From my perspective, if you are in a place of prestige and you want to avoid damage to your image, hiding your quirks is maximizes the chance that they will be discovered in a way that precludes you controlling the how it is released. If image malpractice is the issue, keeping this in the open is an inoculation against more damaging future revelation. The trade-off is that you may lose credibility up front. Given EY's eschewing of the "normal" routes to academic success, and the profound strangeness that a some of the ideas we take for granted have at first blush to anyone who hasn't read the sequences, I don't thing OK cupid is doing much damage.
Finally, I noticed when I first read this that the article gave me the squicks. In trying to compare the feeling to a known quantity, I realized it was analogous to when my religious parents would scandalously tell me of a couple who are "shacking up". The feeling of someone sharing psudo-private information in a way that does not explicitly make a value judgement, certainly does implicitly. I rather doubt that was your intention, however, you might want to be aware of the reaction, if it was not intended.
tl,dr; EY's just this guy, you know?
The rationalist in question, of course, is our very own EY.
Quotes giving a reasonable sample of the spectrum of reactions:
Why is this important to consider?
LessWrong as a community is dedicated to trying to "raise the sanity waterline," and its most respected members in particular put a lot of resources into outreach, via CFAR, HPMoR, and maintaining this site. But a big factor in how people perceive our brand of rationality is about image. If we're serious about raising the sanity waterline, that means image management - or at least avoiding active image malpractice - is something we should enthusiastically embrace as a way to achieve our goals. [1]
This is also a valuable exercise in considering the outside view. Marginal Revolution is already a fairly WEIRD site, focused on abstract economic issues. If any major blog is likely to be sympathetic to our cultural quirks, this would be it. Yet a plurality of commenters reacted negatively.
To the extent that we didn't notice anything strange about LW's figurehead having this OKCupid profile, LW either failed at calibrating mainstream reaction, or failed at consequentialism and realizing the drag this would have on our other recruitment efforts. In our last discussion, there were only a few commenters raising concerns, and the consensus of the thread was that it was harmless and had no PR consequences worth noting.
As one commenter cogently put it,
I'd argue the same reasoning applies to the community at large, not just EY specifically.
[1] From Anna's excellent article: 5. I consciously attempt to welcome bad news, or at least not push it away. (Recent example from Eliezer: At a brainstorming session for future Singularity Summits, one issue raised was that we hadn't really been asking for money at previous ones. My brain was offering resistance, so I applied the "bad news is good news" pattern to rephrase this as, "This point doesn't change the fixed amount of money we raised in past years, so it is good news because it implies that we can fix the strategy and do better next year.")