"Kinks Shirt" by Matt Nathanson
What I really appreciate about this video is that the song makes no mention of the woman’s trans* status; they could have easily done something different with this video, and had Matt’s love interest be cis.
But no, she’s trans*, and most importantly, Character!Matt doesn’t care. They meet, they flirt, they sleep together, they talk over breakfast and clearly have a connection. That’s what matters, not the fact that this woman wasn’t born with a vagina.