At last, Whitney Port's rumored new fictitious boyfriend arrived on The City last night. His name is Freddie Fackelmayer, and he beyond exceeded our expectations in the tan-and-shiny-skin department. Whitney could not have found a more polished, more orange fellow to date. Of course no one this tan, shiny, and skeevy can work out well. But her ex Jay is on tour having sex with other women, so she needs to get some action, too! Sadly, she somehow still hasn't figured out that Freddie the real-estate developer — who summers in the Hamptons and Nantucket, blow-dries his hair, probably has more boat shoes than she has orange dresses (which is to say a lot), and has probably slept with her friend Samantha — is exactly the kind of New York douche she needs to avoid.
Lesson 1: Shopping!
Do: Buy shoes if you’re independently wealthy and getting paid some astronomically unfair sum to babble nonsense on TV. Whitney and Samantha peruse the shoe section in Jeffrey, play with shoes, and don’t buy or try any on. We would have hated them if they bought a new pair of YSLs or something, but loved them for living out our unfulfilled spring shoe fantasies.
Don’t: Throw change into a fountain and wish for cute boys. MTV already hired them, ladies!
Lesson 2: Sourcing hot boys.
Do: Go where the lifeguards are. Whitney and Samantha go to a party at Bergdorf celebrating hot lifeguards (why weren’t we invited?). They could be dumb as bricks, but Whitney claims she doesn’t want a relationship, so who cares?
Don’t: Go to STK wearing a baggy sweater vest and bra. While Whitney and Samantha are trying to flirt with sexy lifeguards uptown, Roxy is at STK having drinks with some average dude whose name we can't be bothered to remember or look up. Of course she picks a guy with stubble. Of course she winds up in one of the most desperate sceney scenes on the West Side. Of course she wears only a baggy sweater vest with her bra entirely exposed. And of course she talks shit about Whitney.
Lesson 3: Being a good roommate.
Do: Have a life of your own. As in, go on dates when your roommate has something better to do (hot lifeguards) than hang out with you.
Don’t: Expect your roommate to take you around all the time. It’s interesting that Roxy expects Whitney to babysit her and take her wherever she goes because Roxy seems so intent on leading Whitney into her traps with her badass-ness, like a puppy into a pond with a strip of bacon. But she complains to her date that Samantha didn’t invite her to the party. “It’s weird — I feel like she excludes me on purpose,” she says. Well, with the pants she wears in public
Lesson 4: Wearing pants.
Do: Wear actual pants.
Don’t: Wear those leggings with slashes in the sides with just a T-shirt. Roxy does this at work one day. Whitney tells her she looks "sexy," like this is a good thing. Perhaps she lacks the vocabulary: A more fitting word might have been "ridiculous" or "inappropriate" or "desperate."
Lesson 4: Choosing a man to get some action with, part 1.
Do: Talk to the hottest boys in the room. It’s unclear if Whitney and Samantha truly chose the finest lifeguard specimens, but we’re guessing not because little Harry Fackelmayer from Greenwich was a Monet if there ever was one.
Don’t: Continue talking to the Monet if he’s a stereotypical New York douche. Here is what Whitney learns about Harry in her first few moments with him: He’s 21; he’s from Greenwich; he’s staying at the Yacht Club; he’s not that hot; he’s shiny; he’s overeager; Samantha knows his older brother from the Hamptons. Of all the things that turn her off, it’s his age, which is probably why he actually tells her he and his older brother Freddie would love to go with her to her ex’s BBQ so they can make him jealous. A classy gent would have thought that plan was weird, gone for another drink, and never returned, at which point Whitney could have smacked Samantha for having the bad idea to invite them.
Lesson 5: Networking.
Do: Be friendly with your co-worker, even if you don’t like her. Olivia’s story line involves no boys and is therefore almost entirely negligible this episode, but we can’t ignore her professional endeavors entirely. Joe forces Erin to let Olivia come to a fabulous Elle party at Carol Smith’s apartment so she can meet the Elle bigwigs and mingle with designers. Erin doesn’t trust Olivia to act like a decent professional human being, but Joe wants her there. At the party Olivia chats to everyone but Erin. This is her time — when the alcohol flows fast and free — to get on Erin’s good side.
Don’t: Tell your boss you knew everyone already. After the party Olivia tells Erin she already knew everyone there. What a good little socialite! Erin asks if she has any exclusive stories for them yet. Olivia doesn’t, which doesn’t make any sense if she really is friends with these people already. Erin scolds her for spending more time air kissing than trying to get scoops. When Erin offers to help Olivia with work, Olivia gets up and walks away. She probably had more important things to do than look at Style.com on her computer while Erin talks at her. Like put on more lip gloss!
Lesson 6: Going to a party where you will probably run into your ex, or into his friends at the least.
Don’t: Invite a crew of preppy-ass potential suitors who obviously won’t fit in. Let’s all take a moment to remember Jay and his BFF Adam. Shaving was not a daily requirement. Bathing might not have been either. They’re members of the “plaid mafia.” They don’t play tennis. This episode we see their living quarters are grungy. Of all the boys Whitney could bring to make them jealous, preppy, shiny people are not them. That set only gives Jay (and us) something to endlessly mock Whitney about.
Do: Make plans to meet potential suitors later. If Whitney were truly classy, she’d have looked as hot as possible without being skanky, gone to the party with only Samantha, and then said she had to meet her friend Freddie — “you don’t know him” — and dipped early.
Lesson 7: Choosing a man to get some action with, part 2.
Don’t: Go for the cookie-cutter New York douche. This is a classic mistake new girls to the city make. Whitney sees Freddie and becomes a melty mess at Jay’s BBQ. But WHY? Freddie Fackelmayer is a real-estate developer who starches his shirts and goes to the Hamptons and Nantucket regularly, where he probably engages in family tennis tournaments. He probably not only has a pair of Nantucket red pants, but wears them at least twice a month with a shirt from either Black Dog or Vineyard Vines. And boat shoes. He also probably pays Bliss prices to have his favorite facialist come over every morning to wax him (like a car) after his spray tan. Whitney must only find him sexy because in a way he’s exactly the opposite of Jay, who treated her like total crap. Also she wants to get in on the Hamptons action (another classic new-to-the-city-girl mistake).
Do: Try to find someone who isn’t made of plastic. Finding a nice guy in the city is not easy, but it’s not that hard to find a guy who doesn’t wax, tan, and put Vaseline on his teeth every day.
Lesson 8: First dates.
Don’t: Say you want to go to Nantucket with your new douche suitor. Freddie — looking totally overdressed in a big fat necktie — tells Whitney on their date he hangs out not only in the Hamptons but Nantucket. He tells Whitney she should go with him. Whitney says yes. Who makes plans to go away for a weekend on the first date? Samantha must really be rubbing her Hamptons action in Whitney's face.
Don’t: Ask if he had a fling with Roxy. Women should only ask potential boyfriends about past relationships to find out why they broke up with their last girlfriends. This way they can figure out if they broke up because of him and something douchey he did. No one should ask a date about a possible past hookup. Sure, Freddie and Samantha probably had sex. Whitney doesn’t need to ask, “Are you sure there’s nothing going on with Samantha?” Freddie doesn’t know what to say and only offers, “I’m here with you now.” That’s what boys say when they had sex with someone. We look forward to many episodes of Whitney torturing herself with this information.