The Situation: It’s date #4 with Mr.Improv, the cute, Andy Samberg-esque friend-of-friend-of-friend who you’ve recently added to your fall ’07 dating line-up. Dates 1 thru 3 had run the gamut from fun (taking in an Upright Citizen’s Brigade performance) to crazy (break dancing a la Rock Steady Crew circa ’81 at 4 a.m. at the SNL-after party) and were always, predictably enough, laughter-filled. He’d always been in high spirits, full of self-deprecating stories about the sitcom pitching process, and he’d always seemed to be “in talks with” the Farrelly brothers about “something big.” You weren’t totally sure about or impressed by this, but you turned the B.S. alarm off because he was 1) cute 2) funny 3) his smooth moon walking moves were mirrored elsewhere.

But now, with the writer’s strike showing no signs of letting up, his jobs (and paychecks) temporarily cancelled, and him having to temp at a law firm (“Where brain-cells go to die,” he said of his fluorescent-lit cubicle) you’re afraid that light-hearted act you’d been enjoying might now be at intermission. Dealing with a depressed jokester is not something you’re familiar with. (Him) hoping to drown all sorrows and (you) potentially ignite some flames, you two are hitting up the local dive bar to imbibe a few beers–preferably cheap $2 PBRs.

Gawker’s Free Paris tee

The Solution: Avoid the temptation to be witty/try to cheer him up by wearing an ironic t-shirt, even the feisty slogan tees which are now so passé that they’re almost in again. Chances are that they’ll just remind him of all the funny stuff he isn’t writing. Cozy and cuddly is the name of the game for you.

Go for an Ali McGraw in Love Story look because nothing 1) spells hard-to-resist preppy sex appeal 2) suggests fall romance and 3) says Tragedy? Who cares!?! Let’s just live in the moment! more than her iconic wardrobe. Plus her whole “Love means never having to say you’re sorry” look will show you care, without having to dwell on his bad luck. Likewise, a heart necklace shows that you’ve got a sensitive side too. Knit accessories are key and a cashmere sweater will turn you into the soft shoulder he can cry on—and if he gets over his woes early enough in the evening—and maybe more.

Burberry Sweater, Urban Outfitters beret, J.Crew Cashmere T-neck, Paul Smith Scarf, Hollywould boots, Urban Outfitters heart necklace, Stella Jeans.

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