I am not familiar with the idea of a cigar of shame.
You’re obviously too young to remember the Clinton Presidency.

Have you ever dated someone really rich? What’s it like? And don’t get cute with me talking about metaphorical wealth I mean $$$$$$
You realize that when you date someone wealthy, it doesn’t suddenly become your money, right?

How do I get and keep a rich boyfriend?
You’re not hot enough.

I’m having trouble distinguishing the difference between one bad instance and a mark of true character. How do you tell?
Motive.

A guy I just started dating and I had sex for the first time in the middle of the day and he was going down on me while Sam Smith was on and it was the best orgasm ever. Now I can’t stop listening to Sam Smith.
Nice. That’s how I became a fan of alt-J.

Why is everybody like “Robin Williams” and nobody like “Lauren Bacall”? It’s Lauren Bacall, for Christ’s sake!
Lauren Bacall is a legend and a badass, but she hasn’t been culturally relevant for half a century. Plus, she died during the refractory period of our collective grief-gasm for Robin Williams. We didn’t have another one in us quite yet.

Thoughts on D/s relationships? Have you ever been in one, and do you have any advice for someone who’s considering it? I’d appreciate it.
I’ve been in several. It’s not really my thing anymore, nor is it the kind of subject where generic advice is particularly useful, and since I don’t know anything about you, the best I can do is point you to a book called SM 101 and either the Bottoming Book or the Topping Book (or both).

If it is all about oil then would we as a nation be smart to do what Germany is doing and move quickly to 100% renewable energy? Or we might keep our ban on exporting oil and use all the oil we just found in Utah to stay caked in the stuff till we no longer need it. Thoughts?
If we were smart, we wouldn’t just make it about us. We’d spearhead a multinational push for renewable energy. I talk about that more in depth in my post “On Our Ecosystem.”