Two months ago, Jake was spotted having an intimate lunch with Rashida Jones and snuggling up to Anna Kendrick on the same weekend… but now, it seems the actor has set his sights on “In Time” actress Olivia Wilde.

Olivia and Jake were spotted having dinner with a group of people at Chinatown Brassiere. Though the outing was hardly intimate, the two were reportedly seated next to each other and—and they looked “very cozy.”

An eyewitness revealed to Page Six:

“They were in a group but were very cozy with their chairs pulled in closely together.”

This isn’t the first time Olivia and Jake were spotted out together. Earlier this year, the twosome was seen together at Chateau Marmont in Los Angeles—although at the time Wilde’s rep claimed that they were “just friends.”

What do you think of Olivia and Jake as a couple?

images via WENN

Jake’s quite the ladies’ man, isn’t he?

It’s official—Jake Gyllenhaal definitely had an eventful weekend. The actor was first seen hanging out with Rashida Jones at a café in Los Angeles, then later with his “End of Watch” co-star, Anna Kendrick.

Jake was photographed hugging it out with Anna after grabbing some sandwiches with the rest of the “End of Watch” crew during Labor Day weekend.

So yeah. Two girls in one weekend. Kind of confusing, isn’t it?

Anyway, since both girls are brunettes, we’re guessing Jake’s gone cold turkey on his “blonde addiction” (Kirsten Dunst, Reese Witherspoon, and Taylor Swift).

Who do you think Jake’s really seeing?

images via WENN

Jake and Rashida reportedly had lunch together and spent the entire afternoon together at the Cafe Gratitude on Sunday. As they were leaving, onlookers saw Rashida playing with Jake’s puppy, Atticus, who was outside the café waiting for them.

According to celebrity news, the newly bald actor was spotted earlier this week at a movie theater with an unidentified friend. The actor and his companion watched French thriller “Point Blank,” and then reportedly tried to remain incognito as they left the theater.

Could Rashida be Jake’s mystery movie friend? Quite possible.

Do you think they make a cute couple?

images via WENN

Jake and Michael were on a ride-along with the LAPD cops—research for their new movie ‘End of Watch‘—when they were called to the bloody scene.

The two discovered the injured man, who sustained grazing bullet wounds on his lip and arm after being shot by gang members. The victim was brought to the hospital soon after and is now in stable condition.

Jake’s new movie (which he went bald for), ‘End of Watch’, is a cop drama that follows the long-term friendship between two police officers. The film will hit theaters in July.

After their discovery, we’re betting Jake and Michael are REALLY glad they chose acting as a profession.

image via WENN

According to the singer, the song is dedicated to all of her critics—the ones who have nothing but negative things to say about her music. However, the latest Hollywood gossip is that the song is actually about her ex, Jake. The video itself seems to be chock-full of metaphors about not-so-peachy relationships—particularly a scene that shows Taylor tied to train tracks by a horrible (male) villain while she sings:

“You, with your switching sides,

And your walk by lies and your humiliation

You, have pointed out my flaws again,

As if I don’t already see them.

I walk with my head down,

Trying to block you out cause I’ll never impress you

I just wanna feel okay again.”

Now let’s do a little reading-between-the-lines here. Could the first line be about Jake’s rumored romantic connection to Joe Jonas’s ex-girlfriend, Camilla Belle? And what about the next few lines? Is Taylor saying that she never felt good enough for Jake because he always made her feel inadequate?

image via WENN

Jake was recently photographed on the set of his new film, ‘End of Watch’, sporting a completely shaved head. According to the actor’s rep, Jake shaved his head for his role as a devoted cop in his new movie.

Of course we can all agree that Jake Gyllenhaal looks good with or without hair, and we’re sure his dating life won’t suffer one bit.

Check out the picture of Jake’s new bald hairstyle and tell us what you think! Does Jake Gyllenhaal look better with a shaved head?

image via WENN

Guess Gyllenhaal,30, is testing the water and keeping his romance options open!

We reported earlier this week that Gyllenhaal was seen having lunch with a Taylor Swift look-alike on April 3 at NYC’s Locanda Verde. And we did suggest that Jake should start dating a brunette.. there you go!

Do you think Gyllenhaal and Lowndes,22, make a hot couple?

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According to an eye-witness:

“It was a casual meeting in the back corner booth. They were laughing and enjoying each other’s company.”

The witness then goes onto say Jakey was being very animated and it appeared as if he was working very hard to impress his lady friend.

Well, well! If it doesn’t work out, perhaps he should try dating a brunette next?

Photos: WENN

The story centers on a soldier (played by Gyllenhaal) who wakes up in the body of an unknown man and discovers he’s part of a mission to find the bomber of a Chicago commuter train.

Other Jake news if you’d missed, the hottie (I somewhat think Jake is pretty hot these days must be all the exercise he’s been doing) got into a bathroom brawl with some guy who was trying to take a picture of him. LOL. Well, you can’t blame Jake if he did get upset, can you?

The movie hits theaters on April 1st.

images via WENN

Jake was out over the weekend and a fan took a picture of Jake while he was doing his thing. Not so cool.

EW: There are rumors that there was a rather heated scuffle in the theater bathroom last night as a fan tried to take your picture at an inelegant time?

JG: (laughs) That’s true. I think it’s an appropriate space to keep privacy. I hope that people wouldn’t disagree with me on that.

Seriously, while he was taking a bathroom break? I guess it’s true that they live a public life! Jake said he didn’t punch him, but talked him in to deleting the picture. What do you think really happened?

Photos via WENN

He told the magazine:

“I’ve had to teach myself to slow down a bit. Because I get so into it, it becomes a real addiction. But it’s like a New Year’s resolution – to sit down and read a book. Life’s not a bike ride. I wouldn’t say exercise less, but sit with myself.”

Wonder if he had to go through a 12-step program…

Photos: WENN

To celebrate Aniston‘s 42nd birthday last night she and group of friend’s met for dinner The Spotted Pig, a popular New York City eatery.

“Jake and Jen looked really happy and really seemed to be enjoying themselves,” an eyewitness tells the Scene Queens. “They looked like they were strategizing a way to exit the restaurant probably because they didn’t want to be photographed together.”

Yeah, so basically Jake showed up to Aniston’s party, ate and had a good time and then left out the backdoor. How Life and Style ever managed to assume they were sleeping together is beyond me, but this would make an excellent tabloid cover, no?

Photos: WENN

After splitting in late December, Taylor Swift is still torn up inside after another failed romance. A friend of hers told Popeater.com:

“Taylor is not exactly a loner, but she fares well on her own and will be fine if she doesn’t hook up with a guy immediately.”

According to several reports, Swift hasn’t recovered from the breakup and isn’t her usual bubbly self. If anything, she’s busy in the studio working on her breakup song.

Oh, yes. America is waiting for the epic Jake Gyllenhaal break-up song! Her songs are a better than a gossip tabloid story!

Photos: Fame

They were an item back in 2001 but they are just good friends as the buzz goes. But what’s with Camilla?

“They hung out together the entire night,” an eyewitness tells Radar Online. “They were talking intimately, and laughing. There really seemed to be chemistry, a connection.”

Art of Elysium is one of Hollywood’s favorite charities. It takes the arts to children battling life-threatening illnesses in hospitals and rehab centers.

“Jake and Camilla were flirting all night,” the source says. “And before he left, I saw him very affectionately touching her arm.” “She is definitely his type.”

Jake, 30, and Camilla, 24, already share something in common. Camilla dated Joe Jonas who also dated Taylor Swift. Oh it’s a small world in Tinseltown!

Do you see Jake and Camilla dating? I so see them together! I think they would look really hot, don’t you?

photos: Fame

In fact, it seems Jakey called all the shots, got tired of her, and dropped her like last week’s news.

“It was a 180-degree turn and so out of the blue. Jake just told her it wasn’t working out…Taylor is really upset and hurt. She doesn’t know what she did for him to put a stop to it. She feels really burned by him. Jake started this whole thing, but then he just stopped responding to her.”

Get used to it, Swifty! But, seriously, do you really think she’s upset about this or is it all a publicity stunt to boost her album sales and create some sort of alliance with heartbroken teenagers?

Photos: Fame

“Jake reached out to her and started all of this, but now he’s not acting as interested,” a source tells Us Weekly (on stands today, Wednesday).

“He said he wasn’t feeling it anymore and was uncomfortable with all the attention they got,” says the insider. “He also said he could feel the age difference. Taylor is really upset. We told her not to move so fast with this but she didn’t listen.”

Explains a Gyllenhaal insider, “Jake cares about her, but [the publicity] was a lot for him. He wants to keep his private life private, and that’s hard to do dating Taylor.”

Jake and Taylor dated for about two months before calling it quits right before New Year’s Eve and rang in 2011 separately.

Looks like Taylor, 21, could be buzy penning her next break-up song. Good luck to you Jake.

Back on the drawing board. Who should Jake date next? I suggested Mila Kunis when the break up news first surfaced yesterday. Do you see Jake and Mila as a couple? I think they will make a really hot couple, don’t you?

Who should Taylor date next? That’s a tough call.

photos: Fame

Taylor turned 21 on Dec 18 and Jake, 30, on Dec 19.

“They’re over,” a source tells PEOPLE. “It ended last month.”

Swift rang in 2011 solo at a party in Nashville while Gyllenhaal was in New York where he attended a closing party for Broadway’s Fela! on Jan. 2. He also dined with his mother while in the Big Apple.

They two were last seen together in Los Angeles on December 9th.

That was brief! Oh well back to the drawing board. Who should Taylor date next? What about Jake? Oh Jake how about pursuing Mila Kunis? She’s beautiful and available.

photos: Jake with Love and Other Drugs’ co-star Anne Hathaway

photos: Fame

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photo: Fame

The pair Jake and Taylor dined together at Gwyneth’s home in London. Gwyneth told USA Today when asked if she had set up the new couple, “I’ve just known Jake for a long time and he’s a great guy, and Chris has a friendship with Taylor.”

Given how much Taylor and Jake enjoy being together, I think they should be thankful to Gwyneth’s good job for bringing them together!

Do you see Jake and Taylor staying together for a long time?

photos: Fame

Not for high-balling Jake Gyllenhaal:

“And it wasn’t just any old guitar; Jake had clearly put a lot of thought into what kind of guitar his country singing girlfriend might want. As a result, Taylor received a vintage Gretsch guitar signed by country star Chet Atkins from her new man. According to reports, Jake got the hot hint about the special instrument when Taylor reportedly gushed about Gretsch during a recent trip to Nashville.”

Do you think Jake and Taylor will make it and be together for years?

Photos: Fame