Shira Barbanel has a plan: this Hanukkah, she’s going to get a boyfriend. And she has the perfect candidate in mind—her great-uncle’s assistant, Isaac. He’s reliable, brilliant, and of course, super hot. The only problem? Shira’s an absolute disaster when it comes to flirting. Enter Tyler Nelson, Shira’s nemesis-slash-former-crush. As much as she hates to admit it, Tyler is the most charming and popular guy she knows. Which means he’s the perfect person to teach her how to win Isaac over. When Shira and Tyler get snowed in together at Golden Doors, they strike a deal—flirting lessons for Shira in exchange for career connections for Tyler. But as Shira starts to see the sweet, funny boy beneath Tyler’s playboy exterior, she realizes she actually likes hanging out with him. And that wasn’t part of the plan. Amidst a whirl of snowy adventures, hot chocolate, and candlelight, Shira must learn to trust her heart to discover if the romance she planned is really the one that will make her happiest.