When Whitney Port agreed to meet Jay Lyon for dinner, she knew it was gonna be slightly awkward. Of course, it didn't help that he was less interested in catching up -- and more interested in lecturing Whitney about that random guy she brought to his apartment. Look, we get it, nobody likes hearing about their ex's new relationship. But bashing the man isn't the best way to save face - even if you were just trying to watch Whitney's back.

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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.

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AllieCrandellx "I don't know about the city yet, they haven't been filming and it could be possible that Adam and I won't be on the city!!" 40 minutes ago from web

Now, keep in mind this is not a verified Twitter account, so it may or may not be the real Allie. But if it really is her, then I think we have some worrying to do. Who will be left.. Whitney and.. ? Erin called it quits, Jay called it quits.

For now it seems Whitney and her two new "friends" Roxy and Samantha make up the cast of The City. Oh, and how could I forget supposed-love-interest, Freddie Fackelmayer?

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According to a Page 6 article, Freddy Fackelmayer, a commercial real estate agent, will be Whitney's love interest for the upcoming season. Could it be a match made in reality TV heaven? Whit was said to be cuddling with him at Lily Pond (picture below) over the weekend.

However, upon reading the Page 6 article, a source called to say, "The whole thing is fake. She had a little housewarming get-together on Thursday night and Freddie wasn't there." Friends of Fackelmayer insist the relationship is legit and confirm the recent canoodling in the Hamptons.

Later that night (Thursday), Port went to 1Oak for a Michael Jackson tribute, where she was spotted sucking face with - guess who - Jay Lyon.