Sports Agent Leah Nachman is knee deep in her sister's wedding drama and inches away from her biggest career goal when she runs into the high school boyfriend who broke her heart. The last thing she needs is another confrontation with the man too many people are convinced is her bashert. But perhaps he can be of use. After all, she's totally over him. Right? Sofer and Comic Letterer Samuel Levine is at a professional crossroads when he runs into what he believes is a fated second chance. He hasn't seen Leah in ages, but the guilt over how they broke up still eats at him. When Leah proposes a fake 'dating contract' to help her make partner at her agency, and thwart her sister's matchmaking, Samuel agrees. His goal is forgiveness, after all. But the more time they spend together as 'plus ones,' the more like fate the dates feel. Leah is convinced love and ambition can't co-exist and Samuel's convinced he's losing her. Will they let their dating contract expire or give love another chance?