Brett and Olivia spend some time with Woody and Amani. Both Woody and Amani are skeptical of Brett and his intentions and ask him about when he bailed on the bachelor party.
Bennett talks to Amelia about his ex and what it was like living with her.
Christina is back to being rude and finely tells Henry that he needs more from him. He opens up a bit and tells her why he struggles being more assertive. He tells her that she needs to work on her patience.
Amelia brings up kids again, and Bennett feels that it's premature.
Miles tells Karen that he battles clinical depression and she has reservations about what that means and if he's masculine enough for her. She thinks it's a red flag
Brett and Olivia talk about money. He finds out that he makes three times less than her, and it may be an issue for her because she likes nice things and to do stuff and doesn't want him holding her back.
They also talk about sex and she's fine waiting whereas he's game for the sooner being better.
The more Brett and Olivia talk the more he picks up that she has a full life and it doesn't actually sound like she needs or wants him in it or that there is room for him or any relationship.
Olivia makes a faux pas and says that she's still single and alone, and it doesn't sound like he can bring any of himself to the relationship but she assures him that they both will have their own lives and then a life together.
The couples get together and ask about each other's relationshps and rating them. Brett refuses to rate because he thinks it's dehumanizing. He overhears Olivia rate him a seven.
Christina doesn't like that he didn't rate it, and she brings it up later when the two couples are together. Christina then tells Olivia that she's seeing red flags with Brett. Olivia says she's giving him the benefit of the doubt.
Bennett and Amelia continue to get closer. So do Amani and Woody who end up having sex.
Brett and Olivia butt heads when he stops communicating and shuts down on her.
Miles asks her about how she feels about his admission and about becoming physical, and she says that she doesn't plan on it.