When: July 2011
Karlie Kloss was an 18-year-old model who'd done advertisements for Dior, Oscar de la Renta, Marc Jacobs and Chloe. She grew up in the Midwest and is three years younger than Joe. In other words, she fits the profile of a Jonas Brothers teenybopper fan. And as for their sighting together, the two watched Prince William play polo in Santa Barbara and took some goofy pictures in a photo booth.
Smash probability: Sometimes a polo match is just a polo match. With just a little effort, Joe probably could have made it happen, but we see no follow-through.