Pretty much all my fatty moments have involved smoking copious amounts of ganja...
One night my wife was at work, so I ordered an extra large pizza. This is NY-style pizza, so the thing was about the size of a manhole cover. Figured I'd eat some, save the rest for breakfast/lunch the next day. Ate two pieces. Still hungry. Ate two more pieces. Still hungry. Now there's half a pizza left and I've reached a critical point. If I eat one more piece, my wife is going to come home and be like, "What the hell did you do?" So I ate the whole fucking thing, then walked down the block and threw the empty pizza box in my neighbor's garbage so the wife wouldn't find it. Still not sure how I didn't vomit that night.
Back when I lived in Portland I would go to Blazers games all the time and they give out coupons to all fans for a free Taco Bell chalupa if the Blazers score more than 100 points. Got super baked one night and had a hankering for some chalupas, then I read the fine print and the coupons say, "Limit 1 chalupa per person, per visit." So I do a quick Google Maps search for all the Taco Bells in Portland, then spend the next hour driving all over town cashing in coupons. Got home and ate like seven chalupas. I honestly thought I was going to die.
Going in the way-way-back machine, I got drunk in college one night and was like, "Hot dog eating competitions are for pussies. That doesn't look so hard." Decided to cook and eat an entire 8-pack of Ballpark franks, with buns and all. I barfed so fucking hard that I thought my intestines were going to come out my mouth. Not a real proud moment in my life.