My mother is well-intentioned but fairly clueless. Now in her early 50’s (twenty years older than I), she makes, and has always made, regular attempts to “connect” with me on what she thinks is appropriate for my generation and worldview. Unfortunately, more often than not, she just comes off as, well, kinda dorky. I can’t decide whether her positive intent in trying to relate to her kid overshadows the embarrassment I feel for the resulting inadvertent foolishness. Of course, I just play along; it would be mean to call her out on her dorkiness. Besides it usually provides a funny story for later, so I really can’t complain. 
Case in point: Years ago, when I was in high school, she met at some school event a classmate I had befriended. He was rather flamboyantly out of the closet, a rather brave stance for a freshman at a conservative rural school. “I think it’s neat that you’re friends with him,” said my mom later. That impressed me. But she continued: “I like going to <a dive nightclub in town>, because we get to watch the gay guys kissing in the corner booths.” I honestly don’t remember how I responded, because I was too busy repressing what I wanted to say, which was: “HNGWUH?”
A few years later, after graduating and leaving for an out-of-town college, I brought my girlfriend home for a weekend visit during my freshman year. We didn’t flaunt the fact that we were sexually active, but we weren’t circumspect either: She stayed in my room, we showered together, and so on. At one point during the weekend, my mom got a moment alone with me. “She’s very cute,” she said, which naturally I agreed with. “Listen,” she continued. “If you ever need any, y’know, sexual advice, you can always ask–” her husband of a few years, my stepfather, a definite improvement over my biological father. And her eyes lit with a disturbing light: “He’s very good.” Again, I don’t remember exactly how I responded, because I was trying really hard not to say what I was actually thinking: “AAUUUEEEWWWGGHHH. Jesus, Mom, don’t invite me to imagine you getting nailed. Goddamn.”
Recently, she’s started to going to bars and nightclubs to hear blues bands performing live. (This isn’t as funny or weird as the above. It’s what got me thinking about the subject, though.) I’d applaud that, but given my mother’s notorious lack of taste (she wanted to serve cocktail weenies on toothpicks at my wedding, for example), I wasn’t sure what to expect. Turns out I was right to question it. As she invited me and my wife to come along, and talked about how much she was enjoying her newfound fascination, I asked if she was a fan of Robert Cray. Nice, safe choice, I thought, prominent and mainstream and, as a bonus, from Seattle, for a local connection. Nope: She wrinkled her nose. “He’s too, uh, extreme for us,” she said. I got to hear a CD she had picked up at a show; this stuff just barely qualifies as the blues. It’s more like country-and-western with heavy drums, slightly edgier guitar work, and raspy-voiced singers. But no, she thinks it’s “dirty bar blues.”
Yeah, yeah, I know, it’s the job of parents to embarrass their kids, and there will always be a generational chasm. My question, though, is, why don’t parents realize this? Do you guys have similar stories? How do you cope?
