At this point in Jessica Simpson’s sad, sad career, it’s become clear that her only chance of making headlines is by sleeping with a new guy, getting dumped by that new guy, or whining over one of the many guys who’ve dumped and/or slept with her. As we learned this week, her most recent conquest — QB Tony Romo, who Jessica called “her future husband” in Glamour’s March issue before admitting that “this article could come out and Tony and I could be broken up” — rid himself of the Game Day Curse just as her ex-fling John Mayer was popping up all over the weeklies swapping spit with Jennifer Aniston and her fembot nips. Naturally, Jessica reacted by drinking herself silly and, we presume, making several late-night calls to her Dadager, Papa Joe, requesting her next romantic PR stunt stat. So the question is: which lucky bachelors will Joe pay off set her up with this time to guarantee continuous coverage of his darling daughter? Our suggestions, after the jump.

• This gold bust of Oprah features two dogs above her head, begins showing next week at a gallery and is intended to highlight "the overlooked threat of accidental pet fatality by common household products." [Oh No They Didn't] (Photo from Caplakesting.com via OhNoTheyDidn't)

An eagle-eyed Defamer operative caught a wonderful if short-lived revision at CAA's Wikipedia page this morning, when, for 30 precious minutes, the agency's storied history of talent relations included colluding with Joe and Ashlee Simpson to rip off her song "My Model":

• Tom Cruise and Katie Holmes are supposedly in the market for another screamless Scientology birth. [E!]

Sorry boys, It appears as if Scarlett Johansson really is taken. As we noted yesterday, 2006's Sexiest Woman Alive got engaged to equally easy-on-the-eyes boyfriend Ryan Reynolds, and judging from ScarJo's behavior last night at the Costume Institute Gala, the soon-to-be-bride appears incapable of hiding her joy. All smiles as she walked the carpet, Johansson even did the paparazzi a favor by flashing her new rock, and her choice to wear an off-white demure dress helped us paint some mental images of her upcoming walk down the aisle. But how does her ring compare to infamous engagement rings of the past (J. Lo's sad pink diamond monster mid-Bennifer trainwreck) and rings recently sported by newly engaged stars like Mariah Carey and Ashlee Simpson? We compare and contrast after the jump.

Has Joe Simpson gone from a pimpy fame-hungry Dadager to a bonafide nutcase? Not that we're surprised or anything, but his recent interferences with daughter Jessica's "relationship" with quarterback Tony Romo suggest there may be a few gurney-riding trips in his future. As OK! reports this week, Joe's intrusive behavior has Romo's family feeling like their son is being used and, even more disturbing, he showed up uninvited to a private Mexico vacation Jess and Tony took earlier this year. According to OK's source, "Whatever hopes Tony had of his relationship with Jessica turning into something real pretty much ended with Joe's stunt. According to his friends, they're pretty much just friends with benefits." But judging from Jess's romantic past, isn't Friend With Benefits pretty much her primary career these days?

We were admittedly underwhelmed upon hearing that lip sync princess Ashlee Simpson and her guyliner-sporting beau Pete Wentz were planning on tying the knot, but we are somewhat pleased to hear about all the trouble it's causing Papa Joe Simpson. Unsurprisingly, the engagement seems to be the result of Pete "doing the right thing" after knocking up his girlfriend. And in an attempt to turn a sticky situation into a pot of gold, minister-turned-Dadager Joe is allegedly trying desperately to make some quick cash by selling his daughter's story to the weeklies, conveniently timed to coincide with her upcoming album's release:

• Katie Holmes is said by Star to be planning a "trial separation" from Tom Cruise amid her plans to come to New York, where she might act in the play All My Sons. There's a battle over Suri. [Star]

• Us reported that Ashlee Simpson was pregnant, as did OK!. An October due date was even floated for the musician's baby. But husband Pete Wentz sent an email to MTV News denying everything and positing a massive conspiracy: "There is a witch hunt for people to be pregnant whenever they get engaged in Hollywood."

Just in case he hadn't officially lost all his "punk" cred already, Pete Wentz has successfully sealed the deal by getting engaged to lip sync queen Ashlee Simpson. And proving they're the ultimate modern couple, Ashlee made the announcement via (of all things) the website friendsorenemies.com in a post last night: "Yes, we are thrilled to share that we are happily engaged...We consider this to be a very private matter, and we wanted to be the first to tell you." Why exactly a "very private matter" is the sort of thing one willingly announces in the form of a blog post is beyond us, but one issue Pete feels more than comfortable discussing is his love of cross-dressing. As the bassist told Fox News recently,

• Ashlee Simpson confirmed she is planning to marry fellow musician Pete Wentz. [Sun]

Can somebody in America please buy one of my daughters' albums? Please? Or at least do a little more than pretend to like them or go a step beyond liking them for various reasons of irony? Do you know how hard it is to make the change between the manager who just got off the phone with the record label to the cool dad who has to the break news that one of them is about to get dropped from their label? It's hard, real hard. Let alone hiding these irrational fears that I'm going to get fired by my own daughters? Can you imagine that being fired by your own flesh and blood? It could happen. The constant threat that keeps me up at night. That and Ryan Seacrest changing his phone number without him giving me the new number.

Is Ali Lohan's new look just a matter of spiffing up her hair and makeup for the Living Lohan camera crew, or could she be the latest victim of Ashlee Simpson Syndrome? As you'll recall, Ashlee wasn't able to escape the shadow of her big sister until she went under the knife, and now it appears that lil' Lohan might be following her lead. Some recent shots of her out and about on the red carpet show a nearly unrecognizable version of her former clean-faced, mousy-haired, age-appropriate self. After the jump, we took a look at a few before and after shots to try and figure out if Ali's new hotness is the result of a knife or if she just found herself one hell of a hairdresser.

One unremarked aspect to that JuicyCampus article in the Times today is that it was written by Richard Morgan. Remember him? Morgan's the guy who quit Gawker after one day. Denton said he "spluttered out" after being unable to handle the site's fast pace, but Morgan claimed he quit because he wanted no part of all this nasty internet gossip. Morgan told New York mag that working at Gawker was "Hell" because "There is no vision beyond page views... Nick would tell me to post, like, something about Us Weekly getting Ashlee Simpson's engagement wrong. And then he wanted me to do another on Playgirl." With the much looser deadlines at the Times, it seems like Richard Morgan has no problem covering gossip blogs or discussing just who might be the sluttiest sorority girl at UC Irvine.

Monumental tool (and musician) Pete Wentz thinks he's really funny. And that he has something to say. So, like ya do, he made a video about it. It's a joke about celebrity culture and doing things for others and how sometimes celebrities are disingenuous about doing things for others. He has his monumental tool (and musician?) girlfriend Ashlee [sic] Simpson on hand to help him. It ends up being just a stupid Britney Spears joke that was made a few years ago, by funnier people. Oh and look! At the end, they call themselves assholes. Isn't that badass?? Pete should go back to opening shitty bars. At least then we won't have to hear him. Wait. Wait, no. No he shouldn't. He should go back to... He should just go. Video after the jump.

[Pop starlet Ashlee Simpson is surrounded by photographers in Los Angeles yesterday; image via Splash]

• LOL du jour: Britney's ratty VMA hair extensions were from Jessica Simpson and Ken Paves' product line. [TMZ]
  

Two equally frightening-exciting announcements this morning! How great! How scary!

In the real New York, bar bathrooms serve as fitting rooms for trying on potential pairings, an all-important step before making that one-night commitment. Luckily for us, Slut Machine has been around all the blocks. In this occasional column, she rates which restrooms of N.Y.C.'s watering holes are best for non-traditional restroom activities. It's liberating watching someone express her sexuality so wholeheartedly!

• Ashlee Simpson joins the nipple-slip club. (Kinda NSFW.) [Egotastic]