I Dare You to Love Me - The Dare Duology

It's senior year. He rules the school. She just wants to make it to graduation. With prom only six weeks away, and his reputation at stake - will Brian be able to get "Scary Pants" out on a date?Brian Royland is the golden boy of Palm Beach High. He's smart, handsome, athletic, and charming. He could get any girl in school - but he procrastinated and is now dateless for the most important dance of the year.
When he hears about Iris Newman, aka "Scary Pants", Brian is intrigued. But when Brian's friends doubt he'll succeed in scoring her as his prom date, bets start flying, and she turns into a prize to be won. Iris has set several goals for herself; make sure her older sister has a smooth pregnancy, help her recently single mother support and manage their family, and find a way to stop her band's bass guitarist from asking her out every week.
She doesn't have the time or the energy to deal with the arrogant and pesky Brian Royland, who is suddenly determined to get her out on a date. It only takes six weeks for them to realize they have both experienced great loss. In the midst of family trouble and high school drama - could they be the key to each other's healing?