1. Taylor & Jake
Nothing impresses a girl quite like apples. And leave it to Jake Gyllenhaal to not only know this, but to incorporate it into a first date. Instead of taking Taylor to a swanky Manhattan bar, Jake really pulled out his cards by showing Taylor he could pick the biggest apple.
2. Tom & Katie
Tom Cruise didn’t want to take Katie Holmes on any an ordinary date. Katie was wined and dined in his private jet and fed the best sushi in the world.
3. Ben & Jen
Bennifer’s first date was a real classic. The pair spent the day at a Red Sox game cuddling up and splitting a hotdog. It was love at first bite.
4. Barack & Michelle
The president won over his future wife with a Baskin Robbins cone. They ate sitting on the curb.
5. Ashton & Demi
In happier times, Ashton and Demi shared a romantic first date at In—N-Out burger. In disguises, of course.