Valentine's Day. Just another holiday in Jack's opinion, nothing more spectacular then Flag Day really. But still, that isn't to say Jack still had an ideal date.
If money wasn't an object Jack would love to be able to go to some fancy restaurant, get a four course meal, drink some nice wine that he'd probably secretly hate. Then after a walk through central part or some cheesey shit like that. The they would go back to is apartment or a penthouse hotel suite. Of course sex would be part of an ideal date, he was a 21 year old guy. It all sounded like the premise of some awful romantic comedy, but those movies make money for a reason.
To be realistic though, money wasn't easy for him. So he would have to settle for something like dinner at his favorite diner, maybe a movie , still a walk through central park, look at the stars. He would never tell anyone it, but deep down he was romantic. He wanted to fall in love, but didn't think it was really possible for someone to feel that way for him. The real him at least.