- „Sometimes you want something so bad you don't care about the consequences”
- —Caleb, to Annie[src]
An easygoing surfer who is passionate about community service, he is currently a student at seminary school studying to become a Catholic priest.
Caleb meets Annie at the beach. Caleb tells her he wants to talk to her about her foundation over coffee. On their coffee date, he tells Annie that he does charity work because he lost someone close to him and he made a promise that anytime he could do something, at the end Annie discovers that Caleb is a Priest.
In Blue Ivy, Ivy tells Caleb on the beach she doesn’t want to talk about Raj's death. Caleb suggests that’s how Raj’s family wanted to say goodbye and tells her about different wakes he went to. He then asks her about a beach wake and suggests they do that. After, everyone goes around talking about how much Raj taught them.
Caleb asks her how she’s doing while they’re at the beach and she tells him she’s going to do what she wants to do. She then runs across the street in traffic.Caleb goes to see Annie and asks for her help with his next fundraiser. Annie says she’s busy with all the wedding stuff. Caleb asks her if she’s alright and Annie says she doesn’t need to talk, and needs to stop being distracted. He shows up to the engagement party with a back up gift, since Annie forgot to get Naomi one. The gift is South Sea black pearls, which Annie then gives back. Annie admits to Caleb that she’s falling in love with him. Caleb reacts by leaving.Caleb later finds Ivy at the beach while it’s dark and stormy. Ivy tells him she’s going to go surf and Caleb tries to stop her. Ivy tells him he has no idea what she’s going through Caleb comes back, admits he hasn’t been honest to Annie, and kisses her in the rain.
Annie and Caleb planned a date in the park today to avoid temptation while on their date, they run into a nun that Caleb knows. Caleb tells Annie he has to make a decision. Caleb later goes over to Annie’s to apologize for putting her through his decision nightmare. After he talks about how Annie’s making him confused, he goes in to kiss her. Annie asks if he’s sure, and Caleb says he’s not and he doesn’t care about the consequences. The two then kiss and we next see them in bed. Later, Austin comes by and asks Annie to talk to Ade for him and convince him he’s a good guy. Annie’s apprehensive and tells him that his can of worms includes her, and that she doesn’t want everyone to know she used to be a prostitute. She then heads to the staircase and sees Caleb. That, of course, means Caleb heard everything. The next day Caleb quit the seminary because he felt he wasn’t worth of the cloth. Annie later finds Caleb drinking at Liam’s bar. Annie tells him she knows he quit because of her. Caleb tells her he quit because he’s weak, and that they both made mistakes and need to deal with the consequences. Liam brings Caleb to Max’s bachelor party later that night Annie finds Caleb at a church, and tells him he has to forgive himself.