They dated twelve years ago. Because of an anonymous dating app, they’re about to unknowingly date each other again. Timini Jensen doesn’t think there’s a point to dating. Relationships drag people down. After all, nobody runs faster when they’re in a three-legged race, right? Plus, there’s the part where she seems to pick guys who are only pretty on the outside. When a friend asks her to test a new dating app his company made that doesn’t allow users to see pictures of potential matches, she tries it out. Since it’s all anonymous and she’s not even looking for someone to date, it’s harmless. Except she really connects with a guy she’s been messaging—Jackson. He’s sweet. And great to chat with. The fact that he’s her opposite makes their conversations that much funnier and more interesting. And she’s about to find out that he is actually her high school ex-boyfriend, Jack Oliver. The guy whose personality flipped when his family’s business suddenly started doing extremely well. The guy who ripped her heart out. Now she doesn’t know if she can trust that he’s the sweet, funny Jackson she has gotten to know so well through messages, or if he’s the too-good-for-everyone Jack she remembers from high school. All she knows is that chances are good that she is not going to fall for her ex.