Derek Webb Wore a Dress to the Dove Awards and is Deeply Committed to Telling You About It

Note: I wrote this for my WORLD Media column space…only to find out that somebody else had beat me to the punch. Oh well. Now I can use it here.
I didn’t really know who Derek Webb was, which is no big deal because I don’t know who a lot of people are. When I grew up, the kind of tacit understanding was that you wouldn’t know (much less care about) most people. Webb, apparently, was a part of a band called Caedmon’s Call in the 1990s, and I say “apparently” not to be dismissive or a jerk, but only to indicate that I wasn’t real familiar with this (see above).
But a lot of people were, and a lot of people deeply resonated with his later, reformedish, theologically-solid songwriting, which songwriting took place before the now-almost-cliché and very public deconstruction/apostasy experience that usually starts with “I have some questions” and usually ends with worshipping the idea of uncertainty while also for sure looking like Michael Stipe from REM.
I don’t pretend to know what “happened” to Derek Webb, and I actually won’t really pretend to care all that much, inasmuch as I’m not capable of caring about everything, and every person, all the time. And neither is he (Webb, not God). However, with the performative deconstruction deals I always get a.) very sad, because if you think about it it’s the saddest thing imaginable, and then b.) very annoyed when said celebrity uses their charisma, platform, or whatever, to lead little ones astray.
Also, the performative deconstruction deals are almost always accompanied by an obsessive/compulsive level of still posting and writing all the time about the thing that was deconstructed or walked-away-from, sort of in the fashion of a guy who insists that he’s “totally over” the breakup he endured a year ago but can never stop talking about the girl.
About the dress. I had a couple of friends send me the video Webb posted which was his “thesis statement” on why he wore a very 90s-ish, ironic-little-old-lady dress to the Dove Awards, which (the awards) is another thing I don’t care about. But anyway, Webb was super self-satisfied about what an amazing ally he was to all sorts of marginalized people, while definitely keeping the focus on himself (a cis, married ((to a woman)) white male) through posting several days’ worth of dress-related photos/statements/theses about what a good ally he is. My immediate thought was something along the lines of, “Wouldn’t a really good ally post about the marginalized people he’s trying to help platform?”
A word on the dress itself: really pretty modest (the opposite of a plunging neckline) and very 90s art-girl. The shoes he wore (patent leather Mary Janes) were legitimately worn by my wife in the 90s in very cute ways. My second-most-immediate thought was, “My wife would love that outfit.” My third-most-immediate response was, “Where does a middle-aged man purchase an ironic dress? Forever 51?” What a strange world we live in.
A word on men wearing dresses for PR-or-shock-value: my favorite example of this was Saints running back Ricky Williams who posed on the cover of ESPN the Magazine with his coach, Mike Ditka, while wearing a wedding gown. But this wasn’t a social statement as much as it was a humor thing.
A word on the friends with whom I interfaced about this: one group was comprised of people who wanted to make fun of it (which I was all too eager to participate in), but another group, the group that legitimately loved his actually-Christian music, was legitimately sad. And I became legitimately sad for/with them, which ended up being a way stronger emotion than the making-fun (which was fun, but only sort-of).
I’m wasn’t especially moved or angered by the dress-wearing. I ended up just feeling glum, and not just about the surrealist-hellscape we’re living in, but for Webb himself, who I’m sure would dismiss my glumness on his behalf as just more hatefulness from a hateful guy who represents hateful things (the church, doctrinal distinctives, etc.). But I really do want good things for him – the best of which would be a scenario in which he sprints to the foot of the cross, which is exactly what I did when the Holy Spirit pursued me out of the hellbound race I was running. This was the moment my life actually started.
The Lord could do this, immediately, for Webb, and I hope that He does, because this would bring maximum joy that would far outstrip the momentary thrill of a few “good-job-Derek’s!” from an impossible-to-please audience.
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