Although this movie was originally released in July, it takes place in February. The movie refers to the previous movie Signed, Sealed, Delivered: From the Heart, set during Valentine's Day, and in fact picks up the day after the previous movie on February 16th, 2 days after Valentine's Day, and the day after Oliver and Shane's date at Montaldo's. Given that it is February, and that the setting is in Denver, it would be very cold. When everyone is gathered outside Curly Dudley's home, everyone is wearing a jacket, sweater, or coat, except Rita. Rita is wearing a short, sleeveless dress meant for spring or summer. She would have been freezing.