Cupid's arrow hit Caleb's heart at an early age, linking him to Millie, the girl he's loved since kindergarten. But when Millie breaks up with him three weeks before high school graduation and marries someone else, Caleb's heart is ripped to pieces.

Caleb swears off long-term relationships and plans to remain a confirmed bachelor. While he's happy to date, he no longer has marriage on his bucket list. He's content with his life, but it suddenly veers off course when not one but two women—his ex and his next—cross his path, threatening his peace and throwing him for a loop. One of them is Millie, a recent and available widow. The other the infamous Jolene.

Caleb faces three paths—secure bachelorhood, a new woman, or an old flame. He can continue to play it safe, and if he does, nothing changes. But if he plays with fire, he risks burning his bridges. Can he take the leap into love or keep the status quo?