Age Inappropriate

For older men who’d like to romance a younger gal, there’s no better cinematic inspiration than the films of Woody Allen. Allen has doggedly pursued this theme for the better part of the last 20 years. Like Hugh Hefner, Allen’s leading ladies keep getting younger as he gets older. How does he do it? As a tribute to his latest film, Whatever Works, we present 10 tips from Allen’s movies for snagging a younger woman.

By Graham Flashner

Tip # 1 – Hang out at a Manhattan prep school

Age Difference – 25 years
Manhattan (1978)

It began here, with Allen playing a 42-year-old TV writer involved with Mariel Hemingway, an impossibly sweet and innocent 17-year-old Dalton student. “I’m dating a girl who does homework,” Allen jokes, but the real question here should be: where are her parents?

Tip # 2 – Chicks dig the Svengali figure

Age Difference – Combined? More than 30 years
Hannah and Her Sisters (1986)

Barbara Hershey, as Hannah’s beautiful younger sister, is the object of affection of not one, but two older suitors: Max von Sydow, the tormented Soho artist that she lives with, and Michael Caine, who’s married to Hannah but lusts after Hershey. The oldsters strike out here, though, as Hershey winds up with neither.

Tip # 3 – Be her Daddy fixation

Age Difference – More than 30 years
Husbands and Wives (1992)

Allen, as a creative writing prof at Columbia, is pursued by Rain (Juliette Lewis), a brainy student who’s got a weakness for father figures. Allen takes the moral high road here and puts the brakes on before things get out of hand. Alas, shortly after the film’s release, Woody and Mia Farrow’s marriage dissolved after it was revealed that Woody was dating Soon-Yi Previn, her adopted daughter.

Tip # 4 – Have a mid-life crisis

Age Difference – More than 25 years
Husbands and Wives (1992)

Allen's sidekick in the film, played by the late director Sydney Pollack, leaves his long-term marriage and takes up with a 20-something aerobics teacher. “I want a girl who digs her nails into my back and screams when I f*** her” Pollack says. Of course, that can only last for so long, and he eventually slinks back to his wife.

Tip # 5 – Be her rescue fantasy

Age Difference – More than 35 years
Mighty Aphrodite (1995)

Allen goes in search of his adopted son's real mother, who turns out to be a beautiful young prostitute (Mira Sorvino) who becomes infatuated with him. Though Allen the character nobly resists Sorvino’s sexual temptations, you can almost feel Allen the filmmaker wishing he could consummate the deal. We kind of wished that at age 60, he would find women his own age.

Tip # 6 – Read her like a book

Age Difference – More than 25 years
Everyone Says I Love You (1996)

In what alternate universe would Julia Roberts find Woody Allen seductive enough to describe him as “sexy” and “magical”? Well, this is a musical fantasy, after all. Allen exploits it to the hilt, leading Roberts to believe she’s met her soul mate. If you find that unbelievable, wait’ll you hear them sing.

Tip # 7– Don’t be too much older

Age Difference – 30 years
Deconstructing Harry (1997)

This was Allen’s poison-pen response to the public disgust over the Soon-Yi revelations. His biting humor and lecherous obsessions are on full display here in his role as hounded writer Harry Block. The obligatory young girlfriend here is Elisabeth Shue, a mere 28 years younger than Allen in real life.

Tip # 8 – Be a once-famous film director

Age Difference – More than 35 years
Hollywood Ending (2002)

As washed-up, suddenly blind director Val Waxman, he somehow still gets a hot young actress girlfriend (Debra Messing). And he gets hit on by an actress in his film, who earnestly tells him “If I trust a director to direct me – I trust him to make love to me.” With Allen looking a bit long in the tooth at age 67, that’s a scenario best not considered.

Tip # 9 - Look and sound like Javier Bardem

Age Difference – More than 20 years
Vicky Cristina Barcelona (2008)

In one of the smoothest pick-up scenes on film, painter Juan Antonio (Javier Bardem) invites two young American girls he’s just met, Vicky (Scarlett Johansson) and Cristina (Rebecca Hall) to come away with him for a weekend in Barcelona. “We'll eat well. We'll drink good wine. We'll make love,” Juan purrs. Says Vicky: “Who exactly is going to make love? Responds Juan: “Hopefully, the three of us.”

Tip # 10 – Find someone dumber than you

Age Difference – 40 years
Whatever Works (2009)

Allen cast Larry David in his place, letting the cranky “Curb Your Enthusiasm” star score with the young babe instead. Demoralized physicist David tries to find meaning with a dim-witted Southern pageant queen (Evan Rachel Wood). Why would a nubile 21 year-old be attracted to a 61 year-old curmudgeon? You’ll have to see the film to find out. And hope that Woody Allen won’t be chasing 18 year-olds when he’s 80.