I'm not going to lie to you. My fanaticism for Will Sheff (lead singer of Okkervil River and member of Shearwater) is borderline obsessive. As one of the best living songwriters of our generation—yeah, you heard me—Sheff's talent for writing music that is both beautiful and intelligent ranks him alongside the likes of the best (if not just the most under-appreciated) songwriters of this era, Joe Pernice (of the Pernice Brothers) and John Darnielle (of the Mountain Goats). There, I said it.

While Sheff represents the new era of dreamy indie frontman—think bookish, confident, and a man who looks good in glasses—he has a darker side, which makes him more of a performer and less of a misplaced-librarian-with-vocal-mic presence onstage. Okkervil River's latest, Black Sheep Boy (and the EP sequel, Black Sheep Boy Appendix), is loosely written around the life of obscure '60s folksinger Tim Hardin (a career and tragedy reminiscent of Tim Buckley, but without the famous, and equally tragic, offspring). The Black Sheep records act less as a open-ended tribute to an artist that only vinyl collectors know, rather they sound sharp and modern, as Sheff's voice cracks and struggles through small bouts of emotional flare-ups, only to settle back into his confident croon all within the span of a few minutes. And somewhere between the tipping of the cap to Tim Hardin and the polite loosening of the tie, you find yourself falling for Sheff. He's the everyman—the accidental lead singer—who might as well be a professor, construction worker, or you, or me.

Come this Valentine's Day, when Sheff plays a rare solo show here in Portland, it's going to be an awkward situation when I interrupt the show to present him with flowers and candy. It'll be awkward for him, seeing as I'll probably ruin the show as I present him with these gifts of my affection from the crowd. It'll be awkward for my girlfriend, as if dating me wasn't enough of a burden, as I ruin another Valentine's Day. And, most of all, awkward for me, because I'm not sure if roses and chocolates are really his thing. What if he's allergic or something? Should I just have gotten him a stuffed animal instead? Really, really, awkward...

Will Sheff performs at the Towne Lounge on Tues Feb 14