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Jesse hopes his online romance turns into real life chemistry, but Jeniffer has a secret. Natalie explores the Florida single scene. Ed has a new look but struggles with the past. Steph hopes to finally break her celibacy. Debbie joins a dating app.
Natalie and Debbie head out on first dates. Syngin and Tania struggle to leave their sexual relationship behind. Ed's date gets awkward after he cries at dinner. Jeniffer finally meets long distance love Jesse, but the passion isn't what she expected.
Syngin and Tania break the news of their split to her family. Steph overshares on a first date. Jesse's rudeness on their first date leaves Jeniffer disappointed. Natalie hasn't told Johnny she's still married. Debbie's blind date leaves her in tears.
Jesse meets Jeniffer's young daughter. Syngin gets back into dating by downloading an app. Ed jumps in fast on another international connection. Natalie has a second date with Johnny. Stephanie makes a move on her stylist.
Ed travels to Mexico to meet Kaory, but their date comes to a scary end. Jesse meets Cacua, but he's taken aback when Jeniffer confesses their history. Debbie heads out on a first date after a full makeover. Syngin comes clean to Tania.
Jesse learns the truth about Jeniffer and Cacua. Ed wants to speed things up with Kaory. Tania and Syngin have a tearful goodbye. Debbie worries that her date is uninterested. Natalie shares the truth behind her dating fears.
Ed contemplates making a move during his second date with Kaory. Jeniffers mom in concerned about Jesse's future plans. Stephanie ends up in the bath with an ex-boyfriend. Debbie fears she's being catfished.
After driving cross-country, Syngin meets a new love interest. Jesse and Jeniffer start to doubt their future together on an island getaway. Stephanie gets intimate with Fred. Debbie uncovers the truth about Jay. Ed attempts to impress Kaory's family.
Ed confesses to Kaory that he's looking for marriage. Natalie shuts down after learning about Josh's past. Jesse attempts to fix things with Jeniffer, but she tells him to leave. Debbie and Colt fight, and she worries she's being catfished.
Syngin goes on his first date since separating from Tania. Debbie and Colt make amends. Jeniffer and Jesse want one more talk with Cacua. Ed's trip to Mexico comes to an unexpected end.
Ed loses an old friend and reconnects with a past love. Jesse and Jeniffer discuss their future as he leaves Colombia. Debbie meets her date. Natalie gets honest with Josh.
The 90 Day singles come together to discuss life on the rebound. Debbie gets blindsided by Colt. Ed defends his engagement to Liz. Syngin comes face-to-face with Tania. Stephanie shares a celibacy update, and Jesse and Jeniffer defend their relationship.
The Tell continues with the cast ganging up on Jesse for his arrogance. Tania's mom has a lot to say about the relationship with Syngin, who gets caught red-handed. Natalie faces Mike, and the reality of another divorce proves too much to handle.
The singles are back to tell even more in a special final hour of The Single Life Tell All. Syngin relives his last night with Tania. Jesse is accused of gaslighting. Debbie gives Jay a piece of her mind. Ed's fiancee and ex come face-to-face.
