It's so confusing. Luminescent scribe Jessica Joffe split up with scruffy musician Ryan Adams, who used to date Winona Ryder and Parker Posey and Alanis Morissette. (Ryan's been making inappropriate YouTube breakup videos for the past few days now, plus he sent us a poem). But did you know that George W. Bush, Open City editor Thomas Beller, big-time developer Roland Betts, and the secret society Skull and Bones also connect back to this sundered couple? Hunh? We need a diagram! (Click to enlarge.)

Don't you sometimes wish that somewhere out there, somebody is obsessively creating and editing videos about you? Seriously, it's creepily romantic. On that note, indie-ish musician Ryan Adams is at it again! This one features more of our favorite flame-haired scribe, Jessica Joffe—plus another poem calling her a "baby deer," plus sunflowers, plus a map of the West Village surrounded by a heart. In the "about this video" section, Ryan writes, "if shit is gonna be out there in no matter how small a dose, i thought i would rust off this tune. better days now mean reflecting on better days. Eh gnite." Ryan: soon you'll feel better and this will all seem like a bad dream, I promise. Click for the video!

Hey, kids! Still trying to make it in New York? Want to work in the fast-paced, exciting entertainment industry, for a "hip hop media mogul"? Are you "available and on call 24-7"? Got a recent pic of yourself ("for our files")? Then apply to be the personal assistant of P. Diddy! (Wait. Isn't it illegal to ask prospective employees to include a photo, unless they're an actor or model?) Anyway, Idolator hears that it's for a VH1 show. (As this job includes "coordinating business, social, and personal affairs," I'd just like to mention that I saw Mr. Diddy at an Eighth Avenue porn store several months ago. Don't ask.) Click for the memo!

Despite a rearguard effort by a few crusty old editors, the newspapers haven't been able to resist the popular fascination with female celebrities who have it all (ah, aspirational!) and then throw it away in a binge of alcohol, drugs and cheap publicity (ah, such delightful schadenfreude!). Paris Hilton, Lindsay Lohan and Britney Spears — playing the roles of fallen heiress, soused actress and white-trash pop star — have vied with eachother for media attention since they crossed over to the mainstream in 2003. As this chart shows, Paris Hilton was the first to break out into the supposedly serious media, in November 2003, when a private sex tape taken by her boyfriend hit the internet. Lindsay Lohan dominated 2005 with her eating disorder, but managed to get some attention for a movie, Just My Luck. This year's been the most competitive by far, with each of the three girls competing with DUI charges, jail terms, and breakdowns. And any squeamishness at newspapers and news weeklies has been overwhelmed by their need to remain competitive: they may disguise a gossip item in a worthy feature on teen alcoholism, but celebrity gossip is now all pervasive.

Our favorite millionaire underdog plans to sue the photographer who took the family photos of her that ended up on the over of OK! magazine. Dani Brubaker sold them to the tabloid for $1 mil, but they weren't supposed to be sold, or even public. Oops! (It's OK to date a paparazzo, however). Click the thumb to view the larger version of this grievous breach of trust. [Pagesix]

The new Ryan Adams YouTube video, which we can only assume is about his recent breakup with former Observer scribe, former model, and current ShopVogue writer Jessica Joffe, is called "Sad Days." Described as "found footage of dreams," it features a couple grainy shots of Jessica in all her redheaded beauty, plus shots of Ryan goofing around. Oh, the good times they must have had! Mostly, though, it features shots of the skyline racing by from the window of a car, or shots of the stars at night. Your next breakup could easily end up like this if you aren't careful! "He's obviously reaching out," writes a tipster. "Bless him." Click to watch! If you're looking for Jess, she appears about 2 minutes in, and again at 3:20, and at the very end.

Yesterday, we received a poem from someone calling themselves Romantic Danzig, titled "poem for Jessica Joffe because she blocked my email." Whatever! But then we received separate information that Joffe, the glam writer (Vogue! Glamour! Observer alum!) and former Banana Republic model had broken up with scruffy "difficult to work with" NYC musician Ryan Adams. She has been credited with helping Ryan overcome his substance abuse problems. (As you might remember, he's prone to piss-drunk Internet ramblings). The poem, totally/probably written by Ryan, follows—along with his touching explanation.

We totally get the desire to squeeze every last drop of drama from Britney Spears' meltdown. But US Weekly is running dry. Their latest online exclusive: Britney, who has a "penchant for X-rated clothing, as the celebrity weekly helpfully reminds us, took a sip of orange soda. "Oh, that's good," she said. (Click thumb for the screenshot.)

Writer Joanna Goddard is working on an article for New York magazine on—get this—New Yorkers who wear one color exclusively. But she needs your help! One assumes that all the men in black have already reported for duty, as this email pleads for those who wear only green. Click to view this vital memo!

Gwyneth Paltrow, that classy New York-bred actress, has fallen prey to what so many others have surrendered to: the damned raw food diet, or whatever people are calling their weirdo compulsive eating habits these days! (It used to be called "starving yourself.")

Jeff Bewkes ("pronounced byu-kiss"), Time Warner's new CEO, is nuts: ''A former colleague describes Bewkes, 55, as a quasi hypochondriac who fastidiously washes up after shaking hands ('If you've got a cold,' says the colleague, 'Jeff won't come anywhere near you') and can expound learnedly on the relative merits of various antibiotics.'' Who else is weird like this? Howard Hughes was an obsessive-compulsive, and Donald Trump famously won't shake hands either. Haven't they heard? It's the money that's dirty! [NY Mag]

It's the perfect business model. Finalpixx, the obscure paparazzo agency for which Britney Spears' boyfriend last worked, has scored a series of lucrative exclusives since he landed the troubled pop star. Now comes news that the Anglo-Afghan photographer, Adnan Ghalib, is also being paid by Spears to act as her personal assistant. Hollywood may be appalled by his mercenary nature; but the entertainment talent agencies at least must give a little grudging admiration for Ghalib's ability to make money at both ends.

What does David Patrick Columbia of New York Social Diary, a website that shares pics of the lives of the Tinsely Mortimer crowd, think of the growing income gap? He granted a rambling interview to BigThink, a "marketplace for idea-sharing, discussion between global thought leaders and the public" that's already interviewed luminaries such as Richard Branson and Ted Kennedy. His solution starts with the proclamation that, "A lot of people are just too rich." Like Donald Newhouse, one of Forbes' richest men, and the Rockefeller clan, presumably, all of whom have been lovingly chronicled on NYSD! He spirals into an anecdote about having dinner on the yacht of "a very, very rich man." The yacht in question was "big, huge... I think it was 300 feet or something like that. It was enormous." The video and transcript follow.

• Otherwise levelheaded Owen Wilson and scientologist Will Smith are being "driv[en] ... crazy" by Men's Vogue, which totally promised them the cover. [Daily News]

Julia Allison breaks up with Vimeo founder (and recent porn trafficker!) Jacob Lodwick after he refuses to take a meeting with Sequoia Capital. Julia is then spotted partying in Vegas with a Sequoia Capital suit named Mark Kvamme (pictured). And, finally, last night, Julia opens her heart to a conversation with Jacob to find — who could guess?? — that he says "things to me that I wouldn't say to the worst human being I know." [JuliaAllison.com]

She ran off yesterday afternoon with what must be the smoothest-talking paparazzo on the planet, Adnan Ghalib. Maybe she's coming here to check out the mental-health facilities at Bellevue? (They aren't nearly as nice as the ones in Cedars-Sinai, as Courtney Love remarked in a recent Myspace blog). Our recommendations for her trip to the Big Apple? We hear Bungalow 8 is a really fun club, and this place called Le Cirque is a pretty good place to eat. [TMZ]

"WHICH legendary american tv producer of late night comedy is been constantly seen walking back and forth at St Barth's Saline gay beach right around sundown?" Sic, sic, etc.

Last night while everyone losing their shit in Iowa watching the battle of the century, Britney Spears was waging her own legal fight. A flurry of paparazzi descended upon her home last night to cover her scuffle with the cops and subsequent hospitalization. But what's the nation's reaction? How did Obama and Huckabee stack up against Spears for media love? The results might surprise you.

Ashlee Simpson and Pete Wentz are not engaged, Us Weekly reports in a confessional apology for getting the story wrong (twice). They're getting good at confirming stories, especially when the stories are denials. But then they follow up with a reader poll: "Should Simpson and Wentz get married?" So at least they're focus-grouping the lies now. [RM]

BREAKING! We hear that Camille, that flower-behind-the-ear-having intern at Black Book who was spotted on the subway by Patrick Moberg and later located via the internet, isn't as into him as he is into her.