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.

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 (and the City cameras) to go who-knows-where. 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-y fella. In fact, we're feeling something else instead: awkwardness. And a whole lot of it.

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

Shouldn't it be easy in the beginning? Or does insta-attraction have more to do with lust (and booty calls) than sweet emotion? Take the poll and tell us whether Whitney and Freddie need to stop with the nervous laughter -- and start turning up the heat!

We've learned a lot from brassy boss lady Kelly Cutrone over the years. And last night was no exception. Once again, the PR maven/unsolicited advice-giver stole the show when she advised Whitney Port to let her new man mark his territory -- all over Jay Lyon's toilet seat. And since we know we're not the only ones who enjoy Kelly's words of wisdom (or 'Cutronisms', as we like to call them), we thought we'd give you a rundown of our fave three KC-inspired life lessons. Starting with:

1. It is better to be feared than loved. Okay, fine, so Macchiavelli said it first. But nobody implements his respect-through-intimidation tactics better than Hurricane Kelly. The way Cutrone sees it, coddling is for the weak. So instead of sweet-talking her staff, KC motivates through scary pep talks and semi-regular firings. Remember: a fearful staff is a productive staff! (Well, usually.)

2. There's no shame in harassing the hired help. Seen any attractive underlings lately? Well, just cause you're signing their checks doesn't mean they're off-limits to your single/fabulous protegee! 'Member when Kelly set Whitney up with the adorable (though unfortunately super-tanned) Alex after ogling him at a model casting? Hey, it pays to be the boss.

3. Always be yourself. We all remember watching Kelly interrogate Allie the aspiring model about her weight. And even though Whitney asked politely, Kelly refused to back down. While not all of you approved of KC's bluntness, the People's Rev founder refused to do a takesies-backsies. Why? Because, after all, she's a bitch. And, like Kristin Cavallari, she totally owns it.

+ Got any Kelly Cutronicdotes we missed? Share 'em in the comments! Plus, listen to her sound off on Roxy Olin's very first day, and check the vid below to hear Kelly's own treasured memory: the time she screamed at someone because she "ended up flying in a middle seat in coach next to a really obese person." (We love you, Kel Kel!)

OK, so we don't know much yet about this Freddie Fackelmayer person, but who says you shouldn't judge a book by its cover? After all, if he's going to be courting our sweet lil' Whitney, it's important to get a sense of who we're dealing with and whether he's worthy of the City star's attention. Which is why we're using what (little) we know of Fred to see how he stacks up against Whit's ex, Jay Lyon. Below, we've created a score sheet for the guys -- check it out and see if you agree with our direct (yet reprehensibly superficial) analysis!

Category: Conversation Skills
Winner: Jay
Obvs, the Australian one wins! But on top of that sexy accent, Jay did have some interesting opinions about music and relationships and stuff. Two times out with Freddie and all we've really heard is that he thinks Whitney's "cute" (duh), he works in commercial real estate (well, hello there, Mr. Trump) and he's got three siblings (we'll take Harry, please).

Category: Posture
Winner: Freddie
To be fair to Jay, no guitar player stands up straight, but that doesn't take away from the simple fact that Freddie is taller (and darker and handsomer).

Category: Teeth
Winner: Freddie
Um, dude looks straight out of a Colgate commercial. And don't get us started on that shiny, fluffy head of hair, which probably smells of Kiehls shampoo and mint julep.

Category: Sense of Style
Winner: Tie score
This one's really a matter of opinion (er, unlike the others, which are total fact) ... though we're personally leaning towards Jay for the simple idea that his hipster attire can seamlessly transition from a day to night look with the subtle addition of a skinny tie, whereas prepster Freddie seems like he's all suit, all the time.

Category: Marriage Material
Winner: Jay
OK, sure, Jay's dream of being a rock star doesn't quite spell out emotional stability/financial security, but c'mon ... Whitney Fackelmayer?

Last fall, Whitney Port went for the rocker guy. This week, she's all about boys in blazers. And while her rumored relationship with Leonardo DiCaprio turned out to be nothin' but hype, we're thinking it's time Whit finally met her match. Since she doesn't have a "type," we've gone ahead and rounded up three eligible bachelors for our City gal to choose from. So cue the romantic music -- it's time to make like Patti Stanger and find Whitney a manz!

First up: James Franco.
Okay, so he's kinda easy on the eyes. But this Freaks and Geeks vet isn't your typical Hollywood heartthrob. For starters, dude says he's an artist first, actor second (the humble I-like-to-paint kind, not the pretentious, "acting is my craft" kind). Oh, and did we mention this soft-spoken Monet's also a secret genius?! When he's not off filming Spiderman sequels (or making us go through Kleenex by the box in Milk), Franco's sharpening his noodle with classes at NYU/Columbia. Smart, sexy and geographically desirable? Sounds like a triple threat! (Bonus: He played Justin Bobby in the best Hills parody ever. Marry him, Whitney! Marry him today!)

Next up: Ed Westwick.
This British bad boy has all the edginess of a wannabe grunge musician but without any of the unpleasantness (think greasy, "I forgot to shower hair") that goes along with life on the road. Best known for his portrayal of the smarmy-but-charismatic Chuck Bass on the CW's Gossip Girl, Westwick's trademark smirk/deadpan delivery make him the perfect foil for our sweet, adorable Whitney. And while he doesn't dress like his character off set (read: no custom Armani suits in used-car-salesmen plaid!), he's got a dapper, GQ style that would look great on any girl's arm. Or, better yet, in the front row at the next WhitneyEve show...

And, finally: Joseph Gordon-Levitt.
Levitt's soft, liquidy eyes melted our hearts in (500) Days of Summer -- but he's got a lot going for him besides his unconventional appeal. Smart, subversive and so small he can (almost) fit inside your pocket, he's survived thirteen years in the biz (remember Third Rock?) and gone from indie darling to lustworthy leading man without letting any of it go to his head. (Take note, Shia LaBeouf.) We've had a crush on him since 10 Things I Hate About You (dude was awkward/skinny hot way back when Michael Cera was just a fetus), and we think his grounded, hipstery appeal more than makes up for the massive height differential. Besides, no one at those Brooklyn loft parties wears heels, anyway.

+ Wanna help play love doctor? Let us know which single (or at least ring-less) guys you think would be great for Whitney Port!

Breakups are brutal. Fortunately, the majority of us get to experience the various stages of grief (i.e. anger, social withdrawal, the gratuitous use of sweatpants) in the privacy of our own home. Unless, of course, your name happens to be Whitney Port. Last fall, we watched as the City gal's on -- and off-screen -- relationship with rocker Jay Lyon crumbled right in front of our very eyes. So does Whit have any regrets about making her private life public? Hear what the still-single City star told our MTV News colleagues about falling in and out of love on the small screen.

After a less-than-smooth breakup with Jay Lyon last spring, Whitney Port's been way more focused on staying on Kelly Cutrone's good side than she has been on dating. Which may explain why the City star says she has more than a few dating disasters coming our way.

"It's difficult," Port recently admitted on Regis and Kelly Live. "My reality's obviously different than everyone else's -- my blind dates have like four cameras surrounding me!" 'Course, that doesn't mean it's okay for the guys to act like total duds. (Note to all prospective daters: If Whitney Port asks whether you're "having a fun time" the correct response is NOT "fun is a relative term.")

Annnnyway, hear what the up-and-coming designer told MTV News about her relationship status on The City (hint: she's not lookin' for another Jay!) and tune in tomorrow night at 10pm for an all-new episode.

The last time we saw Whitney Port on The City, she'd just turned her back on love (and ex-boyfriend, Jay Lyon) and promised to put herself -- and her career -- first. Since then, she's teamed up with her old boss, Kelly Cutrone, jumpstarted her design biz and welcomed an old friend (L.A. pal Roxy Olin) back into her life.

But things aren't always easy at the top. Whit may have left DVF and Olivia Palermo behind (Liv's stirring things up at Elle these days), but she'll still have to navigate around Kelly's temper/Roxy's backstabbing, and decide whether Samantha's "pal" Freddy is actually fair game.

Get a sneak peek of Whitney and Olivia's new lives, jobs and office frenemies, and tune in Tuesday, September 29th for the return of The City.

New episodes of Whitney's big City adventures are hitting the small-screen this fall. But that doesn't mean you'll have to wait til the last-minute to cram. Catch up on all the action (Olivia's DVF treachery, Erin's love life, Allie and Adam's fight nights and the Whitney/Jay saga) next week by pre-ordering the DVD now! The 13-episode, 3-disc set is available on Amazon next Tuesday (August 11). Happy early Labor Day!

+ Calling all Hills, City and ABDC fanatics! The Remote Control blog has officially gone global! Follow us on Twitter for your up-to-the-minute fix of MTV goss.

Lately, there've been lotsa conflicting rumors about Whitney Port's love life. Depending on what you believe, girl's either single and fabulous, coupling up with real estate broker Freddie Fackelmayer or falling back in love with scruffy music man/ex-boyfriend Jay Lyon. And while we don't know what to think (not even Page Six can keep their story straight!), we thought we'd take a moment to consider the possibilities.

Anyone remember those "Choose Your Own Adventure" books? Well, now's your chance decide what Whit should do next! Take our poll and let us know whether she should date someone new, get back with Jay or just enjoy being single next season. (No guarantee she'll actually listen, though!)