17 year old Nikita Singh is your average teenager. She's had her share of boy problems. Actually, maybe more than others. She's just about sworn off boys, that is until her grandma comes to town and ruins everything. She introduces Niki to a boy. The boy is annoying and self centred. But what happens when Niki makes a bet with the boy? "First one to fall in love loses."

Sameer Behl is probably the guy you see strolling down the halls, all cool like that, and you find yourself thinking, "Dang. He is SO hot...but he'll never be mine." He has a truckload of friends, a near-celebrity status, and a sexy violet-eyed girlfriend with possesive issues. He's who all the girls want and who all the boys want to be. Simran Singh is that girl you see strolling down the halls, dancing and and skipping around like a lunatic, and you find yourself thinking "What the hell is wrong with her? Well, she's hot." She's a "nobody" in school with one best friend. She can throw a punch like Muhammad Ali and serve in tennis like Rafael Nadal. Her only hope to be with her true love, Sameer, is her freakishly popular brother, Shahid. Of course Sameer and Simran fall in love...but will it last through all the irritating obstacles in life? Or will their delicate relationship fall apart?

Madison Truffles is your average nerd in high school. Her life is going smooth as a baby’s bottom except for the fact that her mother was murdered when she was five, her father is rarely at home in their luxurious condominium, and that she murdered Mac Bagels. With no need for any extra money, Madison still chose to work a part-time job at the Sweet Tooth Bakery owned by the old man, Mr. B, who was like a father to her. Although Madison was devastated when the old man died, he comes through with his promise. A promise that Madison forgot about until it came inside the bakery in a Gucci black subtle stripe wool blend two-button suit and a pair of blue piercing orbs to drool for.

Chase Evans may be a notorious playboy, but he’s always known he’d fall hopelessly in love one day. So when he meets Spanish beauty LaCienega [Lah-cie-Ena-ga] Perez and falls head over, he knows for sure she’s what he’s always been waiting for. Except LaCienega is already engaged by the time he meets her and to none other than his childhood best friend Jace Waite who Chase hasn’t seen since high school graduation. Meanwhile, he meets Krislynn Reimer who has a strange attraction for bad boys and imperfection. She's not interested in the pretty boys who are complete jerks like he is. She wants the real bad boys, the ones with addiction problems, family problems, money problems, woman problems, any problems! It’s her favourite hobby to take them home and put a Band-Aid over their hearts and nurse them back to health. Except when they make a full recovery, they always abandon her and always in the cruellest ways. The two utterly can't stand each other so how in the world did Chase end up as Krislynn's boyfriend and how in the world did Krislynn end up as Chase's maid?