Week five started with Webster taking back all of the choices he made regarding Benavidez. He explained that he was sending her back home because the whole situation was creating too much conflict between him and the other women.
Then, they had a rose ceremony where more women were sent home leaving twelve women left. After the rose ceremony, Webster announced that this week they will be traveling to Costa Rica.
Webster met all the women at the new mansion in Costa Rica and asked Sydney Hightower to accompany him on an individual date. They talked about their backgrounds and what has happened throughout their lives. Later on that night Hightower shared emotional stories about her childhood at dinner with Webster. This gave Webster more insight into who she is as a person. At the end of the date Webster gave Hightower the individual date rose.
The next day Webster and ten of the women headed to a waterfall for a group date. Webster planned a photoshoot for Cosmopolitan magazine where the best model would be featured on the cover of the magazine with Webster. Victoria Fuller was chosen as the best model in the end.
After the group date Kelsey Weier talked to Webster about her feelings towards him. She revealed that she is falling in love with him. After their talk, Tammy Ly brought to Webster’s attention that Weier had been very emotional throughout the whole dating process. This made Weier feel as if she needed to stick up for herself which ultimately led to more conflict.
Continuing on in week five, Kelley Flanagan went on an individual date with Webster. During the date Webster had feelings of concern regarding Flanagan not being able to open up to him. After talking through his concerns, Webster gave Flanagan the date rose.
The next morning Weier went to Webster’s house individually to talk to him about accusations being made about her at the mansion. Webster loved that Weier came over to talk to him and decided to give her a rose.
That night the women were planning to meet with Webster for a cocktail party and another rose ceremony; however, Chris Harrison announced that they would be going straight into the rose ceremony; giving none of the women a chance to speak with Webster before sending people home. This made many of the women upset at Weier because she got a chance to speak with him and no one else did.
As the rose ceremony was beginning two of the women took it upon themselves to talk to Webster. This upset some of the women that did not get any time with him that day. Two women, Shiann Lewis and Lexi Buchanan, did not receive roses and were sent home.
