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If you watched this week's City, then you already know why we're head over heels for Whitney Port's pal Roxy Olin. Not only is this chick frickin' hilarious, but she's also got no prob sayin' exactly what's on her mind. Which is why she's now officially our new go-to gal for long car rides, raunchy tattoo confessionals and awkward public breakups.

And just when we thought we'd seen her whole bag o' tricks, Roxy blew us away by looking ab fab at Isaac Mizrahi's launch party Wednesday night. (The best part? She actually skipped out early to run home and watch the Yanks win the World Series! Our kinda girl!) Anyhow, check out these pics of the brassy brunette workin' it in head-to-toe black, and tell us whether you're lurving her as much as we are!

What's next for Whitney Port? Well, now that she's back to being single on The City, we figured she'd have lots more time to spend sketching, doing extra credit assignments and getting herself back on Kelly Cutrone's good side. But based on these scenes from next week's City, it'll be all Whitney can do to keep her job.

Next Tuesday, a misunderstanding between Whit and Roxy gets the girls into about-to-be-fired territory with the scary boss lady. Meanwhile, Olivia and Erin's constant bickering has Joe Zee ready to crack the whip! In this video, find out whose jobs (and friendships) are in serious jeopardy, plus get a sneak peek of what happens when you incite the wrath of Kelly Cutrone.

Finding out her new guy already HAD a girlfriend put Whitney in a pretty tough spot. 'Specially considering she was vacationing (at his house!) in the Hamptons at the time of discovery. So what should she have done? The way we see it, our City gal had two clear options:

1) Ignore it (for now), spend the rest of the weekend sunning herself by the pool/listening to bawdy stories about Roxy's crotch tat, then confront him back on her home turf. Or...

2) Accuse Fred Facks of being a total jerkface, storm off (to the sweltering heat of NYC) and leave him to rot in his luxurious Hamptons prison.

Now, in fairness to Whit, she didn't exactly PICK option No. 2 (it was more or less forced on her by She With The Tattooed You-Know-What), but we're wondering whether she should've let things simmah -- then given Freddie a chance to explain himself the next time they were alone.

+ Think peacing out of the Hamptons was the right move? Or would you have made the best of a bad sitch (think: beach party/girls' night out!) and saved the drama for later? Take the poll and tell us how you would've handled things if you were Whitney!

The tightly pulled-back hair. The sparkly (but not-at-all-dangly) stud earrings. The barely-there makeup (light foundation + a smidge of peachy-pink lip gloss/mascara). Yep, it's official: Whitney Port is turning into Olivia Palermo as we speak!

Okay, fine, so her personality's still completely intact (at least, from what we've seen so far on The City). But Monday night, at the Jimmy Choo for H&M event in West Hollywood, Whitney's look was a little (too!) reminiscent of her former DVF rival's.

+ Think we're seeing things? Or does Whitney's hair and makeup remind you of Olivia's trademark red carpet look? Check out some more pix of Whitney in action, then let us know whether you like her better with loose, tumbling locks -- or pinned-up Palermo hair!

Last week, daddy's boy Freddie Fackelmayer surprised Whitney Port with a romantic dinner for two three. This week, he brought her to a weirdo Hamptons rave (fun!) where his brother tried to kiss her and, oh yeah, told her Fred Facks ALREADY HAS A GIRLFRIEND. But is he as guilty as he looks? We thought long and hard and came up with five pseudo-convincing reasons for Freddie's sketchy behavior. Starting with ...

Explanation No. 1: Freddie DOES have a girlfriend. A loving, caring devoted (but tragically ill) girlfriend, whose dying wish was to know that he was already casually dating someone else. Sniff!

Explanation No. 2: Harry was totally lying. Possibly because he likes Whitney. Possibly because he's the worst brother in the world. Possibly both.

Read more...

OK, aside from taking on the perhaps unnecessary job of being Whitney's "mouthpiece," we're thinking Roxy Olin just upped her coolness quotient by a gazillion. After weeks of speculation about the newest City cast member, last night we finally got a true blue dose of what this L.A. implant is all about ... and we absolutely LURVVVVED it. Popping her head through the car's moon roof? Just what that snoozefest long ride needed. Piping up about sleeping arrangements at the Hamptons house? Someone had to ask! Crotch tattoo? You go, woman.

Plus, we now know for certain that Roxy's got Whitney's back. Maybe she overstepped her bounds a bit during pool time with those sketchy bros, but hey, it was obvs coming from a good place. And Fred "But...But...But" Fackelmayer really had it coming.

+ Are you diggin' Roxy's true colors just as much as we are? Sound off in the comments section about whether you're into the new girl's wild ways.

Either Whitney Port's got her own private wind machine or else she's just naturally blessed with the kind of long, flowy hair that only exists on runways/in music videos. So where was the City stunner going with those salon-perfect locks? Why, for a workout, of course!

Yep, Whit wasted flaunted those magical, tangle-free tresses on her way to the gym* this weekend, proving once again that -- after an hour with the flat iron and three outfit changes -- we STILL can't compete with famous people in black sweatpants. Which isn't to say we're ready to throw in the towel ... Now if you'll excuse us, we've got a blowout (and a personal training sesh) to schedule.

*Theoretically, she could also be coming back FROM the gym, but we refuse to believe hair can look that good post-cardio.

It's easy to be jealous of the new girl (especially when she's smart, stylish and extremely well-connected), but Erin Kaplan told the L.A. Times blog she's not threatened by her coworker/City costar Olivia Palermo -- she's just not that impressed by her, either.

"I think that when you start anywhere you kind of want to embrace the people around you," Erin said. "When I was new, I wanted to get to know everyone in every department. [But] I felt like [Olivia] was focused on accessories and that was it. That’s not really how it is at a magazine or anywhere."

So what are some of Olivia's strengths? Well, clearly there's her ability to work a cocktail party (note: it helps when you're already "friends" with everyone in the room), plus Erin admitted Liv has "great personal style" and said Joe Zee hired her because "he thought she was talented and had a good eye." Don't get any ideas about the two girls being friends, though. "Obviously, Olivia and I don't get along," Erin went on.

Fortunately, Erin seems to have clicked better with the rest of her City costars. "I really like Roxy [Olin]," she said. "I think she’s very funny. She’s very self-deprecating ... She’s fun to be around. Yeah, I’m a fan of Roxy’s. And as for Whitney Port? "She's very level-headed," Erin praised. "I adore [her]."

Whitney Port's got a few surprises coming her way on next week's City. The good news? She's heading out to the Hamptons for some fun in the sun with her hunky new boyfriend (and her roomie/pal, Roxy Olin)! The bad news? Whit's already hearing whispers that Freddie Fackelmayer's not as single as he seems. Watch as Whit's protective gal pal confronts Fred Facks about his so-called "shady" rep while Olivia Palermo and Erin Kaplan put on a two-woman revival of "Bring On Da Noise." Drama! Yelling! Leopard print bikinis! All that and more, on an all-new City.

When Whitney Port agreed to meet Jay Lyon for dinner, she knew it was gonna be slightly awk. 'Course, it didn't help that he was less interested in catching up -- and more interested in lecturing Whit about that random dude she brought to his apartment. Look, we get it, bro! Nobody likes hearing about their ex's new relationship. But dissing the tan man -- you know, Olivia's BFF? -- isn't exactly the best way to save face. Even if you were just trying to watch Whitney's back (and not, say, discourage her dating from Anyone Else But You).

+ Think Jay should've kept his opinions about Freddie to himself? Or is all fair in love, war and dinner with your ex? Take the poll and tell us whether Whitney's former flame crossed the line by weighing in on her new dude.