The boy who got away in fifth grade. His name was Jack - he had blonde spiky hair - it was the time of Billy Idol - a terrific tan and the most wonderful blue eyes. I recall me and my friends humiliating ourselves by serenading him with Rod Stewart's - Do you think I'm Sexy. His family moved away the summer before sixth grade - sigh.
There's this one girl who would be the happiest person in the world if she just loved me half as much as I love her. But we're not meant to be. And it's not through fault of me or her. And I would be a fool to pursue her.
If we're doing fictional, I'd probably date Daenerys Targaryen even if she turned into an ice zombie.
I quite fancy the Arrow's mother ... (at 43 i'm a bit to old to date Felicity) That aside Meg Ryan from the "when harry met sally" days , or Julia Roberts circa "Pretty Woman" Or Clare Danes from Homeland