The first time a WW reader told me to "fuck off," it was in response to a comment I made about the Aladdin Theater's typical audience. In a fairly positive preview of OPB's live radio variety show, Live Wire!, I had written that folk singer Robbie Fulks (one of the show's guests that month) was "sure to please the seated, semi-square folksters who frequent the Aladdin." Guess the truth hurt. On a recent visit to that very venue, however, I found myself in that angry reader's shoes.

I took my father—who was visiting from Illinois—to see singer-songwriter Mason Jennings last week. I found myself sitting in the balcony for the whole show—and I even developed a somewhat crotchety attitude. Jennings opened with two acoustic numbers, including an excellent rendition of "Bullet," which inspired half the crowd to rush the stage; I assumed we were in for a poignant solo set much like Jennings' 2006 Aladdin appearance. But then he brought out a band. And though his bassist and drummer were enthusiastic, skilled performers, I was actually a bit put off by how much they were rocking.

But Jennings appeared to be having a blast, and he was giving his audience—mostly hippie- or frat-leaning twentysomethings—exactly what it wanted. What I wanted, and what I wanted my dad to hear, was the "deeply personal, sappy crooner" I had described in my preview of the show (which I read to him beforehand over dinner at Pizza Oasis). But even during relatively brash, upbeat songs like "Godless," my 63-year-old father seemed to be thoroughly enjoying himself. He mentioned before the show that he'd never seen a bass guitar (really!), and—after Jennings and band played a moving version of "Be Here Now"—he asked, impressed, "Does he write his own songs?"

This isn't to say Jennings and company weren't fantastic: They played with fervor for nearly two hours. And Jennings did alternate between playing with his band and delivering tearjerkers such as "If You Ain't Got Love" and "If You Need a Reason" on his own. He even played a gentle cover of Buddy Holly's "Every Day" (my dad asked if it was an Everly Brothers song) and an affecting "Jesus Are You Real" encore (which reminded my father of R.E.M.'s "Losing My Religion").

Over the course of the night, my dad compared the life of a touring musician to that of a professional athlete, he asked me if you have to "rock" to be popular, and he said it was "really neat" to see a band play live. On the way back to the car, he admitted that Jennings' mellow songs were more his speed, and I joked about bringing him into my "rock-'n'-roll lifestyle." But, eating my Live Wire! words, I realized that Jennings' softer tunes were also more my speed—that, sometimes, I'm "semi-square," too.

Here Comes Your Fan is a weekly column featuring pontifications on all things music-related from WW's trusty music editor.