The Bet Facilitator

Simon Gallagher is going to his 15 year high school reunion. Salutatorian, captain of the basketball team and well loved by his classmates, he was voted the most likely to succeed. But Simon has an embarrassing secret, he never lived up to the hype. To get out of a bad debt, he has entered into a bet with the class bully to kiss a woman he doesn't know before he returns home.
He has no hope of winning the bet, so he enlists the aide of Gwendolyn Chambers, who he has no idea, had a crush on him in high school.
She accepts the challenge to help him even though it will break her heart if he succeeds.
Yes, it's a 'Hallmark' styled script, but it's a little more edgey than that. It has all the drama and pathos, and yes, it has the usual 'Hallmark' ending, but it's written in a way that makes you laugh and cry, boo the villain and cheer for our heroes.
You all know how it ends, but it's the journey that makes this script so good and worth reading.