This looks like a photo shoot, doesn’t it? I’m not saying Olivia Wilde and Jason Sudeikis arranged to be photographed in this “Official New Couple Portraits: Loved Up On The New York City Streets Edition” way. Maybe it was just some weird coincidence. After all, people know that Jason and Olivia are dating – they’ve been seeing each other for about… two months or so. It was about a month ago when Us Weekly reported that they were a full-on couple.

Olivia spent most of the last year sowing her wild oats after her divorce from an Italian (hipster) prince. She dated Ryan Gosling, briefly, and she was associated with Bradley Cooper and Justin Timberlake too. There were other dudes in the mix, but I can’t remember them off the top of my head. It doesn’t really matter – she was just playing around, and none of it seemed serious. But this kind of photo op with Jason? That seems more serious. And I’m not sure how to feel about it.

Jason’s dating history is a bit more complicated. He was married, and the divorce dragged on for a while. While he was dealing with that, some said he and Jennifer Aniston had a fling, although Jason denied it – harshly. Then he hooked up with January Jones for a while, and they seemed to still be dating each other casually when she got knocked up – by another (married?) man, allegedly. Since January Jones, Jason has been playing the field, and Olivia might be his first “relationship” in a year.

At the end of the day, I kind of find Olivia and Jason to be a boring couple. It feels like Olivia went out, played the field, and got disappointed by the lack of opportunities, so she just settled for Jason. Maybe he’s a really nice guy… but he seems like he might have a streak of douche. Oh, well. Good luck, Cockburn.

Photos courtesy of Pacific Coast News.

Ever since Olivia “I’m a Princess!” Wilde (otherwise known as Ol’ Cockburn) left her prince husband Tao Ruspoli, she’s been out and about, hanging out with every available dude she can find. She was spotted on a date with Ryan Gosling. She and Bradley Cooper were closely associated. She might have boned Justin Timberlake at some point. And maybe Ryan Reynolds was in the mix too? I think there were others as well. Anyway, part of me kind of liked that Ol’ Cockburn didn’t jump into another serious relationship right away – she had been with the same dude since she was 18. It was time for her to experiment and get a wide variety of strange. Another part of me was like, “Oh, girl. Set some standards for the dong. Don’t just go home with any dude who needs a beard.” Well, according to Us Weekly, Olivia is settling down with a dong. And I don’t hate her choice, although I don’t think it will last:

How funny! Olivia Wilde has been romantically linked to frequent Saturday Night Live guest star Justin Timberlake, but now the In Time actress is dating a full-time cast member on the show: Jason Sudeikis!

A source tells the new Us Weekly — on stands Friday — that Wilde, 27, and Sudeikis, 36, haven’t been shy about their new romance. The SNL funnyman brought Wilde to the show’s afterparty at NYC’s Loi on Dec. 4. “They walked in holding hands,” says a source.

“She’s come to the [SNL] studio at Rockefeller Center, and they’ve gone out to dinner after rehearsals,” adds an insider.

Wilde, whose divorce with Tao Ruspoli was finalized in October, has also been romantically linked to Bradley Cooper, Ryan Gosling and Ryan Reynolds.

Sudeikis dated Mad Men’s January Jones for six months before the duo split in January 2011. He was previously married to actress and 30 Rock writer Kay Cannon.

[From Us Weekly]

I tend to think Jason Sudeikis is kind of a dick, and he’s not really “forever dong” material, but he’s good for a five-month relationship. And then she’ll want to find some new strange and he’ll want to move on to whatever new, younger piece is waiting for him. I find my perception of Jason is so skewed because he and January Jones lasted for six months and I don’t understand how any man can sustain a relationship with her cold vanilla bitchery. Is it because she’s blonde and she has big boobs? Back to Olivia – is Jason a good choice for the girl that wants to be a big movie star? Not really, but this is where Olivia finds herself now – so many of the films she was in flopped, she’s not going to “breakout” in starring roles any time soon, so why not date another supporting player? It makes sense.

Photos courtesy of WENN.

I don’t know why this Jennifer Aniston pictorial for Marie Claire is cracking me up so much. I mean, some of the photos are really lovely and flattering. I guess I’m laughing because in the cover shot, there’s something in Aniston’s crotch area that looks vaguely dongish. That’s a horrible thing to do to an actress, and totally inappropriate given the current Anthony Weiner situation. Of course, maybe it would be different if Aniston had agreed to pants?

Another reason I’m laughing is that Aniston is made to pose with her three Horrible Bosses leads, Jason Bateman, Jason Sudeikis and Charlie Day. You can tell a lot about her relationships to the men by how she poses with them, I think. With Jason Bateman, the two look genuinely close, like they’re buddies in real life (which they are) and they make each other laugh. The ones of Jen and Bateman are my favorites – she looks the most “real” and engaging, and Jason is a good-looking dude. The ones of Jennifer and Charlie Day are kind of cute too, but it seems like she’s just using him as a prop, or like she’s just trying to force the chemistry, in my opinion.

The ones with Sudeikis are the most interesting, I think. JS and Jennifer allegedly had a brief romance last year, after which Jason began dating January Jones and he seemed to laugh off the Aniston stuff. I feel like Aniston is trying too hard to make “sexy” faces and poses with Jason. In one, she’s even hiding her chin! Of course, one of the pull quotes from the magazien seems to suggest that Aniston says to Jason, “We should clear it up right now, we never dated, right, Jason?”

On the whole, I do like this shoot. I mean, it’s slightly boring and “on the nose” to promote the film, but it’s one of Aniston’s better shoots as of late. Remember that horrible Allure shoot? Yeah, this is much better.

Photos courtesy of The Fashion Spot.

January Jones is getting pap’d non-stop since she announced her pregnancy, and these are the first photos I’ve seen where her bump is visible and evident. Nice. She looks good, I think. Anyway, yesterday we heard from Jason Sudeikis, who was cornered by a WaPo reporter over the weekend. Jason basically stuttered and fumbled when asked if he was the baby-daddy, which led some (me) to believe that he was the likely inseminator. Now Us Weekly is trying to piss on that theory:

Baby brouhaha!

A source tells Us Weekly that January Jones — who revealed she was pregnant April 28 — was so intent on starting a family that it drove a wedge between her and ex-beau Jason Sudeikis.

“She told him she wanted kids and it turned him off,” says the insider of the actress, 33, and the Saturday Night Live star, 35. “Jason was bummed out she was on the mommy track.”

While Jones has yet to reveal the father of her baby, the source doubts it’s Sudeikis: “If Jason were the dad, he’d step it up.”

Mad Men producers have reportedly yet to decide whether Jones’s pregnancy will be written into the show.

[From Us Weekly]

Here’s what I get from that report: 1) Jason is an immature douche who doesn’t like women to be anything other than dumb, sexed-up kittens; 2) Since Jason and January broke up in December/January, she probably hasn’t called him to catch up or to tell him about her pregnancy; 3) If she hasn’t called him, I suspect that he isn’t the father. I get the impression that January has already told the father, and that he either doesn’t want anything to do with her, or he’ll financially support her quietly. I just get the feeling that January made her announcement when she had already informed the father, and that Jason hasn’t been informed of anything, so he’s not the dad.

In other January news, People Magazine spoke to January’s Mad Men costar Aaron Staton, who told the mag: “It’s something that she’s wanted to do and that she’s excited to do… January is such a sweet person… I think she’s an honest person. I think she’s really going to be a great mother.” Good to know!

Photos courtesy of Fame.

Life & Style is reporting that Scarlett Johansson is already moving on from her split with Ryan Reynolds, and that she went on a double date with Jason Sudeikis. Jason has been connected to a couple of high-profile women over the past year. First, it was a barely-there relationship/date with Jennifer Aniston, and then it was a longer and more extensive relationship/series of hookups with January Jones. Interestingly enough, January and Jason’s split was just “announced” last week – Jason probably did that so that when the rumors about ScarJo came out, everyone wouldn’t ask “What about January?!?” As for ScarJo… well, I always knew the girl would move on quickly. This little Sandra Bullock-Ryan Reynolds thing was a distraction from ScarJo’s new single “I’ll bone anybody!” life.

Single life is working out just fine for Scarlett Johannson! Since announcing her split with Ryan Reynolds on Dec. 14, the actress hasn’t been home dabbing her tears with a box of tissues. In fact, she’s already dating!

On Jan. 22, Life & Style spotted the newly single 26-year-old getting quite cozy with Saturday Night Live funnyman Jason Sudeikis, 35, at upscale Santa Monica pub Father’s Office. The two met Jason’s fellow SNL star Will Forte and a female guest there for burgers, fries and beer.

“It definitely looked like a double date!” an eyewitness tells Life & Style. “Scarlett and Jason were flirting and making lots of eye contact. He reached across the table twice to grab her hand.”

But Jason’s not the first guy Scarlett has been linked to since her soon-to-be ex husband filed for divorce on Dec. 23, after a little more than two years of marriage. She was the focus of many men on Jan. 8 at Jeremy Renner’s 40th-birthday party, where she was spotted flirting heavily with Entourage star Kevin Connolly and chatting up Leonardo DiCaprio. Eight days later, notorious flirter Jake Gyllenhaal even tried to woo the single gal during a CAA-sponsored Golden Globes afterparty.

Jason also seems to be licking his wounds from a recent split. As Life & Style first reported, things cooled off with one-time gal pal January Jones in December after Jason was spotted with a brunette on a double date at a New York Knicks game on Dec. 22. Jason and Scarlett got to know each other when she hosted Saturday Night Live back in November.

“Scarlett kept checking her phone like crazy,” adds the eyewitness at Father’s Office. “She was distracted, but it definitely seemed like a double date.”

A rep for Scarlett denies the couple are dating telling Life & Style, “After hosting Saturday Night Live three times, they’ve all become friends.”

[From Life & Style]

That’s interesting that ScarJo’s rep even bothered with a half-hearted denial. It’s so on. And by “on” I mean that ScarJo will bone Jason Sudeikis until something better comes along, after which she’ll be all “Jason who now?”

Photos courtesy of Fame.

Way back last year, summer of 2010. A pretty Mad Men star has her first brush with major tabloid notoriety when outlets report her involvement in a hit-and-run. January Jones only hit a tree, but she was allegedly drunk, and she walked to her home on foot, leaving the scene of the accident, returning minutes later having changed her clothes and chewing some new gum. Who shows up to support her in her hour of need? Celebrity chef Bobby Flay – the married man she had just hours before been having drinks with at a hotel bar, before they allegedly snuck off alone.

Around the same time, another rumor springs up – Jennifer Aniston has a new man, and they were conveniently spotted on a date and gossipy “sources” are all a buzz about this new guy and how he’s the new One. The rumor dies quickly, and when Jason Sudeikis is asked about in a national magazine, he quips that Aniston “should be so lucky” to date him.

Then, in a flash, January and Jason became a couple. Perhaps it was convenience. Perhaps he just prefers blondes with great racks. Perhaps she needed to change the subject after the Bobby Flay rumors. Perhaps, perhaps. Anyway, after about six months of dating, it’s over.

It’s the end of the road for January Jones and Jason Sudeikis.

The pair, who were first linked romantically last July, are calling it quits on their relationship, a source confirms to PEOPLE.

“They’ve been on and off for a few months and then the long distance kind of ended it,” the source says. “But they could get back together. It was just hard to stay together with the distance.”

Jones, who stars on Mad Men is based in Los Angeles, where AMC’s hit period drama is filmed. Sudeikis is part of the ensemble cast that puts on NBC’s Saturday Night Live, which films in New York City.

[From People]

While I thought they were “meh” as a couple, I would have liked to see more of them out and about together. When I saw that January seemed to be flying solo at the Globes on Sunday, I had a brief moment of “I wonder why Jason isn’t with her” but I just figured he probably couldn’t get away from SNL. Anyway, it probably was just a PR hookup, something convenient for both of them to change the subject from Bobby Flay and Jennifer Aniston. Plus, I mean, January is a pretty blonde with big boobs and Jason probably loved that about her. She’s also dumb as a rock. Like, intensely stupid. So maybe we shouldn’t over-think this. She isn’t.

Photos courtesy of Fame.

My goodness! In the wake of Radar’s scoop that Jennifer Aniston went on a flirty, hair-touchy date with Lindsay Lohan’s ex, 29-year-old Pink Taco dude Harry Morton, there have been a number of strategic leaks about Aniston’s “dates”. I don’t know if any of this is true, but I do know that someone out there is pushing the “Aniston is juggling lots of different men” story pretty hard. So, first there was Harry Morton – that was on Wednesday, I believe. Here’s a vintage photo of Harry when he was with Lindsay Lohan:

And now it looks like Aniston had another date with another dude on Thursday night. Two dates with two guys in two days? Oh, Aniston. I mean, good for her…? Anyway, TMZ announced that she went out with Cougar Town actor Josh Hopkins Thursday night – they even have photos of the two of them in his car, Aniston riding shotgun (hopefully that wasn’t the only thing she was riding). TMZ has the photo and story here – Aniston and Hopkins went to Madeo, which I believe is the same place Ashton Kutcher was allegedly screwing around on Demi Moore, correct? BUT! E! News claims that Aniston was in fact with Christopher Gartin, the divorced father who she maybe homewrecked.

Jennifer Aniston is not one to be photographed with Lindsay Lohan’s leftovers and let the story sit around too long. After dining with LiLo ex Harry Morton Wednesday at The Sunset Tower Hotel, Jen was papped last night having a romantic dinner date at Madeo in West Hollywood with another familiar gentleman.

So who’s the guy? None other than rumored boyfriend (‘tho we just think more-than-friend) Chris Gartin. Jen and Chris enjoyed a three-hour dinner at Madeo, where onlookers tell us they very much looked like a couple.

“They were on a date,” says a fellow diner. “She was all cozied up to him and they were talking closely and laughing.”

Our source says the two arrived at about 7:30 p.m. and sat at a table secluded from the main dining area. When they left around 10:30 p.m., our source says the two covered themselves with a sheet in their chauffeured car to avoid the snaps of the 15-plus paparazzi waiting outside.

But this isn’t the first time these two have been spotted out together. Chris, 42, and Aniston, 41, were seen on two dinner dates earlier this summer, one at Soho House West Hollywood and another at Jen’s favorite hang, Sunset Tower, in July.

So what exactly do we know about Gartin? Well, he’s also a friend of David Arquette and Courteney Cox, and he’s got a True Blood connection (so Jen, we may really be getting on board with your latest fling choice). So what’s up with these two? We asked Gartin’s rep, and have yet to hear word one. However, back in July, Chris’ rep told E!, “No comment.”

We don’t think these two are bf-gf status yet, but he’s cute Jen, no harm in a last minute summer fling!

[From E! News]

But if TMZ has a photo of her leaving with the CougarTown dude, does that mean the Gartin stuff is all bullsh-t? I don’t know. I really don’t. Here are photos of Josh Hopkins and Christopher Gartin:

There’s yet another story about a dude that Aniston may or may not have boned – remember those stories about her and SNL’s Jason Sudeikis? There were allegedly seeing each other several months ago, although Aniston’s rep denied it and Jason told GQ “she should be so lucky” to date him. Well, Jason got some Aniston questions in his Vanity Fair profile, and he had some interesting stuff to say – the full Vanity Fair piece is here, and it’s totally worth a read, but here are the relevant highlights:

Jason on “older women” (the interviewer’s words) treating him differently when he has a mustache: “They responded to it more. I don’t have any specific stories about it, like Helen Mirren hitting on me or anything. But they just looked at me differently. And younger girls definitely didn’t like it. It was really interesting getting to know people for the first time when I had the mustache. Jennifer Aniston only knew me with a mustache, so when I saw her again after I shaved it, like a month or so later at a screening, it was surreal. A mustache really defines your face.”

You’re working on Horrible Bosses right now with Aniston and Jason Bateman. Word is that it’s going to be rated R, and it’s a hard R. Does everyone in the cast get naked in this thing?
I don’t even know. There must be some nudity, but I don’t know who it is. I guess we’ll all find out at the Cannes premiere. I know who everybody’s hoping it is.

You can’t confirm or deny Aniston’s nudity?
I can’t. All I can tell you is that I won’t be naked. It’s in my nudity riders. I’m only allowed to show the middle of my dick.

A hilariously bad joke about The Girl With the Dragon Tattoo: “No, [I don’t have anything] too bad [on my body]. It’d be hilarious, though, if I had something like what that guy had tattooed on his stomach in Girl With the Dragon Tattoo. Did you read that book? I forget what his tattoo said, but it was something awful like “I’m a pig and a rapist.” But, come on, how bad can that be, really? I mean yeah, he has that tattoo for the rest of his life, but all he has to do is add “JKLOL” at the bottom and everybody will think it was just a joke.

If the tabloids are to be believed, you’ve apparently been juggling steamy affairs with Jennifer Aniston and January Jones. Is that something you even pay attention to?
I completely pay attention when I’m sleeping with someone. It’s one of the things I’m known for. I’m always super focused on it. Knowing their name, knowing if something’s working. You will never hear otherwise.

Let’s cut to the chase. Why did you break Jennifer Aniston’s heart?
(Very seriously.) I don’t know, I don’t know. Bad manners maybe? (Laughs.) You know the worst part? Even joking about it gets taken out of context. It’s such a weird thing to even speak about. I make what I think is clearly a joke and then some people… (Sighs.) I don’t know, it’s hard. I guess it just proves that not everybody has the same sense of humor as I do. I try not to be too worried about it.

Because of all the media scrutiny, are you more protective of your relationship with January Jones?
I don’t know what there is to be protective about. We’re dating, she’s great. I’m very happy with everything.

January plays Betty Draper on Mad Men. At least until recently, your Saturday Night Live castmate Fred Armisen was married to Elisabeth Moss, who’s also on Mad Men. What’s the deal with all the sexual chemistry between S.N.L. and Mad Men?
I feel like it all started with 30 Rock, when Jon Hamm dated Liz Lemon. That trail was blazed long ago, long before I met January.

That’s a very diplomatic way of putting it.
(Laughs.)I don’t know, man. It’s just a mess. It’s like an orgy made in Entertainment Weekly heaven.

[From Vanity Fair]

What does it all MEAN? Eh. Here’s my interpretation of it: Jason and Jennifer had some sexual chemistry and they went on a date and nothing came of it, and Jason moved on to January Jones who he is very happy with. And now when he gets questions about Aniston, he doesn’t really know what to say, but he tries to be a gentleman and ends up making awkward jokes. That’s how I interpret it, but I’m sure there will be other takes. Also: Jason confirms something that warmed my heart: both times Jon Hamm hosted SNL, My Hamm gave each person their own bottle of Maker’s Mark. Isn’t that sweet?

Oh, snap! Jason Sudeikis has a little interview in the new issue of GQ Magazine, and when he’s asked about those rumors (a few months ago) that he was dating Jennifer Aniston, he replies “She should be so lucky.” Just joking around? Or is there some sort of dirt? I have no idea. Maybe he just has his eye on keeping everything low-key with January Jones. Here’s more from GQ:

Occupation: SNL player

Age: 34

Credits: Five seasons (and counting) on Saturday Night Live; comic relief in this month’s Going the Distance, with Drew Barrymore; voices the hipster Holt Richter on The Cleveland Show

Summer plans: Filming Horrible Bosses with Jennifer Aniston

On rumors he’s dating Aniston: A pause, followed by laughter. “She should be so lucky.”

Strangest SNL moment: “Hearing Don Pardo say your name.”

Comedy role models: “When I’m doing something funny, in that moment I sometimes think, I’ve ripped off either Chevy Chase, Eddie Murphy, or Ellen DeGeneres.”

On Ellen DeGeneres: “I’m dead serious—she’s my Justin Timberlake. I had a crush on her. Still do.”

Growing a mustache for Going the Distance: “The mustache draws a line in the sand. I’d walk by women who would dart their eyes away immediately. Depending on what neighborhood you’re in, some guys’ eyes would linger.”

Celebrity trivia, part 1: He and Paul Rudd went to the same high school in Kansas.

Celebrity trivia, part 2: His uncle is George Wendt, a.k.a. Norm from Cheers.

Best advice from his uncle: “Get on one of the best sitcoms ever and then ride it out.”

What’s never not funny: “Farts.”

[From GQ]

The more I see or read about this guy, I’m actually thinking he comes across as very cocky. That works on some men, but on Jason Sudeikis? Eh. Yes, he’s cute and talented. But a little humility, maybe?

Jason Sudeikis photos courtesy of GQ. Aniston on July 20, in London. Credit: Bauer-Griffin.

Both Jason Sudeikis and January Jones have been making the wrong kinds of PR moves for the past few months, so it’s not surprising that they would find each other and somehow try to overcome this junk by having private hot sex and public photo ops. I think January’s case is worse – after being linked to two Lords of the Douche (Adrien Brody and Jeremy Piven), January then seemed to have some kind of drunken affair with a very married man – chef Bobby Flay, who came to her rescue when her (allegedly) drunk ass plowed into some cars. Jason, on the other hand, was rumored to be dating Jennifer Aniston for about a minute, until the tabloids dug up some dirt on him and found that he’s a player with a history of romancing and dumping women.

So is this a case of the dirt bag meeting the homewrecker? Eh. I still like them both, even though I think January might have some serious issues with men. Jason – well, maybe he just needs to find the right girl. Maybe a pretty, buxom blonde from Nebraska? Perhaps.

Ooh, I think they met at the ESPYs? They were both there last week – damn, January moves fast! Here are the photos of them (separately) at the ESPYs:

January and Jason on July 18, 2010. Credit: Fame.

The tabloids are chock full of stories about Jennifer Aniston’s alleged relationship with Jason Sudeikis. The rumors started last week when a British tabloid reported that Aniston and Sudeikis had gotten involved right after his divorce. Unfortunately, Aniston’s rep just denied this sh-t:

Stop the gossip: Jennifer Aniston isn’t heating up with one of her costars in The Bounty Hunter.

“She is not dating Jason Sudekis,” her rep tells UsMagazine.com.

Sudekis, 34, divorced wife, 30 Rock writer Kay Cannon, earlier this year.

Still, Aniston’s rep adds, “I have no idea how this rumor got started, but there is no truth to it whatsoever.”

On Tuesday, Aniston helped BFF Courteney Cox celebrate her 45th birthday at Bouchon Beverly Hills.

“The group sang ‘Happy Birthday’ to Courteney,” a witness tells Us. “They all seemed to be laughing and having a great time.”

[From Us Weekly]

I wonder what happened? Do you think Aniston and Sudeikis were never dating, or they were and it’s over, or they were and are, and they just want it quiet? Secret hidden option four: Jason was a candidate for Aniston to fake-date, and it didn’t work out so Aniston is cutting him loose. Just putting it out there.

I’m a little disappointed, because I was looking forward to talking about the other tabloid rumors about Jason and Jennifer. It was getting juicy! OK Magazine (via Jezebel) is claiming that Aniston liked Jason’s “wicked, dry wit” and that “she’s missed being with an intellectual.” You mean John Mayer wasn’t an intellectual? Also, In Touch Weekly claims that Jennifer was the reason Jason got a part in Horrible Bosses, and that “she wouldn’t have pushed for him to get the part unless she saw a future with him.” Also, Jason is a cheater? When his marriage started having problems, he maybe had a bunch of girls on the side. Oh, and In Touch insinuates that Aniston and Sudeikis have Skype sex. Oh well. Lost another one.

Aniston on March 30, 2010. Credit: WENN.