Michelle landed the first date, taking him bike riding and introducing him to her students via video chat. She told Matt her parents were hesitant for her to join the show because she had to put her life on hold, but they agreed to support her no matter what. Michelle revealed she would say yes if Matt proposed and she thought he was The One, while he said he would move to Minnesota for her.
Rachael, for her part, organized a skydiving date because trust is a big factor for her in relationships. However, things took a turn when she slammed into the ground upon landing. Matt ran over to check on her and confessed that he didn’t realize how strongly he felt for her until watching her get hurt. She cried over his admission and was appreciative of his concern for her. She later told her mom that makeup was covering the injuries to her face.
Rachael’s family — specifically her dad — was skeptical about the fast process, but she hoped Matt would ask for her father’s blessing. She admitted she was in love with him and noted she would accept a proposal. Ultimately, she was let down when Matt opted not to ask for permission to pop the question. He didn’t want to do it with all four families, but he promised to call Rachael’s dad closer to time if the opportunity arose.
Bri and Matt went off-roading in a Jeep during their date. He wanted to move past their level of comfort with each other, but she was scared to tell him she was falling in love with him. Matt believed he and Bri had a special connection, and although she wanted to put up a wall, she told him about her feelings.
Serena P., meanwhile, introduced Matt to her Canadian culture. He then met her family, who expressed their doubts that she was ready to get engaged. Serena’s anxieties deepened about making a mistake with Matt since she had hoped her hometown date would help her become more confident about taking the next step.
Matt felt something was off with Serena, so he confronted her before the rose ceremony. He told her he intentionally spent more time with her than the other women to build their connection. She thought she was afraid of her feelings for him, but she realized he was not her person. Matt was shocked and disappointed, but he wanted Serena to be happy. She chose to leave, which made Matt worry that the remaining women might do the same.
At the rose ceremony, Matt encouraged Bri, Rachael and Michelle to be sure they were ready for an engagement before accepting a rose. They all decided to stay and received roses.
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