I asked her out, hoping she’d say no.

I asked her out, hoping she’d say no. Well, not hoping beforehand, but I was happier after her rejection than I would have been otherwise.

We were in the grocery store. She inspected a can of Campbell’s soup. She replaced the can it back and grabbed another. I asked, “Good read?”

“Not really,” she said.

I asked what she was looking for.

“Sugar,” she said. “It’s in everything.”

“Why?”

“I gave it up for Lent.”

“Do you always give something up for lent?”

“Yeah, it’s like a second shot at a New Year’s Resolution.”

I asked if she’d enjoy grabbing coffee. She said she has a boyfriend, “but it’s still nice to talk in the grocery store.”

Walking away, I celebrated. I hadn’t asked her out because I wanted to go on a date with her. I had asked her out because I decided to start dating again. Asking someone out is uncomfortable, so you’ve gotta hurdle it at your first opportunity.

Suffering as a self-improvement strategy?

Making the self suffer is a cornerstone of many successful philosophies:

I was prompted to consider this strategy by Conan O’Brien on his podcast with Stephen Colbert. Both Catholics, they described intentionally putting themselves through strife. “I did hairshirt behavior,” Colbert says (34:37).

Conan (36:27): “This is pain… where any normal person would tell you, any therapist would say, ‘This suffering is unnecessary. You achieved nothing with this suffering.”… I put myself through a lot of torture. And here’s the crazy thing: what happens when you do that and then magical things start to happen for you? You can’t see me because it’s a podcast, but Stephen just pointed his finger at me as if to say, ‘You nailed it.’”

Stephen, a few lines later: “It works.”

Conan: “What I hate, I hate… I hate thait it fucking works.”

Stephen: “And the magical thinking magically thinks that magical thinking worked.”

Conan: “It’s the biggest fight I’ve had over the last five years with therapists and friends.” … “Therapists have said, ‘You don’t need the suffering.’ and I 80% believe them and I’m 20% like, ‘what the fuck do you know?'”

Is making yourself suffer a strategy for improving? Does it work? Comments greatly appreciated.