew member comes in and takes Mike's bag, signifying to the other men that he was eliminated. The other men criticize Luke P.'s excitement that Mike was eliminated. Peter and Garrett are concerned about the three-on-one the following day.

The following day, Jed tells Luke P. not to worry about the other guys, saying to "keep [his] head out of [his] ass." Peter, Luke P. and Garrett travel to Gouda, Netherlands for the date. Luke P. grabs Hannah first. He talks about Jed's quote from earlier and Garrett being fake-nice. Hannah says in an interview that she is tired of the drama. Garrett talks to Hannah next, and Hannah mentions what Luke P. said about him, which they quickly resolve. Garrett tells Luke P. that he will be sent home, and they argue again. Luke P. screams at Garrett and angers Peter.

Hannah arrives in Westlake Village, California to meet Peter. They ride in Peter's sports car, where she finds a condom in the car's center console. They arrive at Peter's private plane. They fly, overlooking the entire view of the Bachelor Mansion. They go to his house, where Hannah meets Peter's parents and brother, and they share about their experiences on the show. They eat Cuban food and do a German prayer. Peter's brother talks to Hannah about Peter's past relationships, and Peter's parents compliment her.

The next stop is at Jupiter, Florida, where Hannah and Tyler get on a boat. Tyler drives the boat to show Hannah his hometown. Then, they jump into the water. Tyler points out his childhood home. They go to a beach bar and dance to reggae music. Tyler explains his dad's health concern. Hannah meets several of Tyler's relatives. Tyler's brother overhears his stories and Hannah sits down over with the brother. Tyler and his mom discuss whether he is ready to propose to Hannah. Tyler's dad expresses worry about Tyler being in love and getting his heart broken.

Hannah arrives in Gainesville, Georgia to meet Luke. They attend Sunday School in Oakwood's Court Cafeteria and meet several of his friends. Luke leads the bible study group. Hannah meets Luke's family. They question why Luke is still on the show if he has been having so many issues. Luke's father asks him if Hannah is worth it, and he says "a hundred percent" and that he loves Hannah. At the end of the date, Luke apologizes for the problems with the other men. Hannah says that she is falling in love with him.

At the park in Knoxville, Tennessee, Jed takes Hannah to a studio, andhey write a song together, with lyrics about their date in Boston. As they finish recording the song, Jed says he loves her. Jed brings Hannah to his family in Sevierville later that night, Jed's father talks about Jed's career while his mother talks to Hannah. Hannah sits down with Jed's sister, and she says Hannah will interfere with Jed's music career.

Hannah arrives in the Greek island of Crete as overnight dates have begun. Peter has the first date with Hannah, sailing on the Aegean Sea. Later that night in Agios Nikolaos, Peter opens up about his thoughts on a potential engagement, which ends with Hannah inviting him to the fantasy suite.

Tyler has the next date at a spa, reassures Hannah that his family approved of her, and gives her a massage. During the night portion, they talk about their relationship. Hannah expresses that although she does not want to be intimate with him, she would like to take the time in the fantasy suite to develop their emotional connection. Tyler accepts, and they spend the night in a houseboat.

Jed meets with Hannah in the town of Vrachasi in Lasithi to celebrate and dance with a Greek family. During the night portion, Jed expresses his concern to Hannah about Luke's behavior. Hannah becomes frustrated and tells Jed that her and Luke's relationship is wholly separate from theirs. At the end of the night, Hannah invites him to the fantasy suite, and Jed accepts.

Hannah feels unwell about her decision and asks to exit the limo on her way to the proposal ceremony. She slips and falls, and a producer asks if she can go through with the proposal. She says yes. Tyler exits the limo first, indicating that he will not receive the final rose. He begins to propose, but Hannah cuts him off to let him know he has not won. Tyler says he will always support her and departs. Jed shows up, and plays a song for his proposal, and she accepts. They share footage of their time being engaged. The day after their engagement, we learn that Jed warned Hannah that he had a casual fling before the show. This upset Hannah, but she accepted it.

A few weeks after filming ended, Hannah and Jed reunited in a safe house in Los Angeles, as news broke on Jed's serious relationship prior to the show. Jed tries to explain his side of the story, claiming that his relationship prior to the show "wasn't serious" despite telling her he loved her. Hannah removes her ring and tells Jed that this was not the engagement she accepted.