A first date for Valentine’s Day is a patently absurd notion. Why put even more pressure on an already over-hyped holiday fraught with sexual tension? But, as the chosen “group blogger” theme this month, I had to post something.

Sonny's - the scene of my Valentine "dream date" with younger man, James Franco.

So I decided to run with the truly absurd.

I lured Adam into my scheme, and over dinner and a great bottle of wine, we devised “The Perfect Portland Celebrity First Dates” for ourselves. And not just one celebrity date, mind you, but three dates each with three chosen celebrities – one younger, one older – and one of our own generation.

MY DATES

The younger man date
James Franco – to Novare Res Bier Cafe, then Sonny’s
With roles as diverse as Sean Penn’s lover in Milk, the partier in Pineapple Express, and the outdoor adventurer/survivalist in 127 Hours, sexy Franco can’t be pigeon-holed. And, as a PhD candidate, he attends poetry classes at Yale. What’s hotter than that? I’d get him a little tipsy with a few 10% beers at Novare, then spice up the evening with Sonny’s Latin-inspired entrees. We’d keep the night sizzling by sipping pepper-infused tequila at Sonny’s bar.

The man of my generation date
Colin Firth – to Miyake, then Fore Street
This high-brow Brit would want the best, so I’d start at Miyake. Small. Colorful. Fresh. Perfectly packaged. The decor at Food Factory Miyake is itself a metaphor for this tiny Japanese bistro’s delicate delights. Super-fresh and expertly prepared, the sushi offerings would surely impress the Oscar-nominated star, no? Then, off to stellar desserts and cocktails at Fore Street, where we’d sink back in a squishy bar couch and make goo-goo eyes over a slice of Chocolate Souffle Cake.

The older man date
Richard Russo – to Caiola’s
Let’s face it, with nary a hipster in sight and the best comfort food in town, Caiola’s is the kind of cozy neighborhood restaurant where your cheeks turn rosy from wine and animated conversation. What better spot to pick the brain of an older (but cleverly cute) Pulitzer Prize winning novelist? As a Mainer, Russo would appreciate Caiola’s hand-crafted wooden tables and commitment to local, farm-fresh food. We’d stay late sipping coffee and discussing the brilliance of Empire Falls, Nobody’s Fool, and (my favorite Russo) Straight Man.

Adam outside Nosh. Waiting for Brian the animated dog?

ADAM’S DATES

Adam had no trouble picking the younger and older women (lovely Keira Knightly and striking Julianne Moore, respectively), but struggled mightily with the  “same generation” category. He finally chose – after completing the wine AND a couple Gin & Its – “that animated dog Brian from The Family Guy ‘cuz he seems like a great conversationalist.”

Okay. . .

To be fair, we’d discussed my dates first when fully sober, so his choices are a bit sketchy on the details (not to mention – one-third light on humans).

The younger woman date – “I’d take British beauty Keira to Grace, because she does all those period movies and I think the grandness of Grace would impress her.”

The older woman date – “I’d drive Julianne up the coast and woo the ageless redhead at Suzuki.” (Blogger’s note: we just saw The Kids Are Alright and I think the “red thong scene” has stayed with him.)

The same generation date – “Brian and I would grab brews and Pig Belly Apple Pie sandwiches at Nosh Kitchen Bar and discuss the events of the world.”

There you have it.

Blogger’s Note: This post is one of a group of “first-date Valentine” writings being posted today by Portland food bloggers. Visit Portland Food Map for information and links to other posts.