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.

Debbie shares relationship news, but Colt thinks she's moving too fast. Natalie reunites with Josh, but a sudden change of events turns her off. Tania wonders if Joel has baggage from his past. Things get steamy as Veronica and Justin take a weekend trip.

After his third date, Caesar must decide which woman he wants to pursue. Debbie visits Tony in Canada, but it's not what she expected. Natalie meets Josh's ex-wife and their teenage son. Veronica receives shocking news from Justin.

Caesar tells the matchmaker which date he's chosen. Debbie makes a decision about moving in with Tony. Natalie asks Josh if he's willing to have more children. Tiffany's son learns that she's dating again.

Debbie's friends question her decision to move in with Tony. Natalie reconnects with Mike. Tiffany loses faith in Fabian. Caesar and Alona say goodbye. Tania attends a party hoping to meet someone new.

Tony meets Colt, and Debbie tells him she's moving. Natalie returns to Sequim. Tania explores a romance with a woman. Caesar worries about Alona and their future together. Tiffany goes on a date with a new man.

Natalie opens up to Mike about why she left. Tiffany meets with Dan to tell him some unexpected news. Tania has an eye-opening conversation that motivates her to close the chapter on her marriage. Veronica reaches out to Tim for support.

Caesar makes contact with Alona. Debbie packs the rest of her belongings and heads to Canada with Tony. Tiffany reunites with Ronald in South Africa. Mike's mom confronts Natalie.

The 90 Day singles are back together for a no-holds-barred look at their successes and failures in love. Veronica is joined by a special guest, Tiffany has an update about her relationships, and Natalie faces a difficult choice.

After a shocking moment on stage, the 90 day singles return to dig even deeper into each other's love journeys. Caesar's love life gets crowded, Tania expands her horizons, and Debbie and Tony face off with Colt and Vanessa.