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.

90 Day: The Single Life

Until We Meet Again

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.

Now or Never

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.

Fishing for the Truth

Debbie shares relationship news, but Colt thinks she's moving too fast; Natalie reunites with Josh; Tania wonders if Joel has baggage from his past; things get steamy as Veronica and Justin take a weekend trip.

Sorry, Not Sorry

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.

Old Flames and New Names

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.

What Happens in Vegas

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.

Make Me a Match

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.

To Bae or Not To Bae

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Colt's declaration about Debbie confuses Kenny and Armando.

Pillow Talk: Tell All Part 2

Tania and Syngin completely stun the Pillow Talkers with a "Tell All" first.

Pillow Talk: Tell All Part 3

Kenny and Armando, Emily and Kobe, Robert and Anny, Molly and Kelly, and even some exes are watching along, and no one is holding back.

Pillow Talk: Tell All Part 1

Kenny and Armando, Patrick and John, Robert and Anny, Kalani and Kolini and even some exes are watching along. No one is holding back.

Pillow Talk: I Was Here Waiting

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Now single, the favorites are looking to find love again while attempting to let go of baggage from their past; they must navigate the world of online dating, set-ups and first dates and learn to become exclusive with someone new.

S3 | Pillow Talk: I Was Here Waiting