Natalie meets up with Josh in LA; Caesar hires a Ukrainian matchmaker to help him find love in Kyiv; Debbie arranges to meet a new man while her ongoing drama with Colt resurfaces; Tania goes on her first date in Aruba.

Veronica goes on a first date that ends on an awkward note. Caesar has heavy competition at a meet and greet event. Debbie meets Tony for the first time. Natalie finds out more about Josh's past. Joel questions Tania's past.

Caesar attempts to make a meaningful connection at his meet and greet event; Debbie celebrates her 70th birthday alongside Tony; Natalie seeks advice from Josh's friends; after a second date with Justin, Veronica speaks to Tim about boundaries.