Songfacts®:

• "Trying On Rings" taps into Maddie Marlow's real-life love story with her husband Jonah Font. The pair first began dating as 15-year-olds, and five years later they impulsively visited a ring store and tried them on their fingers.
  
  Maddie Marlow had the song's title as soon as they left the shop and suggested the idea during a writing session with co-writers Tae Dye, Laura Veltz and Jimmy Robbins. The result is a nostalgic recreation of the story of their romance.
• Look at us
  Two Sugar Land kids looking all grown up
  Same ones that were too young
  To stay in love
  But here we are
  
  Marlow admitted to Taste of Country she'd been hesitant about turning her relationship with Jonah Font into a song, as it felt too personal. "I was really nervous to put my whole entire love story out there," she said. "But it was fun getting to explore the depth of our relationship and getting really specific."
• From, "Hey, can I get your number?"
  To, "Whatcha doin' Friday night?"
  Straight through a teenage summer
  To goin' on our fifth July
  From porch lights and swingin' on swings
  To real life doin' its thing
  From some silly 17 fling
  To tryin' on rings
  
  Maddie Marlow recalled to Apple Music how when she and Josh Font were in the shop trying on rings, they "both had the flashbacks back to when we were 15, 16 years old, dating in high school, me wearing his football number and things like that." The recollections surprised both of them, as they thought, "Wow, we've built something that has lasted this long and something that we're so proud of together."
• When Maddie Marlow and Jonah Font married on November 22, 2019 in a winter-themed wedding, the bride walked down the aisle to an instrumental version of this song.
• The song's heartwarming music video features home footage from both Maddie Marlow's marriage to Jonah Font, and Tae Dye's nuptials from when she got hitched to songwriter Josh Kerr in February 2020.
• Maddie & Tae aren't the first country duo to incorporate footage of their real-life weddings into a music video. Dan + Shay both got married in 2017 and they incorporated shots from their nuptials into the clip for "Speechless."