Enjoyed this movie - any similar movies you can recommend ?

Not exactly the same scenario but Lost in Translation springs to mind.
Some closer to home will spring to mind once I stop trying. I post then when they do.

"I wasn't totally sure what was happening. But I knew I wanted to stab someone."

Before we go
Nick and Norah's Infinite Playlist
Take Me Home
Away We Go
Conversations with Other Women
Before Sunrise
Before Sunset
Before Midnight
Stuck Between Stations
Tonight, You're Mine
Comet