Yesterday I mentioned that there are some couplings that are just so beyond the realm of psychological comprehension that our brains actually block them out. Then we were talking about Michael Jackson and Pamela Anderson. Today it’s a slightly less famous – though equally creepy – hookup.

According to the National Enquirer, Mary-Kate Olsen cheated on her boyfriend Nate Lowman by going on a date with “Superbad” actor Jonah Hill. They give an interesting account of the evening which I guess could be interpreted either way, depending on how you wanted to see it.

Mary-Kate Olsen is two-timing her boyfriend with a surprising new guy - chubby “Knocked Up” star Jonah Hill, the Enquirer has learned exclusively. The unlikely couple cozied up to one another at Los Angeles’ Chatuea Marmont hotel on Aug. 26 - just one night after the stick-thing actress stepped out to a rock concert with steady beau Nate Lowman.

“It was a shock to see Mary-Kate together with, of all people, geeky Jonah,” an eyewitness told The Enquirer. “They were on a double date with another couple, dining at the hotel around 10 p.m. Mary-Kate and Jonah sat close together and seemed totally into each other. They were both wearing plaid shirts that almost matched. It was the cutest thing.”

“From what I saw at the Chateau Marmont,” said another source, “Mary-Kate had forgotten about Nate and seemed totally enamored of Jonah. And he couldn’t keep his eyes off her, either.”

[From the National Enquirer, Sept. 15 2008, print ed.]

The magazine goes on to say how it appears that they were both genuinely into each other even though Mary-Kate went to a Radiohead concert with her boyfriend the night before. The Enquirer also repeatedly refers to Jonah’s size as “chubby,” “tubby,” etc, while referring to Mary-Kate’s diminutive size a lot too. While it does conjure quite the mental image – and leave a lot of questions about the physics of the thing, it sounds like the date could have been harmless or could have been a real date.

At one point in the evening Jonah saw friend Jason Segal and went over to talk to him. Supposedly Segal was genuinely surprised to see the two together and asked Hill how he got Olsen to agree to go on a date. Hill responded that all he did was ask her. Assuming the story is correct, it sounds like it could have been a date, but that doesn’t mean Mary-Kate was cheating on her boyfriend. They could have an open relationship, they could have quietly broken up, or it could have just been a friendly evening.

Here’s Mary-Kate Olsen leaving the Radiohead concert the night before her date with Jonah – wearing what I hope to God is her only plaid shirt. Header of Jonah Hill at Crown Lounge on August 27. Images thanks to WENN.

Comic Vince Vaughn, 38, seems to have found love again in the arms of an attractive brunette. He’s been seen out with the woman several times, and Mark Malkin of E! Online notes that Vince was having dinner with her and another couple at a sushi restaurant in Las Vegas on Monday night. The four blew through three bottles of wine and the restaurant stayed open an extra hour, until 1 am, to accommodate them.

This isn’t the first time Vaughn has been spotted out with his new girlfriend. Star Magazine identifies her as a 29 year-old real estate agent from Canada who was introduced to Vince by a mutual friend:

Vince has found new love with pretty Canadian real estate agent Kyla Weber, 29.

“It’s pretty serious,” says a source. “They’ve been dating for three months.”

Vince and Kyla - who lives in the small town of Okotoks, Alberta, and works for [a realty company - redacted] in nearby Calgary - met through a movie producer friend for Vince’s while Kyla was visiting pals in Vence Beach, California in May.

The two were spotted lunching at Little Dom’s in the Los Feliz district of L.A. on Aug. 3. Later that night, they were said to be kissing at a Dolly Parton concert. “Things are going great between them,” says the source. “Kyla’s racking up a lot of frequent flier miles going to L.A. to see him.”

[From Star Magazine, print edition, September 8, 2008]

I don’t know why it makes me happy to hear that Vince Vaughn has a new girlfriend he’s been with for a few months. Normally I don’t pay much attention to the guy and he kind of strikes me as a lout. Maybe it’s because his girlfriend is just an average person who happened to meet him through friends and romance blossomed. It’s also nice to hear when people are together but aren’t courting the spotlight. Plus another celebrity/non celebrity pairing might hold the promise of a wedding and babies, and it’s always nice to see a new person join the too-familiar celebrity circuit, ala Camila Alves and Luciana Damon. Best wishes to Vince and Kyla. I’m Not Obsessed has pictures of the two together.

Britney Spears seems to have really gotten her life together, and is looking amazing, to say the very least. But she’s gotten more than a few people worried that she’s in a two-steps-forward, one-step back situation. Apparently several of Brit’s family and friends are worried that she’s once again dating paparazzo Adnan Ghalib.

Just as things looked to be getting better for troubled Britney Spears it appears she has reunited with her badboy former lover Adnan Ghalib. The popstar is taking a break in Las Vegas before before [sic] attending the MTV Video Awards later this week. And she has been showing off her newly svelte figure, looking better than ever as she relaxed by the pool in a tiny bikini before heading out in a slim fitting sundress.

But also in the city is Birmingham paparazzi Adnan, who has been accused of having ulterior motives by Britney’s father Jamie… But despite Britney’s father’s staunch disapproval of Adnan, the pop star is understood to have started seeing Adnan again, TMZ.com reported.

However sources claim the two haven’t got back together for purely romantic reasons - Britney is apparently terrified Adnan has an explicit video of her, filmed during the couple’s brief trip to Mexico in January. ‘Britney’s really scared that Adnan has a sex tape,’ an insider told MailOnline last month. ‘She wants to get it out of his hands.’

Britney’s father, who is still her legal custodian following a legal order earlier this year is said to have made his dislike of Adnan obvious. ‘Britney’s father can’t stand Adnan,’ said the source. ‘He thinks he’s seedy, with ulterior motives.’

[From the Daily Mail]

Rarely do you find yourself thinking about two people, “Wow, I hope he just has an explicit sex tape and they’re not actually dating,” but in this instance I really hope that’s the case. If Adnan was threatening Britney with a tape, she’d at least have a healthier motivation for being around him. If she were dating the guy again, I can’t even imagine what kind of psychological trouble she could get herself back into.

And she really has worked hard. Everyone kept saying how great she looked – and it was clear she was much healthier. But with these pictures from this past weekend, it looks like Brit’s arguably in the best shape of her life.

Here’s Britney with her friends and security at the Mirage Hotel and Casino on her way to The Beatles Cirque De Soleil performance in Vegas on Sunday. Images thanks to WENN.

Well John Mayer is back to his manwhoring ways. Not that anyone’s surprised – the only shocking part of the revelation was that it took him so long. Okay in all honesty Mayer probably waited all of half an hour to boink a new chick after he and Jennifer Aniston broke up. And it was only that long because he had to stop to fill up his gas tank and grab some Doritos. Nothing helps you out with the ladies like a guitar and some nacho cheese breath.

But In Touch is officially (as in “stop the presses!” officially) reporting that Mayer drunkenly hooked up with a cocktail waitress last night – and he also claimed he didn’t want to have the number one song on the charts.

While he may have started a whirlwind romance in Miami with Jennifer Aniston a few months ago, John Mayer ended his two-month world tour by partying with a different blonde in, yep, Miami. (This time around, the blonde was a cocktail waitress, not an A-list actress.) The singer was as talkative as ever on-stage, admitting, “We’re all drunk. Only on-stage can you openly drink on your last night.”

He then went on about the downsides of fame: “I don’t want to have the number-one song. I want to be number eight. It’s a much better place to be. Because as soon as you become fashion… you get crushed.” And though he didn’t mention his ex Jennifer he did say at one point, “I had a conversation recently and a lot of tears were exchanged.” Post-show, John went to the club SET on South Beach with his waitress, where they stayed until about 3 a.m.

[From In Touch]

So it’s pretty clear where In Touch’s loyalty lies. And if you’re unclear, click the link to the article, and then take note of the article’s address. What an unfortunate (and I’m sure accidental) place to cut off the title: “John Mayer ends tour with cock.” I’m sure it’s just some requirement of their technical programming.

I love John’s great quotes from the night. “Only on-stage can you openly drink on your last night.” I think he meant “Only on your last night can you openly drink on-stage.” But I could see how all the drunkenness might make the technicalities of that complex sentence a little tough to get out. And then the thing about wanting to be number eight instead of number one.

That’s like when I claim I don’t want to be thin, and it’s really much healthier to be chubby. No one believes it, you’re just trying to convince yourself. We’d all like to weigh 20 pounds less and have a number one Billboard single. It’s a universal truth. But when you can’t have that, might as well settle for nailing a cocktail waitress.

Here’s John performing in concert at the Cruzan Amphitheatre in West Palm Beach on Sunday night. Photographer: Michael Allen. Images thanks to WENN.

Country singer Carrie Underwood, 25, and world record-setting Olympic swimmer Michael Phelps, 23, have been talking on the phone and texting back and forth. They haven’t met yet but they’re planning a date to take place in Nashville soon. Phelps is said to have heard that Underwood called him “cute” and that paved the way for the two to get in touch.

[Michael Phelps] is totally smitten with Carrie after her heard that she thought he was “cute,” say sources at the 2008 Olympics. They began texting and calling one another while Michael was still in Beijing and have already made plans to get together in Nashville, near where Carrie lives. Carrie suggested “a quiet dinner” as a first date, said the source.

“But Michael laughed and said, ‘I’m not so sure that you’d want to see me eat! It might not make a good first impression.’”

[From The National Enquirer, print edition, September 9, 2008]

That’s cute that he said he doesn’t want her to see him eat. The Enquirer reminds us that Phelps has to consume 12,000 calories a day while he’s in training to keep up his energy. That’s more than a lot of people eat in a whole week.

I don’t really see how this guy is so attractive. He is an amazing and heroic athlete who demonstrates triumph of will and deserves to be lauded. He’s not a traditionally good looking guy when he puts a shirt on, though. I don’t see him lasting with Carrie or it going beyond a first date or two. She comes off as petty to me, and she’s clearly not over her failed relationship with Tony Romo given some of the things she’s said about him. Phelps just doesn’t seem like her type. That said, JayBird is single and open to giving the guy a chance despite his physical oddities.

Carrie Underwood is shown at the CMA Music Festival on 6/7/08. Credit: Judy Eddy / WENN. Michael Phelps is shown at an event to announce the “Visa grant for early swimming” on 8/28/08. Credit: L Gallo / WENN

Earlier in the week there was a lot of speculation about record-setting Olympian swimmer Michael Phelps’ love life. The buff athlete graces the cover of Sports Illustrated and stands to earn millions in endorsement deals. He’s one of the hottest commodities around, but fellow American Olympic swimmer and Playboy model Amanda Beard denied hooking up with him, saying “Ewww, that’s nasty” when she was asked about it. British model Lily Donaldson hasn’t commented on a rumored romance with Phelps, but there’s at least one lovely Olympian who didn’t pass up a chance with the 6′4″ powerhouse.

Phelps, 23, was spotted making out with Australian three-time Olympic gold-winning swimmer Stephanie Rice, 20, at a party on Monday:

Phelps, fresh from shattering Mark Spitz’s 36-year-old record, was spotted Monday night in a hot make-out session with Down Under swimmer Stephanie Rice, a source tells The Post’s Clemente Lisi and Luke Dennehy. The pumped-up pair clinched and swapped spit at a celebratory bash outside the Olympic Village.

The Baltimore Bullet swooped in for the lip-lock with the 20-year-old brunette just weeks after she split from Aussie swimmer Eamon Sullivan. “All the swimmers are talking about it, and [Sullivan] is cut up about what happened,” the source said.

The day after the face-sucking frolics, Phelps and Rice cheekily posed together for Speedo - laughing and playfully groping each other as a photographer snapped them in their swimsuits. “I definitely admire him for his athletic ability and everything he’s achieved,” gushed Rice, who won three gold medals of her own. “I’m just really glad to be in the mix with that.”

Whether the dynamic duo is now a couple isn’t known. Phelps’ rep didn’t return our calls.

[From The NY Post]

I know these two are young and this may not last for them, but could you imagine what great athletes their kids would be? Rice has a couple of world records under her belt too.

Once the Olympics come to an end on Sunday Phelps will have a great new place to relax and entertain the women that are sure to flock to him. He’s purchased a $1.69 million dollar condo on the river in his hometown of Baltimore, Maryland. He can surely afford a much bigger mansion, though. US Weekly reports that his lifetime earnings are estimated to come in around $100 million and that he already has endorsement deals with PowerBar, Omega, AT&T Wireless, Visa, Speedo, and Kelloggs.

Here’s Stephanie Rice winning the gold medal in the 200M individual Medley on 8/13/08. Credit: Insidefoto / PR Photos

When I first heard the story that Michelle Williams, 27, was dating director Spike Jonze, 38, I was pretty skeptical. The rumor seemed to originate in Star Magazine and was based on the two sharing a goodbye kiss that lasted too long outside Jonze’s apartment. Michelle and Spike worked together on the film Synecdoche, New York, and there wasn’t much evidence that they were a couple. The late Heath Ledger’s best friend from Australia, Trevor DiCarlo, was staying at Michelle’s place for a while and I guessed that he was her new love interest, not Jonze.

Jonze and Williams were spotted together at the airport last week boarding a private plane to Oregon with her daughter, Matilda, 33 months. They were also seen kissing at dinner in LA on August 2. It looks pretty obvious at this point that they’re a couple.

Michelle Williams and director Spike Jonze, who were recently spotted getting cozy together in Brooklyn, have taken their relationship bicoastal.

The twosome shared an intimate dinner at Little Dom’s in Los Angeles’ Los Feliz neighborhood on Aug. 2. According to a fellow diner, Williams, 27, and Jonze, 38, started off their late-night meal sitting across from each other. “During dinner they would lean in and kiss each other over the table,” the diner says.

By the end of the meal, Williams had hopped into Jonze’s lap and the pair were smooching, according to onlooker.

Jonze, the ex-husband of Sofia Coppola, produced the actress’ upcoming film Synecdoche, New York. At the Brooklyn deli, the director “had his arm around [Williams] and kissed her on the cheeks, then on the lips,” PEOPLE reported recently.

[From People]

Jonze was married to director Sofia Coppola from 1999 - 2003 and was briefly linked to actress Drew Barrymore last year.

Michelle doesn’t seem like the PDA type to me at all and I’m really surprised that she would sit on a guy’s lap at a restaurant and start kissing him like that. She must really be crazy for him, and it sounds like the feeling is mutual. Jonze must be the affectionate type and these two sound like they’re head over heels for each other.

Michelle Williams and Spike Jonze are shown at a photocall for Synecdoche, New York in Cannes on 5/23/08. Credit: Axelle/Bauergriffinonline.com

68 year-old Monty Python star John Cleese is in a new relationship with the VP of marketing at Radar Magazine, 34 year-old Jane Smiley. The two went on a vacation with to Italy and Switzerland recently and the Daily Mail has quotes from both of them on their new relationship. There’s also a photograph of the two of them together, with Smiley looking a little sheepish. It’s hard to believe they would speak so candidly to the Daily Mail, and it’s possible these quotes are taken from somewhere else or even fabricated given the source. The Mail phrases things so vaguely that it’s hard to tell when they’re telling the truth or have an exclusive interview. Even a friend of Cleese who joined the couple briefly on vacation chimes in to say that he didn’t think they were hitting the sheets - before they went on that jaunt to Europe together. Cleese is going through a divorce from his third wife of over 15 years, Alyce Faye Eichelberger, and his friend jokingly calls the vacation with Smiley a “divorcey-moon.”

Cleese spied his opportunity when his old friend Michael Winner, the movie director and restaurant critic, arranged a six-day road trip to Switzerland and Italy.

The 72-year-old Death Wish director dubbed it the ‘Divorcey-moon’ to mark his friend’s split from therapist Alyce Faye Eichelberger after 16 years.

When the two men reached Zurich, Miss Smiley flew out from the US to join them, and she and Cleese continued their journey alone through Switzerland and Italy to Vaduz, Lake Como and Bergamo.

Cleese explained: ‘We met in New York at a power breakfast and spent a few days together in Switzerland and Italy and we liked each other a lot, but the problem is she works in Chicago for a magazine and I’m in California and London.
‘I am not sure when we’ll be seeing each other again. Unfortunately we are living very far apart citywise.’

Miss Smiley said: ‘We met a few weeks ago at the Regency Hotel in New York and we had this natural connection and became firm friends.

‘We’re at the stage where we are still getting to know each other.

‘At the moment it is a very close, very warm friendship.

‘He is twice my age. He’s very stimulating and extremely funny and charming.

‘I’m American and had never heard of Monty Python or Fawlty Towers, although I had seen A Fish Called Wanda.’

Winner, who dined with the couple in Zurich, said: ‘It was almost a blind date.

‘I don’t think they’d had a major consummation before that, if I may put it that way.

‘She’s delightful and definitely a girlfriend.’

Cleese has been in London working on a series of projects including recording a commentary for a new set of BBC DVDs for Fawlty Towers.

[From The Daily Mail]

If Smiley grew up in America she’s not likely to use phrases like “firm friends,” and it sounds awkward the way they have her speaking so stiffly and saying obvious things like “He is twice my age.” Maybe everyone talked to the Daily Mail assuming they’d make up and embellish shit anyway, but I doubt it. Good for these two, though. They’re both single and old enough to make a decision about who they want to date. It doesn’t seem like it’s going to work out given the way they’re presumably talking about it. It sounds like they’re interested in each other because they found a connection but that they’re not sure they’re right for each other given the age difference. That kind of spark doesn’t always evolve into a romantic relationship, but they’re giving it a chance anyway.

I’m constantly amazed by the seemingly random hookups between celebrities, single or otherwise attached to other people. The young celebrities seem particularly prone to in-dating, which makes sense because they’re the ones who are less likely to settle down.

Kirsten Dunst, 26, was spotted out looking bleary eyed and walking hand in hand early in the morning with Justin Long, 30, whose separation with girlfriend Drew Barrymore was just announced. It’s assumed that since Kirsten and Justin - that has a cute ring to it - were together in the morning that they spent the night together. And they were holding hands and kissing so it’s not likely that one of them just crashed on the couch because they were two drunk to drive home.

“Justin was holding Kirsten’s hand while walking around downtown NYC in the SoHo area,” an eyewitness tells OK!. “They looked like they had stayed out all night and Justin had bloodshot eyes, but Kirsten was all over him and kept leaning in to kiss him.”

Perhaps they were heading to the 30-year-old’s new digs — Justin recently purchased a $2.4 million bachelor pad in the Big Apple.

The scene was in stark contrast to Justin’s disposition less than a week ago when he was still reeling from his split with Drew. While out at Westside Tavern on July 12, the actor looked “heartbroken,” a source tells OK!.

[From OK!]

Dunst was most recently casually dating a 25 year-old DJ/actor named Matt Creed. In Touch reported last week that they were seen eating out one day and out at a bar together a few days later.

Kirsten tends to hold her relationships close to her chest so it’s not likely that we’ll be hearing gushing reports about how great Long is or seeing the two of them hit the paparazzi targets like he did with Barrymore. It seemed like Barrymore was the one who wanted to announce her relationship with Long to the world and that he just happily went along with it. He seems like a great guy and he doesn’t strike me as the grungy rocker type that Dunst seems to usually date. Maybe he’s just the kind of guy that she needs now. I think I see the faintest hint of a smile on her face in these pictures.

Kirsten Dunst is shown out in Soho on 7/9/08. Credit: Anthony Dixon / WENN. Justin Long is shown out at Villa on 5/24/08. Credit: WENN

Cher in March, 2006. Credit: PRPHotos. The pictures of her with her new boyfriend are in this week’s Enquirer
The National Enquirer has a new cover story this week which reads “Cher’s Secret Wedding!” It’s technically accurate according to the information they claim to have, but is misleading because Cher is just said to be planning a wedding with this biker dude who happens to be 24 years younger than her, and hasn’t actually married him yet. So a more accurate title would be “Cher Plans Secret Wedding!” But that’s ok, because the details are juicy enough to make up for the inaccurate title.

Cher met 38 year-old Tim Medvetz through her friend Richard Stark, the designer of Chrome Hearts Jewelery. Medvetz is a 6′5″ tough biker dude with long black hair and one of those half goatee mustache combos. He customizes high end motorcycles and was injured so badly in a motorcycle accident in 2001 that he had to have his back fused together and metal plates put in his skull. The guy was in a wheelchair for 6 months, but he decided to set a goal for himself to climb Mount Everest, and he made it on his second try in 2007. He’s said to drink a lot of whiskey and love fried chicken, but he lifts weight to work it off. Cher’s boyfriend’s story is pretty interesting, and he’s a determined guy but that doesn’t make him marriage material.

Medvetz and Cher have been spotted out together and have traveled together. The Enquirer’s information that they’re planning to get married seems sketchy, though, and could be based on a quote Cher gave that “I could see myself getting married again.” Cher has been married twice and has two children.

The May-December couple spent a night nuzzling at the Foxtail lounge in L.A. on June 13, accompanied by Cher’s close pal, actor Dean Winters, along with Richard Stark and wife Laurie, according to the source.

“Tim was so protective of Cher that everyone assumed he was her bodyguard.”

Their love burst spectacularly in the open when they recently traveled with the Starks to Nashville to see country music legend Merle Haggard.

Cher rented a private jet for the flight and took Tim and her posse to The Bluebird Cafe on June 24.

Next, it was on to Tootsie’s Orchid Lounge, a famous watering hole.

The couple spent the night together in a beautiful suite at The Hermitage Hotel in Nashville, according to a local insider.

[From The National Enquirer, print edition, July 21, 2008]

As for Cher and Medvetz’s plans to marry, the Enquirer says they plan to marry “in a quickie Las Vegas ceremony by the end of the year,” and that Cher is asking him to sign a prenup first to protect her assets. There’s not much detail about either statement and the article focuses more on Medvetz’s background and their courtship.

Cher dated a 22 year-old guy who worked at a bagel shop, Rob Camilletti, for several years in the 80s starting when she was 40. I thought she was married to that guy, but after consulting Wikipedia I see they were just living together. At least the guys are getting older with her. I don’t see her marrying this one, but we’ll have to see.