My W told me she wanted me to plan dates, arrange child care, etc. She thought this would make her feel like I cared, given the amount of effort that takes.
I asked myself the same questions that your H asked you.
I was afraid of looking foolish and feeling embarrassed. I was never comfortable "planning" an evening. What if she didn't like it? What if it was not romantic?
Now, with all that said. Maybe your H responded that way for similar reasons as I did. Maybe you could arrange the first and afterwards tell him "this is the type thing I'm talking about".
I felt the pressure because I had no ideas on what to do. In the end, it may not have been that important but I worried about it. My W would have been happy shooting pool but I never knew that.
