How to drop a bomb on a group conversation

(2017)

Last night I was having dinner with three women who I've known for a very long time. I dated one many years ago, and we've stayed friends since. Today, one is still single and basically a spinster, one is divorced, and one is married (this sounds like the setup to a sitcom, I know).

So we're chatting, and I tell them that as usual I'm not seeing anyone seriously, and they want to know why not. They're pretty familiar with my ways but for some reason the spinster and divorced ones want to know when I'm going to "settle down." I tell them about Mating in Captivity and  then about how I'm seeing Bike Girl... they comment about how young she is (she's not) and I say it:

"I don't really like dating women over 30."

To be sure, I said it with a cheeky grin and a bashful, "What can you do?" posture. The reaction was amazing. What is wrong with me? Am I immature? Do I have a complex from childhood? Do I not understand what older women have to offer? There were many others in this vein.

One of my friends even said I was disgusting!

I agreed and told her that she loves me because I'm disgusting and willing to tell the truth when most people lie.

This is the sort of thing that should only be said if you're willing to play the pariah for a while. I was happy to and I knew them all well. This is NOT the sort of thing I'd usually say, especially to people I don't know well, though I have sometimes used the "I don't really date women over 30, but there's something different about you" line on women over 30 I want to sleep with (or have been sleeping with, or am ramping up to sleeping with).

It's a high-variance line that tends to create anger and fire. Be careful using it… only do it if you're willing to create a lot of anger (but also sometimes comedy, if it's done well). Impolite truths make people angry.

In some sense saying this kind of thing is socially stupid. But I did it anyway because I thought it was funny. I also don't mind being ganged up on; it usually makes me laugh. If you’re having fun, there’s a decent chance the people you’re with are having fun too.

Plus, wine. Blame it on the alcohol. Time-honored strategy. Almost all human cultures make use of alcohol and other intoxicating substances, maybe in part so that people can say the things that are true but also socially unacceptable.