By hard, I don't mean tough in the traditional sense.
I want to what the most difficult/painful/agonizing/etc... thing you have ever had to do is?
I will be reporting back with mine in the next 24 hours.
Tomorrow/today will suck.

once i benched 275lbs.

i don't recommend it.

switched my eyeballs so they were in the wrong sockets

skinned a horse at full gallop.

Four years ago, when I broke up with my girlfriend of nearly eight years. I loved her, but knew I had to leave. It was the right decision, but I felt selfish and evil doing it. And the breakup was protracted over months, as can be expected. Fucking gutwrenching. There can be nothing worse than hurting someone you love and who loves you. Amazingly, we are very good friends now, for which I'm lucky and most thankful.

Moving to GA before my senior year of high school and having a crisis of identity in the middle of a big city. I can barely remember those two years there but goddamn...when I do, I have only terrible memories that embarrass the fucking hell out of me.

That and burying a close friend are the two hardest things I've ever had to do.

Leaving my ex-wife. All my fault. I still feel guilt about it 15 years later.

Telling my father I was kicked out of graduate school.

Jon

divorce is awful.

divorce from a vindictive drug addict, perhaps slightly more so.

Delivering a beatdown to otherwise strong contenders, my miscarriage/failed pregnancy in the (early) second trimester two years ago is the G.D. worst, hands down.