Remember when Ben Flajnik was devastatingly dumped midproposal on Ashley Hebert's season of The Bachelorette? Well, it apparently pulled at the heartstrings of Jennifer Love Hewitt. Flajnik and Hewitt only had one date, as he was purportedly in the midst of finalizing his deal as the next Bachelor.
He didn't go on to date Hewitt again, but following his season (where he chose Courtney Robertson and the relationship began fizzling even before the finale), there was a flash of romance between him and Kris Jenner. Yes, that Kris Jenner. They apparently hit it off after the two met wine-tasting, and there are paparazzi shots to prove it. Alas, as far as we know, he's super single right now.