DH took me when picking out a ring. I think he was worried he would mess it up and I would be unhappy. Before we went, I chose 4 styles that I liked and then when we got to the store, he picked from those. He wanted to make sure I was happy enough with the size too.

I opted for one just under 1 carat that was much higher quality than the ones that were 1 carat+. It was also so much cheaper to get the one just under 1 carat. Then with the savings, I got to pick a diamond eternity band for my wedding ring instead of just a plain band.
ETA: He couldn't propose to me until his parents met my parents. It is a cultural thing. So both sets of parents (plus DH's brother) came for a weekend and he proposed in front of everyone.
Disneyland sounds nicer.
And that was a time when I took out a new credit card for a purchase. DH was a Canadian citizen and didn't live in the US, so I actually had to buy the ring.