Why are you posting this? FHL

I wouldn't feel that bad, its more awkward but I mean unless he already told you they had died then asking about them shouldn't make you feel awful, how are you supposed to know unless you're told.

More like **** his life. I'm sure he understands.

Where is the "I Agree, His Life Sucks" button?

At least you hadn't made a dumb joke without knowing or something. Simply asking about it isn't really that big of a deal. Express your condolences and move on from it. You were going to find out eventually.

It's not like you knew. It's unfortunate and really bad luck, but there was no way for you to read his mind. If the date went well, I'm sure he'll forgive you.

People think this is a sore subject, and I agree it can be if it is fresh, but people make "your mom" jokes to my husband lots, and then if they find out his mom passed away really young, they feel super bad. He doesn't tell them at that point because ten he feels guilty for them feeling bad when it really doesn't bother him. People have no way of knowing.

Not your fault OP. How were you supposed to know any of that?

I'm pretty sure he won't hold it against you. You can't know unless you ask.

How could you have known OP? I'm sure he totally understands. You were simply being sweet and trying to spark more conversation. Don't worry about it. Hope there's another date!