My own first response to Sean Parker's 9,500-word defense of his wedding, posted Thursday on TechCrunch, was a practical one: "Did he spend his entire honeymoon typing away at this?" (Sure, a chain-of-thought-style post like Parker's might come together relatively quickly, but a feature article of half that length that might run in Inc. can take 80 hours to write and rewrite, per the self-assessment of one of my colleagues.)

But the length of Parker's cri de coeur is a relatively minor problem. A much larger one is the tone, which manages to be both aloof and defensive. That robs the piece of its ability to accomplish what it seems to be attempting. It's pretty hard to elicit sympathy without a dose of humility.

To be fair, Parker, who's an investor, the founder of Napster, and such a Silicon Valley mainstay he appears from time to time in celebrity magazines, was put in a rough place. His decisions surrounding his $4.5 million wedding were bashed far and wide online, by both media outlets and casual observers--some of the latter of whom issued threats to him on Facebook. He wasn't given an opportunity to react in many of the regurgitative blog posts.

So Parker punched back. And he missed the mark wildly. We decided to embark on our own little game of fantasy and consider how this mess might have gone differently. I called some of New York's top public-relations pros, and asked how Parker should have handled the controversy. They proposed three different strategies--each of which could have been useful here.

1. Try a little tenderness.

"He hasn't yet realized that he's reinforced a negative stereotype with this long rant. He showed no awareness of an excessive display of wealth; no acknowledgment of another worldview outside his own. This could be a worst-case study from Harvard Business School.

"You need to admit fault if fault exists, and try to understand the other person's point of view. In this situation, even if you don't agree, you need to show empathy to what's obviously been a groundswell of opposition. If you can see someone else's point, you're going to win in the court of public opinion. Parker could show some vulnerability. That could go a long way at tamping down the hostility."
-- Steve Cody, managing partner and co-founder of Peppercomm

2. Plan ahead. (And grow up!)

"The part that stood out to me most was when he said 'The biggest mistake we made in wedding planning was forgetting about the media.'

"Most public figures anticipate a reaction. And if it's a negative reaction, they either choose to ignore it or release some sort of statement addressing the issues, which I think would have been appropriate here. But this wasn't a statement. It almost seemed like he found out a group of his friends were talking about him behind his back and he was writing an email to them about how hurtful it was."
-- Devon Giddon, director of communications at Thrillist Media

3. Just shut up already.

"Sean Parker got a huge backlash for all the things he did in this forest with his wedding. But it seemed to have resolved itself a week later when it came out that the forest wasn't as destructed as we'd thought. I thought the air was cleared.

"Doing this was like waving a red flag in front of 100 bulls. One of the things people need to know is when to shut up. Don't bring it up again! I don't understand what prompted this. Maybe being a wealthy and powerful guy he still had issues to get off his chest. I'm mystified as to why he dug up a dead horse. You have to know when you've said what you've said and leave well enough alone. This doesn't change anything."
-- Drew Kerr, president of Four Corners Communications