Whitney Port
Gossip

This week on The City, the gang headed to the Hamptons for some fun in the sun. Unfortunately, Freddie Fackelmayer was there, but that create some good drama.

Below, The Hollywood Gossip staff breaks down all the events of the latest episode of The Hills spinoff, awarding and deducting points as many points we see fit ...

Whitney Port and Roxy Olin stripping down to bikinis in the middle of Central Park, acting like there's no one around? Really? Eh, we'll buy it, and like it! Plus 4.

Safe to say Freddie Fackelmeyer didn't become less of a tool since last week's episode. Minus 2 for his hilariously fake tennis banter and attempt to look casual.

Erin Kaplan and Olivia Palermo are doing a feature on bloggers. Sure, they're fashion-oriented, not celebrity gossip-oriented, but nice industry shout-out! Plus 3.

Whitney, Roxy and Samantha Swetra roll to the Hamptons as "Good Girls Go Bad" plays. They talk about ... good girls going bad. Plus 3 for the Cobra Starship and Leighton Meester song, but Minus 3 for obviousness, so Even.

Olivia interviews some celebrity fashion bloggers and - here's a shocker - Erin doesn't think she does a good enough job. Seriously, the same plot every week? Minus 5.

Freddie Fackelmayer gets jealous when his 19-year-old brother Harry kind of flirts with Whitney. Lame, but we'll buy it, because Harry is much better looking. Plus 2.

Harry "lets it slip" (i.e. rats out) that Freddie has a girlfriend! Gasp, is it true? WTF! It's like The Bachelorette: Manhattan Blue-Blood Yuppie Family Edition. Minus 4.

Wow, Eric Zee finally lays the smackdown on Olivia! Plus 8.

Whitney: "Harry told me you have a girlfriend." Freddie: [pause] "But ... I don't know." Compelling response, you douche. Minus 3, but Plus 6 for Roxy chiming in, almost as an aside, that Harry was cock-blocking his older bro.

Another eye-rolling music tie-in: Beyonce's "Ego." Minus 1.

TOTAL: +8. SEASON TOTAL: -7. The City has picked up its game in recent weeks. We hate to admit it, but sometimes you need a complete putz like F-squared to stir up trouble. Sorta like The Bachelorette and Wes Hayden.

Seriously, MTV? This is the best you can do?

We realize The City is as scripted as The Hills, and you need to dig up a nice fake boyfriend for Whitney Port to date and pretend to make things interesting.

Laughably obvious as this strategy is, it at least makes sense to a certain degree. Deciding on Freddie Fackelmayer as the guy to fill the role? Not so much!

First, as N.Y. Magazine puts it, the commercial real estate broker has glaringly white bleached caps that "elevate his fake tan to Oompa Loompa proportions."

LOL, because that's not even that big of a stretch.

Clad in baby blue and pink, he is "a modern-day Nantucket-dwelling Poseidon who just body surfed from New England to Manhattan on a wave of hair gel."

It's hard to even take Freddie Fackelmayer seriously.

One could overlook these superficial flaws if Freddie Fackelmayer made up for them by being at all interesting. But he may be the most boring individual ever.

Moreover, he elevated his second-date awkwardness on this week's The City by bringing along his father, Fridolin (?!) to dinner with Whit without telling her.

Always a winning strategy, right girls?

Even though it's her own fault for agreeing to fake-date Freddie, we still felt bad for Whitney Port after the snobby dad patronized the living $h!t out of her.

No wonder they already broke up.

Maybe we're way off base, but somehow we doubt it. We need your opinion, ladies: Is Freddie Fackelmayer at all appealing, or as big a tool as we think?

Tell us: Would YOU hit it?

This week on The City, Whitney Port went on another date with Freddie Fackelmayer, while Jay Lyon also wanted to know the status of their relationship.

Below, THG staff members pick apart the latest episode of the Whitney-centric Hills spinoff, awarding and deducting points as we see fit throughout ...

In the opening moments, we learn that Whit basically booty-called Jay Lyon while he was back in town, then quit him for good. Hence the title. Plus 8.

Kelly says how she started her own company to promote things she believes in. Wow, now our interns are even less motivated to write this. Minus 2.

Olivia Palermo actually interacts with Roxy and Whitney this week! Amazing. It's almost as if she has a reason for being on the show. Almost. Plus 4.

Freddie Fackelmayer invites his father, Fridolin, out to dinner with Whitney. Minus 2 for Fred's faux pas, and Minus 1 more because Fridolin was so awk.

It takes Roxy Olin 12 seconds to realize Olivia is bad at her job and painful in general. She's perceptive, but Minus 1 because we still had to tolerate Olivia.

This is off-topic, but Roxy was on Brothers & Sisters this week and wasn't terrible. The fact that her parents are both on that show helps, but still, Plus 5.

Could MTV have set Whitney up with a lamer guy? Dude fake tans, bleaches his teeth, spends way too lonf on his hair and is not even interesting! Minus 10.

Samantha Swetra and Whitney debate if a dude can be a socialite. We don't know the answer, but if so, Whitney's fake boyfriend is so the epitome. Plus 2.

How long until Erin Kaplan goes postal on Olivia? Plus only 2, because they're dragging it out and she's too passive-aggressive, not aggressive-aggressive.

We never thought we'd say it, but we missed Jay Lyon. He's not without fault, but at least the guy has personality. Too bad this was just a cameo. Minus 3.

TOTAL: +2. SEASON TOTAL: -15. Scores were boosted by Olivia's integration into the rest of the show and the remergence of Jay and romantic tension.

It's got a long way to go, but positive steps, City. Positive steps.

Last night on The City, Whitney Port decided it was time she started dating again. MTV apparently agreed and dug up some guy named Freddie Fackelmayer.

Below, our staffers review the latest episode of The Hills spinoff and quote-unquote workplace drama, awarding and deducting as many points as we see fit ...

Whitney and Samantha Swetra compare designer shoes to boroughs of New York City. Even Gossip Girl wouldn't try to fabricate those stereotypes, but Plus 4.

At Elle, Joe Zee totally loves Olivia Palermo. Erin Kaplan totally doesn't! This not only feels contrived, we've been over it about 375 times by now. Minus 5.

Roxy Olin hangs out with a guy named Zac and expresses that she's jealous of Whitney and her life. Refreshing honesty, and use of a bra as a top. Plus 3.

Whitney decides she's going to date again. Enter Harry Fackelmayer, Sam's cute friend, who totally has a hot older brother! What are the odds? Minus 2.

Whitney agrees to meet up with Freddie Fackelmeyer at a barbecue. One that happens to be held at the apartment of Adam Senn and Whit's ex, Jay Lyon (who's out of town). How downright Kristin Cavallari of Whitney Port to show. Plus 7.

Kelly Cutrone tells Whitney to pee on the wall of the apartment to mark her territory. Plus 5, because that's funny stuff to hear from your boss, although we would have preferred if she instructed Whitney to top shelf the bathroom.

Adam Senn is a moron, but no longer really on the show, so just Minus 1.

Speaking of people who need to get kicked off the show, when will MTV pull the plug on Olivia Palermo? She has no redeeming qualities, her life is boring and has nothing to do with Whitney. Break out the pink slip already! Minus 24.

Putting aside the fact that his name is Freddie Fackelmayer, this Freddie Fackelmayer seems like a fairly large douche. La dee freakin' da, he works on Wall Street, wears preppy clothes and talks about surfing. Are we supposed to care? Minus 17.

Throw in another Minus 10 for the fake tan. In the Northeast.

But Plus 16 because we heard that they broke up before we even knew they dated, which is both hilarious and slightly comforting. Whit is redeemed. A little.

TOTAL: -24. SEASON TOTAL: -17. This week's scores are skewed by the sleep-inducing awfulness that is Olivia, but still, mediocre overall. Step up, City!

Whitney Port and Freddie Fackelmeyer. Yes, that's really him.

How lucky are we that the same celebrity style was recently rocked in frocks on the gorgeous frames of Whitney Port, Diane Kruger and Emma Watson?

Quite.

The actresses (we're not calling The City a reality show anymore, it's just not possible) added graphic appeal to their dresses with heavy black piping.

Obviously, when you bring together three young beauties like this, there can be no incorrect response. But whose look do you like best? Vote below!

Whose dress is best?

Last night on The City, Whitney again took Roxy's advice and tried to further her fashion aspirations, while Olivia butted heads with Erin yet again at Elle.

Below, our staffers review the latest episode of the new "workplace drama" (slash The Hills spinoff), awarding and deducting as many points as we see fit ...

Whitney Port has by far the best pronunciation of any celebrity. Girl paid attention in school. We even love how she says "Previously. On. The. City." Plus 2.

This isn't really relevant, but Spencer Pratt seemed pretty certain on Twitter that Whitney had plastic surgery in high school. Say it aint' so, Whit! Minus 1.

Roxy Olin on Whitney's designs: "I would definitely wear like half of those sketches. I'm very impressed." Plus 1 for that obviously backhanded compliment.

Surprise, surprise, Olivia Palermo looks bored and passive-aggressively feuds with Elle PR boss Erin Kaplan for the third consecutive week. Zzzz. Minus 3.

Kelly Cutrone rules. Plus 4. She doesn't beat around the bush at all when criticism is needed, but also tells Whitney Port she'll always be her "loyal bitch."

At the Roberta Freyman Showroom, and Rachel Roy's offices, Olivia attempts to show that she can hack it in this business. Can she? Still unclear to us, but apparently yes, according to her boss. Plus 2 for how much Erin hates it.

Minus 1 for Samantha Swetra trying to rip off that cute Lauren Conrad hairstyle!

Roxy is the Stephanie Pratt of The City. Useless, and just kinda there. Minus 3.

The Bergdorf Goodman buyer Whit meets with is named Sunni. Yes, Sunny, only spelled wrong. Minus 1. But Plus 2 for giving it to Whitney straight and kind of blowing her off. You can't expect to be a famous designer overnight!

Kelly on Whitney's visit to Sunni, which was Roxy's idea: "Yeah. It's always a good move to take advice from a girl from California who's been in New York all of two weeks and knows [bleep]." Burn! So sarcastic. So true. Plus 5.

Whitney Port as a celebrity fashion designer is something we can actually kind of buy. She seems invested in her career and at least semi-legit. We're only giving it a Plus 3, though, because that doesn't always make it fun to watch.

TOTAL: +10. SEASON TOTAL: +7. Not necessarily the most compelling half hour, but refreshingly light on the staged confrontations and BS this week.

Last night on The City, Whitney Port's pal Roxy Olin made quite a splash during one of her first days on the job, while Olivia Palermo struggled yet again at Elle.

Below, our staff reviews the latest episode of the new "workplace drama" (and The Hills spinoff), awarding and deducting points as we see deem appropriate ...

Roxy Olin: "I feel like I can get Kelly in, like, a second. I am, like, so serious about work." No. If you have to say that, girlfriend, it ain't true. Minus 7.

Kelly Cutrone drives a Ford so she doesn't get carjacked in NYC. Plus 4.

Meanwhile, over at Elle, Erin Kaplan assigns Olivia Palermo to buy some fake handbags off the street for an upcoming segment they're doing. The mere thought of this has gotta hurt for a silver-spoon fed rich girl like Olivia. Plus 3.

Their little sting not only involves a girl who's a quasi-famous socialite and on a reality TV show, but involves an MTV crew filming it. Real discreet. Minus 5.

In the end, Olivia can't even do this right. Work is, like, so hard compared to what she normally does. Which is, like, go to fancy parties and stuff. Minus 2.

Holy hell, that is one skinny model at the photo shoot. We're talking like Mischa Barton style. Minus 3. Way to promote a healthy body image, gang.

Roxy's big idea is for the model to get topless. A model for jeans. This is treated as if it were a revolutionary concept. Has no one seen a Calvin Klein ad before? All of their models are topless! Not that we're complaining. Even.

Plus 5 for Whitney warning Roxy that Kelly would be pissed if she didn't ask her before pitching this idea, and for being right. Always trust sage Whitney.

Poor Whitney Port worries that she's seen as the little girl that people walk all over. Don't be silly, Whit. You're the tall girl people walk all over. Minus 2.

The shady bag dealer is wearing a Konvict Muzik jacket. Akon would be proud. Plus 5.

TOTAL: -2. SEASON TOTAL: -3. Try it they might to make all this interesting, The City sort of falls short on execution. A lot more could have been done with Olivia's handbag drama, and there was far too little Whitney in general.

Last night on the season premiere of The City, Whitney Port was greeted by old friend Roxy Olin, who she tried to help find a job at People's Revolution. Meanwhile, at Elle, Olivia Palermo clashed big-time with new boss Erin Kaplan.

Below, our staff reviews the first episode of the new iteration of MTV's Whitney-centric Hills spinoff, awarding and deducting points as we deem appropriate ...

In the opening intro, Whitney reflects that nothing is the same as when she first moved to New York. In other words, MTV revamped the whole thing. Minus 2.

Roxy Olin makes her grand entrance two seconds in. Peeps are sure to mention her first and last names whenever they reference her. Solid marketing. Plus 3.

Whitney lives in the West Village now. Even, since both that area and Gramercy Park are quite trendy. Just pointing out that EVERYTHING is SO different now.

Olivia Palermo was apparently retained, and got a job at Elle magazine. Erin Kaplan is introduced as her boss. She's a tough cookie! Must. Create. Conflict. Minus 1.

Erin and her boss discuss how they're going to "break" Olivia and knock this "social" off her high horse. We're holding out hope for full-on hazing. Plus 6.

Whitney and Roxy meet for lunch and talk about how great it is to be single. Roxy reminds us a little of Stephanie Pratt. That's not a compliment. Minus 8.

Roxy may have been onto something when she bashed Whitney's fashion sense. Whit's outfit on the roof is heinous. Plus 1 in any case, though, because she's just so cute talking about how she doesn't want to annoy the neighbors.

"Do your job," Olivia instructs Erin, having been at Elle herself for like a day. Minus 3 for her pompousness, and Minus 2 more for The City casting another Erin right after Whitney's friend Erin Lucas got axed for being dull. Confusing!

Kelly tells Whitney Port that she hopes her friends are worth it and treat her as nicely as she treats them. Words to live by from sage Mrs. Cutrone. Plus 7.

Five guys and 30 girls at Roxy's party ... What's the opposite of a sausage-fest? Plus 3 for the girl who complained about this, but Minus 5 for the neighbor who called the cops on a pretty tame gathering. How lame is Whitney's building?

TOTAL: -1. Not the worst we've ever seen by far, but The City 2.0 still needs to step it up and decide what the heck it is before it becomes a must-see.

Lauren Conrad may have retired from reality TV, but that doesn't mean she's left her friends from The Hills behind. She and former co-star Whitney Port reunited onstage - and looked fabulous - as presenters on last week's VH1 Divas.

Asked to name the biggest diva she knew, LC didn't hesitate.

"Whitney Port?" Lauren joked, after which her taller, NYC transplant counterpart responded with a laugh, "I was just going to say Lauren Conrad."

Kidding aside, Lauren may not be keen on tuning into the new-look season of The Hills, but she is very excited for the premiere of Whitney's The City.

"She'll support me," Whitney Port said of Lauren.

The ladies talked about how they had a hard time adjusting to working with PR guru Kelly Cutrone, who complicates Whitney's life in the new season.

Two of THG's absolute favorite stars. [Photo: PacificCoastNewsOnline.com]

Whitney said she thinks her friend had even scarier encounters with Cutrone than she has. "I feel like you [had a harder time] because you had to meet her in that really awkward position at the runway show," Port said to Conrad.

"She's been kind of like a den mother to me," Whit added of her boss, who will be featured on The City. "She's been really, really great. I have no complaints."

"You know there are Devil Wears Prada situations, but it's a love-hate relationship. She has to be strict because that's the way she gets her business done."

Port also recently shared with us some of the "empowering" advice she got from another one of her mentors, celebrity fashion designer Diane von Furstenberg.

"Diane taught me a lot about empowering myself as a woman, and in my relationship world, she taught me a lot about appreciating and putting myself first."

New episodes of The City premiere Tuesday, September 29, at 10:30 p.m., right after The Hills. Follow the jump for a video of LC and Whitney's interview ...

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Earlier this week, we pitted Lauren Conrad against Whitney Port in a VMA fashion face-off after the glamorous twosome hit the annual MTV insane-o-fest.

Now the BFFs and former co-stars have come together again at the 2009 VH1 Divas special event at the Brooklyn Academy of Music in New York City.

Neither is known for disappointing fans with her style choices, so it comes as little surprise that both gals sparkled as usual. But who looked better?

Check out The Hills hotties and vote below ...

Who's the more glamorous VH1 diva?