DH didn't tell me about an inheritance he received while we were dating, and I appreciated that. He told me a week before the wedding when I was freaking out spending 1k on an after wedding meal (we got married in a very cheap hawaiian beach wedding, the entire thing cost 5k, with our airfare). I had close to 6 figures in student loans, he did not. When he told me, I wasn't pissed, I was relieved because both he and I knew we were marrying for the right reasons.
We talked finance stuff before marriage all the time, the plan to pay off my loans, living and eating on the cheap etc. I was much more frugal then he was, and I think he appreciated that. We just didn't discuss his net worth. I agree with the others on here, talk finances, just not net worth until you are SURE. And with your parents, they may be upper middle class, but that doesn't mean they have assets. DHs dad made 300k plus a year and is completely broke living off of credit cards in his retirement.