Songfacts®:

• Michelle Branch married her bass player, Teddy Landau, in Mexico on May 23, 2004 and gave birth to a girl named Owen the following year. The singer filed for divorce in February 2015, after ten years of marriage. On this song, she sings about how she sticks it out in a relationship even if it isn't working:
  
  I'm a hopeless romantic
  When I should run for my life
• Here, Michelle Branch reflects on the repercussions of falling in love.
  
  Everything is dangerous when it's just the two of us
  Jumping in over our heads
  
  "The song is about the push and pull of a romantic relationship," Branch told Entertainment Weekly. "There's always a kind of fear when you're entering a relationship with someone; of, 'Where will this go? Will I get hurt?'"
• Released in 2017, "Hopeless Romantic" is the title track to the first full-length solo album Michelle Branch released since 2003, when she was just 19. A lot happened in between: She formed a country duo called The Wreckers that had a #1 Country hit in 2006 with their first single, "Leave The Pieces," but broke up a year later. Branch then made two country music solo albums, but her label was in turmoil and all that came out of them was an EP released in 2010. She didn't head back to the studio - to make Hopeless Romantic - until 2015, after her divorce. Her producer was Patrick Carney of the Black Keys, who also co-wrote this song. They soon became a couple and married in 2019.
• The video was the first one Branch made since "Sooner Or Later" in 2009. Her friend, the photographer Brian Higbee, directed. "His stuff always skews a little bit darker," Branch said. "I wanted this to be darker. I haven't had a video out in so long, so I wanted to push the envelope in that sense, and not have something that was 'cheery' or what people expect from me."
  
  This one follows a tradition of Branch casting hot guys as her love interests. In the story, she picks him up in a old Volkswagen van but cuts him loose when he gets squishy about their relationship. In the end, he comes back around.