90 Day: The Single Life

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.

Ceasar goes on his first date in years, and Tiffany rekindles 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.

Caesar has to decide which of his three dates to pursue; Debbie is shocked when she goes to visit Tony in Canada; Natalie meets Josh's ex-wife and son; Justin shares shocking news with Veronica.

Caesar reveals which date he's decided on; Debbie comes to a decision about whether or not to move in with Tony; Natalie and Josh discuss having more children; Tiffany's son finds out that she's dating again.

Debbie's decision to move in with Tony gets questioned by all of her friends; Natalie and Mike reconnect; Tiffany loses confidence in Fabian; Caesar and Alona call it quits; Taina tries to meet someone new by going to a party.

Tony meets up with Colt and Debbie tells him she's moving; Natalie comes back to Sequim; Tania tries out romance with a woman; Caesar has his doubts about Alona; Tiffany goes on a new date.

Natalie tells Mike why she left; Tiffany shares unexpected news with Dan; Tania has an enlightening conversation that inspires her to change; Veronica looks to Tim for help and 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.

Debbie and Colt continue their big fight; the various men in Natalie's life meet face-to-face; Veronica introduces her new lover; Tania and Syngin finally get closure.