When Whitney first met Jay, back before she officially moved to The City, drinks were flowing, sparks were flying and the flirting, giggling and hand-holding carried over well past midnight -- when Whit and Jay left the club. So what about Whit's new pseudo-beau/yachting partner, Freddie Fackelmayer? Well, despite Freddie's dashing good looks and bright, Nantucket tan, we're not really feeling the heat between Whitney and her socialite fellow. In fact, we're feeling something else - awkwardness.

From the "Surprise! You're on a date with my dad!" snafu to the seriously worrisome he's-friends-with-Olivia development, Freddy's already given Whitney plenty of opportunities to practice her "I'm Smiling On The Inside" face. And while he did apologize for ambushing Whitney with his dad, we're wondering why Freddie and his fair lady are having so much trouble getting their romance on in the first place.

Credit: MTV Remote Control