Kirsten, Jennifer, Selma, etc.

Seeing Jennifer Aniston and Kirsten together I wondered briefly whom Jake really had more chemistry, and I say briefly because although Jake and Kirsten were actually an official couple: it's undeniable how much comfortable Jake has always seemed to be in company of Jen:
And with Selma Blair, these recent additions to the Iheartjake gallery prove there is also sparks between them, don't you think? If not, read this old interview in which both half-joke, half-flirt each other:

Selma: I'm going to sound like a drip, but I really do like to shop. I shop it up. Believe it or not, Karl Lagerfeld took the photos for this piece. He came to my house to shoot me, and my mother couldn't believe it. I told her yesterday that he had come a couple of weeks ago and she said, "You're telling me this now?" He was so dignified. And elegant. I just want him to like me.

Jake: [laughs] I'm sure he does. You know, the nice thing about you is you aim to please--which is why I'm so endeared by you.

Selma: Aww.

Jake: And because you tell me you want to have sex with me all the time. [both laugh]

Jake: Not like that. No, no. You say it in a much more loving way.

Selma: I don't really say it like that!
Source: findarticles.com
Jake between Bridget Monaghan and Selma Blair.

"Before working with Ellen Pompeo in 2002's Moonlight Mile, Jake Gyllenhaal hit on her. "He wasn't Jake Gyllenhaal then," she told Playboy. "I didn't know what else to say, because he'd come over with these compliments and he's much younger than I am. I just said, 'Well maybe we'll work together someday'."
Source: www.people.com
Jake & Ellen at "Moonlight Mile" Benefit Screening, 2004.
Jake & supermodel Daria Werbowy for Vogue, July 2004.