Songfacts®:

• Being a hopeless romantic isn't a bad thing - there's nothing wrong with falling deep in love. But in this song, Bogguss is a hopeless romantic in a hopeless romance. She desperately gives it one more shot, showing up at the guys house, hoping for a movie ending, but her hopes are dashed when she finds two cars in the driveway - he's not alone.
  
  Somewhat ironically, the song was the conduit for Bogguss' finest romance, the one that led to her lifelong marriage.
  
  In 1986, she had a regular gig performing at Dollywood and would earn a few bucks on the side singing demos in Nashville. One of the recording engineers she worked with was a guy named Doug Crider, who asked her to demo a song he'd written: "Hopeless Romantic." Bogguss loved the song, and sensing some affection from Crider, asked if she could record it - a bold request considering he was hoping a big name like Trisha Yearwood would take the song. To her surprise, he let her have it.
  
  "I think he had something else up his sleeve because he came to the session when I recorded it and he never left, so I think he figured, 'I'll give her this song and then maybe she'll give me her heart,'" Bogguss told Songfacts.
  
  Two months later, they got married.
  
  Bogguss included "Hopeless Romantic" on her 1989 debut album, Somewhere Between. It wasn't released as a single, but is a song dear to her heart because of the story behind it.
• The Somewhere Between album was produced by Wendy Waldman, who a few years later would co-write Vanessa Williams' #1 hit "Save The Best For Last." The album was named after the Merle Haggard song Bogguss covered as the first track. Haggard was one of her favorites growing up - Bogguss listened to his 8-tracks in the car when she learned to drive.