Gear up for another rollercoaster ride of love and laughter as “90 Day: The Single Life” returns with Season 4 Episode 2, titled “Tyray’s First Date,” airing at 8:00 Pm on Monday, January 8, 2024, on TLC. The episode promises a mix of new connections, reunions, and a milestone moment for one of the singles.

Chantel ventures to an olive oil farm, opening the door to a potential love interest that could spice up her journey. Meanwhile, Natalie reunites with Josh to explore new living arrangements, adding a twist to her single life escapades. Veronica steps up as Tim’s wingwoman at a local singles event, turning up the charm to help him navigate the dating scene.

The spotlight, however, shines on Tyray as he embarks on his first-ever date, a momentous occasion that is sure to be filled with nerves, excitement, and the unpredictability that comes with diving into the world of romance.