Who- Fumikage Tokoyami x Tsuyu Asui
Canon Status- POSSIBILITY?
Personal Opinion- OTP
I think these two are really adorable for each other. Besides, I think Dark Shadow would be the one confessing on behalf of Tokoyami and Tsu just playing along and saying "Well tell Tokoyami that I love him, too" sorta situation.
They're perfect for one another basically.