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.

Caesar goes on his first date in years. As Debbie and Tony make their relationship official, Debbie's living situation takes an unexpected turn. Natalie has a blowout fight with Josh. Tiffany rekindles things with an old flame.