Jake Gyllenhaal


Jake Gyllenhaal and Alyssa Miller out and about in Tribeca, Manhattan (9/23)

Jake Gyllenhaal is somehow still dating ridiculously hot supermodel Alyssa Miller. That's the two of them out in Manhattan earlier this week. Thank god for acting because guys like Jake simply don't pull ass like that in the real world. Usually it's the first spider that does them in. "Eeeeeeek! Someone kill it!" *flaps hands up and down in the most effeminate way possible*

*10 Jake Gyllenhaal pictures total in the gallery:

  • Jake Gyllenhaal Hot Girlfriend
  • Alyssa Miller Good Looks
  • Jake Gyllenhaal Dating Supermodel
  • Alyssa Miller Upskirt Dress
  • Jake Gyllenhaal Engaged to Alyssa Miller
  • Alyssa Miller Fuck Me Boots
  • Alyssa Miller Tall Model
  • Jake Gyllenhaal Sexy Girlfriend
  • Alyssa Miller Boyfriend Pics
  • Jake Gyllenhaal Proposes to Alyssa Miller

Jake Gyllenhaal and Alyssa Miller in New York (7/15)

Here's the first pics of Jake Gyllenhaal and his rumored new girlfriend, supermodel Alyssa Miller. So I guess it's pretty much confirmed that they're dating. I know, right? A handsome, wealthy actor hooks up with a drop dead gorgeous supermodel. What a crazy turn of events. What's next, a white president?

*10 Jake Gyllenhaal and Alyssa Miller pictures total in the gallery:

  • Jake Gyllenhaal With Alyssa Miller 1
  • Jake Gyllenhaal With Alyssa Miller 2
  • Jake Gyllenhaal With Alyssa Miller 3
  • Jake Gyllenhaal With Alyssa Miller 4
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Jake Gyllenhaal's new girlfriend Alyssa Miller

After being linked with the gorgeous Emily DiDonato earlier this year, Jake Gyllenhaal is now dating the equally gorgeous Alyssa Miller. I bet she has a great personality. From the New York Post:
Jake Gyllenhaal has traded in his girlfriend for a new model. Sources say he's moved on from Sports Illustrated Swimsuit babe Emily DiDonato to another SI stunner, Alyssa Miller. Spies tell us that Gyllenhaal and Miller were spotted at lunch last week at the Dutch in Soho before reports they'd been "making out" at Cold Process Coffee & Tea. Gyllenhaal dated DiDonato for "a month or two," according to reports. Reps for Miller and Gyllenhaal declined to comment.
Just to show you guys that I'm not a one-trick pony, I'm not gonna pinch a loaf on Jake today. Why should I? Running though Victoria's Secret models is his right as an entertainer and as an American citizen. And I also consider it a kind of penance for starring in one of the most vile, American culture-hating movies of all time: Bubble Boy (this is reason why beheadings should never be taken off the table as a legitimate movie review). Good for Jake. He really needs to plow his way through runway models to show why Minka Kelly should take him out of the friend zone. You remember something, Jake Twist, the only way to hook up with the one you want is by showing that you DON'T need her (or him).

*30 Alyssa Miller pictures total in the gallery:

  • Alyssa Miller Dating Jake Gyllenhaal
  • Alyssa Miller Leaning on a Tree
  • Alyssa Miller Sexy Long Legs
  • Alyssa Miller See Through to Nipples
  • Jake Gyllenhaal Dating Alyssa Miller
  • Alyssa Miller in a purple bikini
  • Jake Gyllenhaal Dating Swimsuit Model
  • Alyssa Miller Gorgeous Brunette Hair
  • Alyssa Miller Bikini Photoshoot
  • Jake Gyllenhaal Dating Bikini Model
  • Alyssa Miller in Underwear
  • Alyssa Miller Swimsuit Issue
  • Alyssa Miller Colorful Bikini
  • Alyssa Miller in Lingerie
  • Alyssa Miller Half Naked
  • Alyssa Miller Bright Green Swimsuit
  • Alyssa Miller in Sunglasses
  • Jake Gyllenhaal New Girlfriend
  • Alyssa Miller Bikini Tits
  • Alyssa Miller in a swimsuit
  • Alyssa Miller Almost Nude
  • Alyssa Miller Wearing a Bra
  • Alyssa Miller So Hot
  • Alyssa Miller Laying on the Beach
  • Alyssa Miller NSFW
  • Dream girl Alyssa Miller
  • Alyssa Miller Bikini Bottoms
  • Alyssa Miller Sexy Photoshoot
  • Alyssa Miller in Red Lingerie
  • Alyssa Miller Nice Tits

Emily DiDonato in her work uniform

Us Weekly says Jake Gyllenhaal is dating 22-year-old model Emily DiDonato. An older actor dating a younger model, you say? Why I simply won't believe it until I see it with my very eyes!
A source tells Us that Gyllenhaal, 32, met the 22-year-old stunner in a spin class at a SoulCycle in Manhattan last fall. The actor and DiDonato (who was featured in Sports Illustrated's 2013 swimsuit issue) have dated for "a month or two," adds the insider.

It's no surprise the star found his sweetie at the chic studio, where he works out weekly whenever he's in NYC. Says a source, "He'll hop on the instructor bike. He loves the attention from the girls!"
Jake's lucky he got to Emily before I did. I was actually gonna hook up with her after one of our spin classes, but then I remembered that I'm not gay and I don't take spin classes. Dork.

*30 Emily DiDonato pictures total in the gallery:

  • Emily Didonato Jake Gyllenhaal 1
  • Emily Didonato Jake Gyllenhaal 2
  • Emily Didonato Jake Gyllenhaal 3
  • Emily Didonato Jake Gyllenhaal 4
  • Emily Didonato Jake Gyllenhaal 5
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  • Emily Didonato Jake Gyllenhaal 30

Katie Holmes out and about in New York (12/30)

According to The Sun, Katie Holmes has been secretly dating Jake Gyllenhall for the past few weeks. If he's a hopeless romantic like me, he's probably already taken her to Olive Garden, like, twice. A source told the tabloid:
"[Katie's ex Joshua Jackson] has been the mastermind behind this romance. Katie says that they have tons in common and Jake has already been to see her in Dead Accounts, plus she has been over to his apartment in the West Village for dinner."
Wise move by Jake catching Katie on the rebound and moving right into Tom Cruise's old space (the separate bedroom down the hall with the single bed), if you catch my drift. In fact, I'm sure Jake reminds Katie a lot of Tom, hint hint. Lotta vacant closet space for someone like Jake in Katie's New York apartment, if you know what I'm saying. I'm sure a "bachelor" like Jake cou-COCK. HE LIKES COCK.

*25 Katie Holmes pictures total in the gallery:

  • Katie Holmes Jake Gyllenhaal Dating 1
  • Katie Holmes Jake Gyllenhaal Dating 2
  • Katie Holmes Jake Gyllenhaal Dating 3
  • Katie Holmes Jake Gyllenhaal Dating 4
  • Katie Holmes Jake Gyllenhaal Dating 5
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  • Katie Holmes Jake Gyllenhaal Dating 25

Minka Kelly denied Jake Gyllenhaal

Jake Gyllenhaal wanted a piece of the sweet sweet ass that is Minka Kelly, but he got shot down faster than Col. Nakesh's MIG in Iron Eagle. Fucking LOVE that movie! From Us Weekly:
Minka Kelly "declined" an invitation from Jake Gyllenhaal when he asked her on a date last fall, a source tells the new issue of Us Weekly. But it wasn't because Gyllenhaal didn't measure up. At the time, Kelly had split with her on-and-off beau, Derek Jeter, and "was trying to patch things up," the source explains. Kelly's willpower paid off: She reconciled with Jeter in December.
Really? Come on, Jake. If you're reaching for The Captain's table scraps, you should probably work on that resume.  Sure, you were great in Donnie Darko and the gay cowboy movie, but you have Bubble Boy and Prince of Persia under your belt, too. Work on it. Oh BTW, I checked your Wikipedia page. You are what we MMA fighters call a pussy. Minka doesn't want a girlie-man to plant trees and meditate with all day long. What Minka needs is the relentless pelvis-pounding that only we athletes can deliver. That's what Jeter delivers, it's what I deliver, and that's all there is to it, little man.

*25 Minka Kelly pictures total in the gallery:

  • Minka Kelly Jake Gyllenhaal 1
  • Minka Kelly Jake Gyllenhaal 2
  • Minka Kelly Jake Gyllenhaal 3
  • Minka Kelly Jake Gyllenhaal 4
  • Minka Kelly Jake Gyllenhaal 5
  • Minka Kelly Jake Gyllenhaal 6
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  • Minka Kelly Jake Gyllenhaal 22
  • Minka Kelly Jake Gyllenhaal 23
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  • Minka Kelly Jake Gyllenhaal 25

A dream scenario for Jake Gyllenhaal

I have a feeling Jake Gyllenhaal has had many a dream about this exact scenario . . . from the New York Post:
Jake Gyllenhaal had hoped for a nice, relaxing steam when he turned up at the 10th Street baths last week -- but arrived to find the place packed with power players in robes. Organizers of Elit by Stoli’s male-only gathering had taken over the place, with white towel-wearing guests including Nobu’s Richie Notar, venture capitalist Adam Dell, Niche Media founder Jason Binn, David Rabin and Lance Broumand. We’re told they, ahem, “let it all hang out.”
Oh no, Jake must have been disgusted to be surrounded by those nude men . . . especially since he usually doesn't take his clothes off at home unless there's at least double that many. No, what really must have upset Jake was the setting. How's a guy supposed to get a good look at another guy's junk with all of that steam blurring his vision? If Jake barely wanted to see all the naked men he was surrounded by because his vision was hazy, he'd switch places with Lindsay Lohan.

*11 Jake Gyllenhaal pictures total in the gallery:

  • Jake Gyllenhaal Bath 1
  • Jake Gyllenhaal Bath 2
  • Jake Gyllenhaal Bath 3
  • Jake Gyllenhaal Bath 4
  • Jake Gyllenhaal Bath 5
  • Jake Gyllenhaal Bath 6
  • Jake Gyllenhaal Bath 7
  • Jake Gyllenhaal Bath 8
  • Jake Gyllenhaal Bath 9
  • Jake Gyllenhaal Bath 10

Jennifer Aniston leaving Good Morning America studios in New York (2/10)

Is Jake Gyllenhaal nailing Jennifer Aniston? You better believe there's a chance possibly, brother! From Life & Style:
Life & Style’s Scene Queens can exclusively reveal that Jennifer Aniston celebrated her 42nd birthday on Feb. 11 by having an intimate dinner with Jake Gyllenhaal in NYC.

The startlet took a break from her whirlwind promotional tour for her new film Just Go With It and made her way to The Spotted Pig restaurant where she dined in a private room with a group of friends and her former hunky co-star. “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.” Shortly after their discussion Jen exited the restaurant with her friends in tow.

“Jen and Jake looked very comfortable with each other,” the eyewitness tells the Scene Queens. “They were glowing.”
Obviously these two aren't going out. No guy in his right mind would dump a 21-year-old (Taylor Swift) for a 42-year-old (Aniston). That'd be like downgrading from a Ferrari to a Pinto, broadband to dial-up, or internet porn to magazines. Once you've had one, you just can't go back to the other. Besides, at her age, there's only one reason why a guy might want to date Jennifer Aniston: her experience enthralling stories about how she used to buy bread for a nickel.

*12 Jennifer Aniston pictures total in the gallery:

  • Jake Gyllenhaal Jennifer Aniston 1
  • Jake Gyllenhaal Jennifer Aniston 2
  • Jake Gyllenhaal Jennifer Aniston 3
  • Jake Gyllenhaal Jennifer Aniston 4
  • Jake Gyllenhaal Jennifer Aniston 5
  • Jake Gyllenhaal Jennifer Aniston 6
  • Jake Gyllenhaal Jennifer Aniston 7
  • Jake Gyllenhaal Jennifer Aniston 8
  • Jake Gyllenhaal Jennifer Aniston 9
  • Jake Gyllenhaal Jennifer Aniston 10

Jake Gyllenhaal at the "2011 Palm Springs International Film Festival Awards Gala" at the Palm Springs Convention Center (1/8)

Turns out it was Jake Gyllenhaal who dumped Taylor Swift and not the other way around, as most straight guys assumed. From the Chicago Sun Times:
Gyllenhaal quickly realized the duo had little in common, and he was fast becoming bored with the pop superstar.

“They are only nine years apart in age [Jake just hit 30; Taylor nrecently turned 21], but at their ages, those nine years are more significant than they would be a few years down the road,” said a music executive who knows Swift well.

A Gyllenhaal friend in New York added, “While Jake should have realized him dating Taylor would make them as much of a magnet for the media as when he was with Reese [Witherspoon], somehow that didn’t click with him until they were already going out."
What's Jake's problem? I thought the whole reason guys want to become famous is so they can bang chicks younger than them. If Jake really wants to go out with someone more age appropriate, he should move away from Hollywood and live somewhere where wealthy/successful men are forced to date women their own age: Puritan New England Hell.

*17 Jake Gyllenhaal pictures total in the gallery:

  • Jake Gyllenhaal Palm Springs 1
  • Jake Gyllenhaal Palm Springs 2
  • Jake Gyllenhaal Palm Springs 3
  • Jake Gyllenhaal Palm Springs 4
  • Jake Gyllenhaal Palm Springs 5
  • Jake Gyllenhaal Palm Springs 1
  • Jake Gyllenhaal Palm Springs 2
  • Jake Gyllenhaal Palm Springs 3
  • Jake Gyllenhaal Palm Springs 4
  • Jake Gyllenhaal Palm Springs 5
  • Jake Gyllenhaal Palm Springs 6
  • Jake Gyllenhaal Palm Springs 7
  • Jake Gyllenhaal Palm Springs 8
  • Jake Gyllenhaal Palm Springs 9
  • Jake Gyllenhaal Palm Springs 10

Rachel Bilson at Fashion Week in New York (9/10)

Seems like a good way to silence gay rumors would be to start nailing the impossibly-cute Rachel Bilson. Good job Jake Gyllenhaal. From the San Francisco Chronicle:
Jake Gyllenhaal and Rachel Bilson are reportedly a couple, according to new romance reports. Gyllenhaal, who has dated Reese Witherspoon and Kirsten Dunst, and Bilson, who recently split from fiance Hayden Christensen, are an item, according to HollyScoop.com. A source close to the couple tells the website, "They're trying to keep a low profile but they're definitely dating."
This is fantastic news -- now I'll be able to rest a little easier knowing that these two have found each other. For a moment there, I was actually worried that two good-looking, multimillionaire celebrities in the prime of their careers might never be able to find happiness. It just goes to show you that if you're patient, there's someone special out there for everyone -- as long as you're rich, famous, and under 30.

*25 Rachel Bilson pictures total in the gallery:

  • Rachel Bilson Jake Gyllenhaal 1
  • Rachel Bilson Jake Gyllenhaal 2
  • Rachel Bilson Jake Gyllenhaal 3
  • Rachel Bilson Jake Gyllenhaal 4
  • Rachel Bilson Jake Gyllenhaal 5
  • Rachel Bilson Jake Gyllenhaal 1
  • Rachel Bilson Jake Gyllenhaal 2
  • Rachel Bilson Jake Gyllenhaal 3
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  • Rachel Bilson Jake Gyllenhaal 5
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  • Rachel Bilson Jake Gyllenhaal 20

Would You Rather?

Would You Rather...? Spend one night with: