Overview
Tim and Cole head to Maryland to spend the weekend at Tiffany's. Tiffany has a surprising move to help get Tim back into the dating world, and Cole opens up about the struggles in his relationship with Jeniffer.
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8 - 1Dear Diary, This Is the New Me May 10, 2026 -
8 - 2Dear Diary, I'm Gonna Lose It May 17, 2026
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8 - 3Dear Diary, I Have a Big Secret May 24, 2026
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8 - 4Dear Diary, I Kissed My Best Friend May 31, 2026