Winnie works at a demanding and uninspiring job as a writer, but she dreams of having her own column. In her free time, she goes on quite a few dates and has a blog under the pseudonym Luckless, where she writes about all her failed dates. When she writes about a failed date with the sports manager Holden, it goes viral, and her boss catches wind of it. Suddenly, she gets the opportunity to have a column, but she has to continue dating Holden and blog about it…
"Despite the warning bell of Up Faith & Family as the publisher, this movie is actually quite funny and good.
