I'm glad to hear about the fun evening out with adults, the hangover isn't so good! I think we all overthink on here, trying not to overthink is really hard and not something I have got a handle on yet. I'm naturally a thinker, I like to understand how things work and am used to always analysing everything. Trying to switch that off and just accept things is difficult! Maybe stupid people are lucky, lol.
Has he been to your house alone before? Do you have an alternative dog sitter? I don't know, the paying for you to go away is a bit weird. What is his LL? Is he a controlling person? There could be LOTS of explanations for his behaviour, including some negative ones. How do we stop the mind reading?