I've felt some serious pain as a sports fan; I grew up a diehard RedSox fan, the son of a diehard RedSox fan. The last 20 years have been great, but the stretch from when I was old enough to care (early 70s) until the breakthrough in 2003 were brutal. Then I became a Nole, and suffered mightily with them for years. My highlowlights....
* The Sox losing the 1986 WS to the mutts, with the ground ball trickling through Buckner's legs (though they'd already blown that game). Felt like I'd just watched my dog get run over by a car.
* Wide Right #1 against um, when FSU was undefeated & top-ranked, led the whole game only to fall behind on a late TD, then march down to get into range for a short, game-winning FG. Sat silenty in the stands, with 70,000+ other stunned FSU fans, for about 45 minutes before mustering the strength to shuffle down the stairs & back to the car. I felt sick for a full week after that game.
There were several others, mostly FSU losses to um.