Now on the verge of engagement to his longtime girlfriend, Kiera, Dan McPherson finds himself aching again for his wilder days. After a bitter fight, Kiera reluctantly agrees to a month apart to let Dan "figure everything out." But after a chance meeting with a mystical old woman, Dan awakens to find himself in an existence where his now much different life has progressed exactly as it would have had he never met Kiera. Dan dives into his new reality with gusto, only to realize that what he truly wants, he has had all along. Now he must try and win Kiera's heart all over again from scratch, starting with the first awkward hello to a woman who has never met him, yet he has known for years.