That's so sad :( don't beat yourself up OP. although it may have felt uncomfortable, the best thing to do is offer your condolences, and you can be supportive if you two decide to pursue a relationship.

I guess you can say his dad has a type

It's horrible but it's not your fault for asking. You couldn't have known

Why ask about divorce though? That's just a weird way to go. I didn't find out what happened to my best friend's dad (or lack there of) for almost two years since we became close. It's a touchy subject for most people so it's best to avoid unless they bring it up.

You were only trying to get to know him better. You did not know so don't beat up on yourself for it.

I believe you will stop asking questions about moms for few days

There's no way you could have possibly known that, don't feel too bad.

Wow that sucks. It's ok tho OP u didn't know and I'm sure he understood if not I hope u let go like Elsa

You didn't know, they're fairly harmless questions. Don't feel too bad about it. I hope otherwise everything went well though.

Oh no, his dad is probably afraid to remarry a third time.