A Date with Jake Gyllenhaal: A Possible Dream?

The last time summer Chilmarker and movie star Jake Gyllenhaal, agreed to be an object of desire at the Possible Dreams Auction on Martha’s Vineyard, in August of 2008, someone with a bursting wallet paid $8,500 to visit Gyllenhaal on the set of “the untitled moon movie.” It’s still untitled and, guess what? It was never made! So hopefully the top bidder won an alternate filmmaking experience—maybe spending face time with Jake on the set of “Source Code”? Wow. I would have shelled out $8,500 for that. Of course, my check would have bounced.

This was big bucks going to a noble cause, Martha’s Vineyard Community Services, but an on-set visit had to be Gyllenhaal’s easiest gig ever. A production assistant would have cleared the Possible Dreams party with the guards at the gate. Between takes, the star with the dreamy blue eyes assuredly came over, shook hands, and even conversed for a while.

Why would he do that?

Because he’s a cool guy! I’ve never met him, but all the facts line up: First and foremost, he looks angelic. I know this isn’t the top criterion for most women, but for über-moms like myself, you just want to clamp a hand around his chin and exclaim, “What a puss!” (He must love that!)

He was born in December of 1980, so he turns 31 at the end of the year. (I figured that out with astonishing ease, without even resorting to a calculator.) His sister is the actress Maggie Gyllenhaal, his dad the director Stephen Gyllenhaal, and his mom screenwriter Naomi Foner. His parents divorced several years ago, but they were tight for 30 years, enough time to give their kids what they used to call healthy formative years.

Stephen was descended from an aristocratic Swedish family; I’m thinking the double A’s are kind of classy. Naomi is Jewish, and Jake, in lieu of a formal bar mitzvah, volunteered at a homeless shelter to celebrate the event! This was meant to give the young man appreciation for his privileged background.

He is now, like most good Jewish boys, a Buddhist, having received his earliest teachings from family friend, Robert Thurman (Uma’s dad!), a Columbia professor and household name in the world of Indo-Tibetan philosophy. But it wasn’t all intellectual. Another family friend, Paul Newman, taught Jake how to drive. Fast. And Jake’s godmother is Jamie Lee Curtis, for crying out loud. And are you ready for another Gyllenhaal family factoid? Maggie married actor Peter Sarsgaard. What are the odds of finding a marriageable man with double A’s in his surname? There has to be some cosmic significance in that, but I can’t for the life of me figure out what it is.

Gyllenhaal sounds like he’s always been a bunch of fun. In his teens he had a Vineyard summer job as a lifeguard. He says he sometimes grabbed a life buoy and charged over the sands, Baywatch-style, to pretend something exciting was happening. One time a swimmer got lashed by a jellyfish, and Gyllenhaal peed on the welt to remove the sting. That’s fun, right?

He’s had some famous GFs—as why would he not? For instance, Kirsten Dunst and Reece Witherspoon; the latter visited him and his family on island with her two tots. She recently married, so we can assume she and Gyllenhaal are no longer dating

Like most kids growing up in LA, who also happen to have parents in The Biz, Jake was offered roles at an early age, although he had to get the scripts vetted by his folks. (They turned down a part for him in Mighty Ducks). At 11 he played Billy Crystal’s son in City Slickers. But the role that transformed him from young working actor into heartthrob of the first order was his dazzling performance as a gay, or gay-ish, cowboy in “Brokeback Mountain,” co-starring his late buddy, Heath Ledger. This cinematic same-sex romance didn’t stop girls from throwing themselves at him: His biggest fans call themselves “Gyllenhaalics”.

So, regarding Gyllenhaalics, some of whom summer here, with fathers who’ve given them ponies, brand-name boarding schools, and convertible McLarens, how about asking Daddy to shoot the wad at the Possible Dreams auction on a dinner with Gyllenhaal; at L’Etoile in Edgartown? Or a moonlight cruise on Mad Max? Or, Gyllenhaal being an environmentalist, maybe a beach litter clean-up; what better way for two young people to get to know one another?

Not that anything romantic would be expected from the blue-eyed star; that’s asking too much for a four or five-figure auction bid.

For any Gyllenhaalic who wants to cut to the literal chase, Gyllenhaal likes to run in the Chilmark Road Race. In 2009 he came in 52nd. He may not be Olympics material, but yearly up to 1,500 people participate in the dash down Middle Road, so he might be hard to catch. This summer’s competition is set for August 13, so that gives Gyllenhaalics plenty of time to train.