As Holly narrates, numerous weddings are shown. What they all have in common, besides the fact Holly is never the bride, is her Great Aunt Lillian, who matched up each couple. Holly tells what she is looking for in a man, but the men shown with her don't seem ideal.In a small town, Holly works in her father's business, Castaway Fly Fishing. She hopes her brother Spencer will return and take over, since she has been running it since her father's death. She seems to enjoy it, but it's not really what she wants. The family has another business, the Holly Lane Christmas tree farm which is about to open for the season.Spencer is marrying Angela before Christmas, and an engagement party is being held. Although the leaves are still on the trees, many Christmas decorations are up. Spencer shows up with his college roommate Chris, who for some reason thinks he will not be welcome. A misbehaving boy drops a rose near the door to the house where the party is being held. Holly is standing nearby as Chris and Spencer walk in. In slow motion with elegant music, Chris hands Holly the rose.Cheryl and others think Holly needs a man. Holly walks outside where Chris is. He is uncomfortable with crowds and has a conversation with Holly which is not unpleasant, but he's not that nice and doesn't care to socialize. When both of them are back inside, Lillian is asked to pick another couple. She picks Holly and Chris. This makes them both uncomfortable.Back at home, Holly has an uncomfortable breakfast with her mother, Spencer and Chris.Angela tries on an old-fashioned wedding gown that Holly's mother wore but shows Holly what she wishes she could wear. Holly, who is planning the wedding, says that one is too expensive, and she persuades Angela to wear the one that they already have.At the Christmas tree farm, people are having a good time, buying trees and other merchandise, and having their pictures taken. Kids get their pictures taken with Santa Claus. Holly is hiding because she's embarrassed that everyone who went to that party knows Aunt Lillian put her together with Chris and will expect them to be a couple. Angela is helping out with the business and she gets Holly to come out of hiding and announces Holly will be her maid of honor. This makes Holly very happy until Spencer walks in and says Chris will be her best man.The wedding will take place at Cheryl's house so a visit takes place to plan exactly what will take place. Cheryl's book club, consisting primarily of older women, is meeting. The women persuade Chris to join them. He is uncomfortable. Eventually, Chris and Holly end up under the mistletoe and everyone says they have to kiss. Holly says it's all right. Just kiss her on the cheek. Chris angrily refuses to do anything.Back at home, Chris is helping Holly's mother with cooking. He's really good at that. Then there is an unpleasant meal where the family learns all about Chris. He is from Dallas but most recently lived in Chicago. His degree is in marketing and statistical analysis but he was recently fired from a great job. He will not spend Christmas with his family because they are not an ideal family like this one. In fact, he dislikes the holiday. Holly can't imagine anyone hating Christmas because she absolutely loves it.Spencer will not take over either of the family businesses. He plans to start a painting business. Holly was depending on money from the tree farm to pay for a trip to the Eastern United States.Back at the Christmas tree farm, Chris believes he can help improve the marketing of the business. He suggests changes to the web site, including better photos, but the photos others take aren't as good as they could be. Chris starts taking photos with his camera. He seems to be enjoying himself at last, and he has fun with the family. And he's really good at photography, but it's a career with too much uncertainty, so he won't listen to those who try to get him to do that as a career.The family decorates their own tree and invites Chris, looking serious at his laptop, to help. Once again, he seems happy.Later, Chris helps Holly with more decorations. His mother calls on his cell phone, and later texts, but he refuses to respond until Holly persuades him to at least make an effort. Chris finally agrees but tells Holly his family did not get along and his mother thinks Christmas with her family is a lot better than it really is.At the fishing business, Holly sees her ex and hides from him. Chris sees her and they talk about their relationships. Chris had a girlfriend but they broke up. Holly won't admit the other man was her boyfriend because they didn't date that many times and he didn't want to commit. Chris thinks it shouldn't take that long to figure out whether a man is worth having a relationship with.Chris and Holly eventually have a conversation where they learn more about each other. Holly loves Christmas because her father did. Holly had to quit college when her father died in a wreck that seriously injured her mother. Spencer was also in college but someone had to take care of their mother. Holly also had to run the fishing business and has been doing it ever since. It's not what she really wants, she says. Chris says Holly shouldn't do what other people want her to do. Chris says photography was his dream but he chose a major that would make him money and give him stability. As they make cookies together they have fun and end up getting flour and frosting all over each other.When Holly decides to take Chris' advice, her mother says maybe it's time to sell the fishing business and she knows someone who would like to buy it. Spencer isn't happy that other family members don't want him to do what he wants, and Holly thinks she will feel guilty if Spencer fails at what he wants to do because of her. Holly plans to go on her trip in the short term before deciding what she will do with her life. Some think she should plan weddings for a living.Chris gets a phone call. The company he was working for admits they were wrong to fire him and they want him back. Chris wants to return but wonders if he really should.The wedding is the next day and Holly has planned a surprise bachelorette party. But she has finally agreed to a formal date with Chris. She tries to do both at once. Wearing a sparkly and very short red dress, she and Angela go somewhere for what Angela believes will be an quiet dinner with just the two of them. It is anything but quiet as they walk into a room with the other bridesmaids who are quite loud and ready to party. There is plenty of drinking.Holly sneaks out and walks through the restaurant to another room where Chris is waiting for her. They think they are having a nice date but Holly keeps finding excuses to leave and Chris soon gets very frustrated. The girls don't seem to notice or care but Angela is miserable, and she finally tells Holly she did not want that party. Holly returns to Chris one last time, and when Chris learns the truth he leaves angrily. Outside, Holly hands him information about a photography job she found for him. She says it will let him fulfill his dream and give him more stability than a free-lance photographer would have. Chris is angry at Holly trying to run his life and do things for him when he doesn't want or need people to do things for him.Holly isn't through being made unhappy, as she has an unpleasant conversation with Angela, who says Holly tries to run other people's lives because she thinks she knows better than other people what is best for them. Angela says Holly is trying to plan the perfect wedding because it's the one Holly can't have, and it's not the ideal wedding for Angela. And Angela says she hates the dress. Holly ends up doing a lot of crying.The next day, the wedding is about to happen and Holly shows up at Angela's place with the expensive dress and says she gave up her trip to buy it. Angela is very happy. But when Holly visits Chris to give him the rings, he is cold to her and closes the door on her.So will the miracle happen between these two?