The accompanying music video for "Love Story" was directed by Trey Fanjoy, who previously directed the videos for the singles from Taylor Swift. Swift decided to collaborate with Fanjoy once again because she had been able to balance both of their ideas for music videos, something Swift appreciated deeply.[69] The video is a period piece that draws influence from the Medieval, Renaissance, and Regency eras. Swift had previously desired to film a period piece music video because of its distinctiveness from modern videos and videos she had filmed. When writing the song, she envisioned it in a prior time period, and encoded it with details accordingly.[70] She believed "Love Story"'s plot was a timeless scenario: "I think it could happen in the 1700s, the 1800s, or 2008."[69] Thus, she searched for a timeless quality in demeanor of her love interest.[71] With six months in advance, Swift searched by watching films for actors to interpret the role. An acquaintance of hers, who followed the sixth season of Nashville Star, recommended contestant Justin Gaston. Swift then looked through his pictures, and concluded he was suitable for the music video.[72] Gaston fulfilled the requirements Swift had set out, describing him as a "Prince Charming that could've been alive in the 1800s."[71] However, because Gaston was competing on Nashville Star, he was unable to participate in the music video. Gaston was eventually eliminated and Swift contacted him immediately to film the video.[69] Swift was very impressed by Gaston's acting skills: "I was so impressed by the way his [expressions] were in the video. Without even saying anything, he would just do a certain glance and it really came across well."[72]
A castle was chosen for the video's setting. Personnel researched numerous castles in the United States and were unable to locate one in sufficient condition for filming. They had considered traveling to Europe to find a castle, but were then informed about a castle south of Nashville, Tennessee. Named Castle Gwynn, a castle that is part of the Tennessee Renaissance Festival, both located in Arrington, Tennessee, it was built in 1973 and chosen as the video's setting.[69] Wardrobe for the video was supplied by Jacquard Fabrics, excluding Swift's dress for the balcony scene. The dress was designed by Sandi Spika with inspiration and suggestions from Swift.[69][70] "She loves to put her input in her dresses", stated Spika. The two had discussed the dress two months prior to the filming of the video. Accentuates were made on the video set.[69] The video was filmed in two days in August 2008 in Tennessee. On the first day, the balcony and field scenes were shot. On the set, someone had replaced the playback CD with a high-pitch, altered version of the song. As a result, Swift lent the crew her iPod to play the original track.[69] While filming another scene, sunset was about to occur and, therefore, the process was executed rather rapidly. For the scene, Fanjoy suggested a kiss between Swift and Gaston, but Swift refused to because she believed it would make for a sweeter moment. On the second day, scenes at Cumberland University in Lebanon, Tennessee and at a ballroom were filmed.[73] Swift learned the choreography for the latter in fifteen minutes prior to filming. Approximately 20 dancers were used for the scene.[69]
The video commences with Swift, clothed in a black sweater and jeans, walking through a university campus and spotting Gaston sitting under a tree, reading a textbook. As they make eye contact, the video then transitions to an earlier era, in what seems to be an 18th century castle, where Swift stands, wearing a corset and gown, and sings in a balcony. Afterwards, Gaston enters a party and sees Swift, wearing an elaborate gown, conversing with other young women. The two, along with others, engage in ballroom dancing. After dancing, Gaston whispers into Swift's ear and Swift is then seen pondering at night with a lantern. She meets with Gaston and the two walk, hold hands, and feed a horse by a well. The two then go their separate paths. Later on, Swift stands in the balcony again, looking out from the window. She sees Gaston running towards her and she immediately runs down the castle's staircase to meet him. Swift and Gaston meet in the field right in front of the castle and hold each other. The video then transitions back into the modern-day college campus as Gaston walks toward Swift and they gaze into each other's eyes, where the video concludes. Cut-scenes feature ballroom dancing and Swift performing in the balcony setting. To date, the video has over 440 million views on YouTube.
