Tonight You're Mine (2011)

"Two feuding rock stars get handcuffed together for 24 hours at a music festival where they are both due to perform."

- retrieve from IMDB https://www.imdb.com/title/tt1672845/

Liked this one with the music genre feel, plus always liked Natalia Tena from About a Boy and Game of Thrones.

Sing Street 2016

"A boy growing up in Dublin during the 1980s escapes his strained family life by starting a band to impress the mysterious girl he likes."

- retrieved from IMDB https://www.imdb.com/title/tt3544112/

Liking this one, gets a First Date Movie rating.  Songs are in the 80s genre, and are surprisingly good! Do check this one out!

Last Christmas (2019)

"Kate is a young woman subscribed to bad decisions. Working as an elf in a year round Christmas store is not good for the wannabe singer. However, she meets Tom there. Her life takes a new turn. For Kate, it seems too good to be true." [Retrieved from IMDB at https://www.imdb.com/title/tt8623904/]

Although ratings were low, from Jerry's view this one was a good one to the point of recommending it as a "First Date" movie. Yes, there is sadness and pain but no worries, your budding relationship will not suffer if it is on a solid foundation. Check this one out when you get a chance!