Hmmm... overthinking it, maybe, but you haven't gone crazy - yet!
My two cents - don't ask him about it. Just get together in person b/c it's another opportunity to show you're doing well, and just talk about the bills, friendly-like. Then it might lead into just casual discussion about life, plans, etc. Don't bring up the OW, don't ask why he didn't want to just talk about it on the phone or via email... b/c you're really too busy to over-analyze that stuff. You're GAL and carving out a little time to meet with H but keep it casual, laid back and be your fun self!