When Rose—Ryan’s college best friend and unrequited love—crashes his wedding with a change of heart, years of buried emotions threaten to shatter his world. As Ryan reels, his best man must navigate a minefield of secrets to get his friend to "I do" before the past rewrites the future.

After inheriting her late grandfather's old winter home one week before Christmas, a young woman discovers that he may have hidden a winning lottery ticket somewhere in the house.

It follows Amanda as she volunteers to lead a company launch party. She's partnered with seemingly arrogant Sam, but she's unaware that he is also the man she's been flirting with in an anonymous chatroom.