Would this be... stupid?

First, I am curious as to what would motivate you to double down on what is described as a failed relationship...?

Second, the context of the shit that happened and what broken means to both of you is important.

Not a good idea to ask that because he'll think you doubt his affection. Heck, even I do. To me it seems like you just wanna put the ring on him and you will try any trick possible to get there.. for who knows what reason.

If you were both happy with each other, marriage isn't that big of a deal. Just being together would be enough by itself. I'd recommend that you talk this through instead and see where your motives are, both yours and his, cause I can't imagine this heading in a good way.

Some men will be insulted, some won't. You know him better than we do so only you know which he is.

No harm in asking.

Do it !!
Both my sistas did
Mostly because the men were getting way to comfortable lol
And also to find out if they were wasting their precious time with them .... it’s a win win thing ...

Just tell him you'd like to be married one day, if that is your wish.
How he responds is either going to encouraging or a red flag.

Why would you want to marry someone who you had a failed relationship with ?

If it is broken, you should get married regardless who asks.

I feel like it’s just always safer if they ask you 🤷🏽‍♀️

If you’re not sure they’ll say yes don’t ask

It’s not stupid and it certainly isn’t insulting.