Losing a good job can be rough .

Having your hydroponic connection move away.

My condolences, I can not imagine your heartache.

Charlie Brown and its holiday specials not airing on television this year because Apple TV+ earned the rights in a new partnership.

Not close to death or sickness or cheating, but Pinchin' one of your "boys" on the toilet seat aint no fun.

Is this an old thing I am not aware of?

Getting married
Having children
Having children who are involved in sports
McRib going away

A big fish straightening a hook.

Get caught on a zoom video

um, you're doing it wrong.

Old people skin. I just brush up against something and it tears the skin.

6. Being noticed a lot in your 20s and 30s by women in "their" 20s and 30s, but getting into your 50s, and NOT being noticed by women in their 20s and 30s anymore.

Addendum: Any comment related to "getting older/growing old" qualifies as a "worst thing that can happen to a man."

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1. Debt. I've never paid a penny of interest in my life, a policy that turned out superbly. Paying for things just once is bad enough.
2. Mismatched mate. My old lady loves to fish, hates to shop, and actually studies how to please a man at the highest levels possible, continually improving her, uh, moves. The one before her just about destroyed my life - the first 2 weeks were a blast, then not so great.
3. Marriage. Kudos to those of you who did well with that silly, archaic institution but for many I've known, it's gone terribly. It's one thing to break up and yet another to have to get a divorce.
4. Ineffectiveness. I'm extremely effective. When I walk into an office to tend to a matter, I always carry the attitude that I could steal the guy's wife if I really tried. The men I know who feel ineffective suffer badly.
5. Incuriousity. Far too many men I know don't reach out to learn more. They don't look things up. They are largely educated by Facebook and memes via a pathetic little phone screen. They watch either Fox News or MSNBC exclusively and don't feel the need to expand their scope.
6. Vision. It's awful being used to seeing fine all your life, then it changes. Bummer.
7. Marginalization. I come from a family in which kooky women smother their unfortunate men, rendering them errand boys and caretakers with little clout. My household is strictly co-leadership, with whoever is best suited for a particular situation taking the helm and the other gliding into an elite first mate role.
8. Hurried. Not having enough time is a cursed existence. There are few things sweeter than having too much time on your hands.
9. Connected. I pity people who are terrorized by their phone all day, every day. Being out of touch is a glorious thing that is literally foreign to many now.
10. Carnal frustration. Ya gotta be kind of a pistol to even get the time of day from me, but even then I've found most women to fall short. Way short. Upon dumping the last albatross 19+ years ago and getting a gal who performs at apex levels, my quality of life went through the roof. "Anytime, anyplace, any way." We're now on a mission to get my bell rung in all 50 states and 13 Canadian provinces and territories. 45 down, 18 to go, and 9 more tasks/acts have been added to the original list for a total of 630 goals, 292 of which have been attained. It's the coolest thing ever done in human history. Yes, that's a bold statement, but I wholly stand by it.
11, Boredom. I'm a musician, writer, and reader, so I never get bored. The cure for boredom is curiosity. The cure for curiosity is death.

You only get one life (uh, sorry, Hindus). Make the very, very most of it.

Interestingly, the above heavily applies to the ladies, too. We're not nearly as different as many fancy.

Losing mobility/dizzyness/fear of falling.