High school is a time when many people form lasting friendships and relationships that can carry them through their entire lives. For some, these relationships turn into long-term romances and even marriage. As a result, high school sweethearts have long been a popular topic for songwriters, who have written countless songs about the joy and heartbreak of young love. In this list of the “Top 20 Songs About High School Sweethearts” we explore a range of genres and eras to highlight the best songs that capture the excitement and nostalgia of first love. From classic ballads to catchy pop anthems, these songs remind us of the sweetness and innocence of our youth, and the people who shared it with us. Whether you’re reliving old memories or making new ones, these songs are sure to strike a chord with anyone who has ever fallen in love during their high school years. So, grab your yearbook, put on your letter jacket, and get ready to take a trip down memory lane with these timeless tunes.
1. “Jack and Diane” by John Mellancamp
“Jack and Diane” is a classic song by John Mellencamp, released in 1982. The song tells the story of two young lovers, Jack and Diane, who are just trying to have fun and enjoy life. It is an upbeat and catchy tune, with a distinctive guitar riff and a memorable chorus that encourages listeners to “hold on to 16 as long as you can.” The lyrics paint a picture of small-town America and the innocence of youth, making it a timeless anthem that continues to resonate with audiences today. “Jack and Diane” remains one of Mellencamp’s most popular and beloved songs, and a classic of the American rock canon.
2. “Then” by Brad Paisley
“Then” is a romantic country ballad by Brad Paisley, released in 2009. The song describes a man’s deep and abiding love for his partner, expressing his desire to grow old with her and continue cherishing the memories they have made together. The lyrics are filled with poetic language and tender sentiments, accompanied by gentle acoustic guitar and Paisley’s smooth vocals. “Then” is a beautiful and heartfelt tribute to the power of enduring love and a reminder to cherish the special moments in life. It has become one of Paisley’s signature songs and a favorite among country music fans.
3. “You Never Can Tell” by Chuck Berry
“You Never Can Tell” is a rock and roll classic by Chuck Berry, released in 1964. The song is a celebration of young love and the joy of dancing, with a driving rhythm and Berry’s signature guitar licks. The lyrics tell the story of a teenage couple who fall in love and get married, culminating in a boisterous dance party with their friends and family. “You Never Can Tell” is an infectious and upbeat tune, with a catchy melody that has been featured in numerous movies and TV shows over the years. It remains one of Chuck Berry’s most enduring and beloved songs.
4. “Like You” by Bow Wow feat. Ciara
“Like You” is a hip-hop/R&B track by Bow Wow featuring Ciara, released in 2005. The song tells the story of a man who falls deeply in love with a woman and wants to be with her forever. The lyrics are romantic and heartfelt, with a catchy chorus and slick production that showcases the vocal chemistry between Bow Wow and Ciara. “Like You” is a standout track from Bow Wow’s career and helped cement Ciara’s rising star in the music world. It remains a popular choice for fans of early 2000s hip-hop and R&B.
5. “Perfect” by Ed Sheeran
“Perfect” is a romantic ballad by Ed Sheeran, released in 2017. The song is a tribute to Sheeran’s girlfriend at the time, and it describes the ups and downs of a relationship in a tender and heartfelt way. The lyrics are honest and vulnerable, with Sheeran singing about the imperfections that make his partner perfect for him. “Perfect” features Sheeran’s signature acoustic guitar and vocals, and it has become one of his most popular and enduring hits. It remains a favorite for couples and fans of sentimental love songs.
6. “Me and You” by Kenny Chesney
“Me and You” is a country love song by Kenny Chesney, released in 1996. The song tells the story of a couple who are in love and plan to be together forever. It features Chesney’s smooth vocals and simple acoustic guitar, which create a heartfelt and emotional tone that captures the feeling of being in love. “Me and You” was a breakthrough hit for Chesney and established him as a major force in country music. It remains a popular choice for weddings and romantic occasions, and it has become one of Chesney’s most beloved and enduring songs.
7. “High School Sweethearts” by Melanie Martinez
“High School Sweethearts” is a pop song by Melanie Martinez, released in 2019. The song tells the story of a couple who fall in love in high school and struggle to maintain their relationship as they grow older. It features Martinez’s distinctive vocals and a catchy, upbeat melody that belies the bittersweet lyrics. “High School Sweethearts” captures the nostalgia and longing that many people feel for the innocence and simplicity of their teenage years. It has become a fan favorite and a standout track on Martinez’s second album, “K-12.”
8. “Wherever You Will Go” by The Calling
“Wherever You Will Go” is a rock ballad by The Calling, released in 2001. The song tells the story of a man who promises to love and support his partner through all the ups and downs of life, even if they are separated. It features powerful vocals from lead singer Alex Band and a soaring guitar solo that adds to the song’s emotional impact. “Wherever You Will Go” became a massive hit and a defining song of the early 2000s. It has been covered by many artists and used in numerous films, TV shows, and commercials, cementing its place in popular culture.
9. “Love You Like a Love Song” by Selena Gomez
“Love You Like A Love Song” is a synthpop song by Selena Gomez, released in 2011. The song is an upbeat and catchy love anthem that explores the feeling of being infatuated with someone. It features electronic beats, synthesizers, and an infectious chorus that makes it a perfect dance-pop number. The lyrics revolve around the idea of love being like a song that you can’t get out of your head. The song was a commercial success and was praised for its catchy melody and strong vocals by Gomez. It became one of her signature songs and helped her establish herself as a pop star.
10. “Still the One” by Shania Twain
“Still The One” is a country-pop song by Shania Twain, released in 1998. The song is a romantic ballad that expresses the enduring love between two people. It features a mid-tempo beat, acoustic guitar, and Twain’s distinctive vocals that blend country and pop styles. The lyrics talk about the ups and downs of a relationship but also emphasize that the love between the couple is strong enough to withstand it all. The song was a commercial and critical success, topping the charts in multiple countries and winning numerous awards. It remains one of Twain’s most beloved songs and a classic of the country-pop genre.
11. “Apartment” by Young the Giant
“Apartment” is an indie-rock song by Young the Giant, released in 2010. The song features a driving beat, soaring vocals, and energetic guitar riffs that give it a lively, anthemic feel. The lyrics talk about the feeling of being stuck in a small, cramped apartment and dreaming of something bigger and better. The song’s upbeat melody contrasts with the melancholic lyrics, creating a bittersweet feeling of hope and longing. “Apartment” showcases the band’s unique sound and songwriting style and was a breakout hit that helped to establish Young the Giant as one of the most promising indie-rock bands of the 2010s.
12. “All My Life” by K-Ci & JoJo
“All My Life” is a soulful R&B ballad by K-Ci & JoJo, released in 1998. The song features smooth, emotive vocals over a simple, piano-driven melody, creating a romantic and intimate mood. The lyrics express the singer’s unwavering commitment to their partner, promising to love them forever and never let them go. “All My Life” became a massive hit and is widely considered a classic of the 1990s R&B genre. It showcases K-Ci & JoJo’s impeccable vocal harmonies and heartfelt songwriting, creating a timeless and universally relatable love song that has stood the test of time.
13. “Baby, Don’t Get Hooked on Me” by Mac Davis
“Baby, Don’t Get Hooked on Me” by Mac Davis is a catchy and upbeat song that warns a woman to not get too attached to the singer, as he’s not looking for anything serious. The track was a huge hit in 1972, peaking at number one on the Billboard Hot 100 chart. The song’s upbeat tempo and memorable melody, paired with Davis’ smooth vocals, made it an instant classic. The track has been covered by many other artists over the years, cementing its place in pop culture. Despite its age, “Baby, Don’t Get Hooked on Me” continues to be a popular song that is still enjoyed by many today.
14. “Crazy in Love” by Beyoncé feat. Jay Z
“Crazy in Love” is a song by Beyoncé featuring Jay-Z that was released in 2003. The song became a massive hit, reaching number one in multiple countries, and is widely considered one of the best songs of the 2000s. The song features a catchy horn sample, powerful vocals from Beyoncé, and a memorable rap verse from Jay-Z. The music video for the song, which features Beyoncé in various outfits and dancing energetically, became iconic and was praised for its stylish visuals. “Crazy in Love” is often cited as one of Beyoncé’s signature songs and a defining moment in her career.
15. “Catching Feelings” by Justin Bieber
“Catching Feelings” by Justin Bieber is a pop song with a catchy melody that tells the story of a man trying to figure out his feelings for a girl. The lyrics describe the emotional turmoil that comes with falling in love and trying to navigate a relationship. Bieber’s smooth vocals complement the song’s upbeat production, making it a fun and relatable track for listeners. The song’s bridge features an acoustic guitar solo, which adds a new dimension to the sound and provides a nice contrast to the rest of the track. Overall, “Catching Feelings” is a well-crafted pop song that captures the excitement and uncertainty of falling in love.
16. “Everytime” by Britney Spears
“Everytime” by Britney Spears is a haunting ballad about heartbreak and regret. The song showcases Spears’ emotional vulnerability, as she sings about the pain of losing someone she loves. The melancholy melody is accompanied by a simple piano arrangement, which adds to the song’s sense of intimacy. The lyrics touch on themes of love, loss, and the hope for a second chance. Spears’ delicate vocals are particularly effective in conveying the song’s message, making “Everytime” a poignant addition to her discography. The track was released in 2004 as part of her album “In the Zone,” and it remains a fan favorite to this day.
17. “Drivers License” by Olivia Rodrigo
“Drivers License” by Olivia Rodrigo is a song about heartbreak and the pain of seeing someone you love move on with someone else. Rodrigo’s powerful vocals and poignant lyrics capture the feelings of betrayal, loneliness, and confusion that come with a painful breakup. The song’s catchy melody and relatable lyrics have made it a viral hit, resonating with listeners of all ages who have experienced the pain of lost love. As a rising star in the music industry, Rodrigo has quickly become a voice for a generation, capturing the raw emotions of young people in her music.
18. “Love Like Crazy” by Lee Brice
“Love Like Crazy” is a country song by Lee Brice. It’s a song about a man who’s offering advice to his son as he begins to make his way in the world. He tells him to work hard, to be patient, and to never give up on love. The chorus encourages him to love like crazy, to take chances, and to hold on tight to the ones he loves. The song is upbeat and positive, with a catchy melody and relatable lyrics. It became Brice’s first top ten hit on the country charts, and it remains a favorite among country fans today.
19. “Fifteen” by Taylor Swift
“Watermelon Sugar” by Harry Styles is a funky, upbeat pop song with a playful and sensual tone. The song’s lyrics compare the sweetness of watermelon to the taste of a lover’s lips, creating a fun and flirty vibe. The catchy chorus is sure to get stuck in your head, while the funky guitar riffs and lively drums make it impossible to resist dancing along. Overall, “Watermelon Sugar” is a fun, summery tune that exudes positive energy and will instantly brighten up your day.
20. “It’s Your Love” by Tim McGraw & Faith Hill
“Bohemian Rhapsody” by Queen is a legendary rock classic that transcends genre and generation. The song features a complex arrangement of genres, including rock, opera, and ballad, showcasing the band’s musical range and creativity. The lyrics tell a story of a young man who has committed murder and is facing the consequences. The song’s operatic middle section features powerful harmonies and a memorable piano riff. Freddie Mercury’s soaring vocals and Brian May’s guitar solo have become iconic, making the song a beloved staple of rock music. “Bohemian Rhapsody” has stood the test of time and remains one of the most beloved and recognizable songs in music history.
Jared Parker is a frequent contributor to Singers Room. Since 2005, Singersroom has been the voice of R&B around the world. Connect with us via social media below.
