Longtime podcast producer Cecily Foster has always operated behind the scenes. For years, she’s worked toward hosting her own show, putting everything, including her love life, on the backburner. So when her boss finally offers her the chance, she’s over the moon. But there’s a catch. Actually, two 1) The show will be about Cecily’s dating life 2) Cecily will be mentored by renowned dating coach/life coach/influencer Eliza Cassidy. Cecily would rather do anything else than put her singledom on display, especially since the last time she mixed work with romance the outcome was catastrophic. But when Cecily’s boss tells her that doing the show is the only way to protect her mentee's job, she realizes she has no other choice. To make matters even more complicated, Cecily finds herself unable to stop thinking about Will, a photographer she serendipitously met while chasing a runaway dog down a busy street. Even though there are sparks between the two, Eliza forbids Cecily from dating Will, whom she believes is no better than Cecily's disappointing exes. As Cecily struggles to balance her real romantic life and the one Eliza wants to create for her, she finds herself at a crossroads. Will she fall back into old patterns, or is this her chance to finally find love that lasts?