This isn't pickup meeting girls stuff as such, but I read this recently.
I really enjoyed his earlier book - Black Swan - which is all about calamitous events you can't predict that are game changers.

In Antifragile he puts forward an interesting idea...
Fragile stuff/businesses/people get hurt by randomness
Robust handle randomness
Antifragile benefit from randomness.

Everyone faces difficult circumstances but it's interesting to think how you can move to having an almost stoic like view where you almost crave randomness/calamity because you know you will benefit from it.

If you enjoyed Black Swan or are intrigued by the idea I would recommend.

Cool recommendation, thanks.

I thought it was interesting in theory, but struggled how to use it to change/add something new to my life?

Fair point. How I see it is ideally you are present not thinking constantly and unfazed by anything- which is unrealistic unless you are Dalai Lama.
In bad times most people think about stuff constantly and make it worse.
If you can't turn off your thoughts it's helpful if they can at least become positive, especially if you start believing you are actually benefiting from the tough situation.
I already had some ideas around this and the book helped me crystallise my thoughts.
How you take it forward/benefits
1 Helps rewire your thinking about what constitutes 'bad times' which will make them more palatable - I think this is the money
2 Gets you thinking about seeking out uncertainty to get out of your comfort zone.
I think maybe that's more what I mean as opposed to 'bad times' but it'sall perception relative - I'm not talking about extreme hardship or physical injury, but eg. a trip into the jungle might be hell on Earth for some folk but already a good holiday for you so that wouldn't be hugely out of your comfort zone anyway.
Not sure if that answers or makes it more confusing!