A shy writer takes over a popular advice column, and falls for a lonely widower who wrote to her seeking tips on diving back into the dating pool. When Katie Miner (Kellie Martin) took over the "Dear Viola" column, it seemed like a perfect fit. Katie has always been timid, but the opportunity to help others anonymously seems to bring out the best in her. When Katie receives a moving inquiry from a widower named Russ (Jefferson Brown) who signs his letter "Mr. Lost Love", she encourages him to get out and start dating again. Later, as their correspondences start turning personal, "Mr. Lost Love" finds a beautiful new girlfriend, and Katie realizes she's fallen in love. Meanwhile, as the relationship starts to turn serious, Katie realizes her only hope for winning Russ' heart is to finally stop hiding behind her "Dear Viola" persona. Now if Katie can just find the inner strength to overcome her crippling shyness, she may finally have a shot at true love with the man of her dreams.