The truth is, we know nothing for sure about anybody named Valentine other than he was martyred like many other early Christians on February 14 and is buried outside of Rome. Maybe there wasn't even one Valentine. Valentine was actually a pretty common name and there were a lot of Christians martyred in Rome.
Around this time there was another one of those Roman Pagan celebrations of romance. We do love our pagan celebrations. It's way too complicated to get to the bottom of it.
But around the middle ages you get this wonderful story about a St. Valentine, that like most beautiful stories, is a true story, regardless of whether or not it really happened.
The Roman Emporium Claudius was smart enough to know that bachelors make better soldiers than family men so Roman soldiers were forbidden to marry. But Christian soldiers, ever the proponents of "Family Values" wanted to get married. Valentine was the priest to oblige them. His acts of civil disobedience ended him up in jail.
His jailor had a lovely blind daughter who came to visit him. He shared the gospel with her and she became a Christian. Some stories even claim he restored her sight. I prefer to think of her as blind, loving Valentine only through his stories of Christ. Theirs was a loving friendship, based on Christ. There's a romance for you. When he was taken away to be executed, he left her a note encouraging her to be strong in Christ. He signed it "Your Valentine"
If it didn't happen, it should have happened. And I'd be all for recovering a St. Valentine's Day about civil disobedience, not letting the State tell you who or whether or not you can marry, and friendship. And chocolate, because chocolate is good. As long as it's Fair Trade. Happy Valentines Day.