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About Chicago

Anyway, we meet up, me and this girl, and I’m nervous as hell—like, “Am I gonna screw this up?” I’m overthinkin’ it, naturally, ‘cause that’s my thing. She’s gorgeous, smells like lilacs or some crap, and I’m sittin’ there goin’, “Larry, don’t be the pale man, don’t freak her out!” We’re drinkin’ wine, talkin’ dirty, and it’s goin’ great—till she says, “I’m into roleplay.” ROLEPLAY? I’m like, “What, like *Pan’s Labyrinth*? You want me to be the faun?!” She laughs, thank God, and I’m saved. Turns out she meant somethin’ kinkier, which—whoa—surprised the hell outta me. Happy? Oh, I was thrilled, like a kid with a golden ticket!

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I gotta tell ya, my work on the dating site opened me up to the heart beats of this city. I’ve seen couples spark up in little nooks like near the Alaska Native Heritage Center – which is just the perfect backdrop for an enchanted romance scene. I’ve seen tears, laughter, and even the occasional epic breakup. And sometimes I laugh, kinda like Fran in The Nanny, “Oh, helloooo, darling!” with that nasally giggle that just makes the whole day brighter.

Letter: Mayday