Right person, wrong time

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I shouldn't have gotten high and asked to suck his dick.

Choosing the university near my home village.

If you're still in secondary school, only apply to units far enough away that your parents will have no choice but to let you move out.

YOU of all people should know

Thanks OP, now the curiosity is killing me

Should've told her.

If it wasn't for that horse I wouldn't of spent that year at college

If only I had stayed for seconds on bacon that day

Simultaneously it's saying things but also not saying things.

Shouldn't have looked

Should have been more brave that one summer.

I should've known he was an iPad kid

leaving the womb

Choosing the easier path when it really mattered

Panicked at the wrong moment.

Shoulda realized we only liked shiny and new things

the way I ruined my nostrils, among other things

I should've said "No, Abso-fucking-lutely NOT".

Veterinary syringes are "veterinary" for a reason

I should have never gone to that bookstore.

I met the All Thing but I listened to the voices

The event

This happened some time ago, but I did something kinda bad/cringe and afterwards I thought "I really shouldn't have done that" and it haunts me to this day. That is my biggest regret.

Knowing what I don't know

Let the dog in the neighbors open door.

All the lies, the damned lies, and for what?

First day on Earth

My biggest regret is my biggest regret. Duh.

I should have fought

Taking Elsie to work that day in October.

I should never have bought the chips and chocolate.

I should have never deleted them.

A half measure

Okay as cryptic as possible, hmm, let me see... I encrypted everything and lost the keys?

i "retired" at 40 am now 60, my regret is not retiring sooner.

i had a near death experience at age 35, where I genuinely thought that was the end, this was the catalyst to changing my life.

I would recommend an NDE for anyone to bring into focus what is important vs what you think is important

Whoever invented Piggybacks, should carry the sins of their predecessor on his back to hell.