Can a person be certain they are going to Hell

As has been written many times, not even the greatest saint can be certain that they are going to Heaven, on the other hand can someone be certain that they are going to Hell? if not then how can they go there out of their own free will if they are not certain they are choosing it?

Saul Alinsky, noted radical atheist, was certain. In fact, he chose hell. From an interview with Playboy magazine:

ALINSKY: … if there is an afterlife, and I have anything to say about it, I will unreservedly choose to go to hell.
PLAYBOY: Why?
ALINSKY: Hell would be heaven for me. All my life I’ve been with the have-nots. Over here, if you’re a have-not, you’re short of dough. If you’re a have-not in hell, you’re short of virtue. Once I get into hell, I’ll start organizing the have-nots over there.
PLAYBOY: Why them?
ALINSKY: They’re my kind of people.

Yes. I think some people can be certain.

I had a co-worker who always used to say “I’m going straight to Hell”.
I honestly couldn’t tell if she meant it.
To be fair, she was kind of a strange person in a lot of ways.
But it used to really creep me out.

That sounds quite scary, I hope she is better now.

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I don’t think people can be certain because most of the ones saying, “I’m going to Hell” don’t seem to have a good understanding of what Hell is or how it feels. They seem to think it’s going to be some kind of interesting or even fun place.

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Some might say they are certain but I don’t believe that. Everyone has until their dying breath to repent and be saved and nobody knows in advance what they will do.

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