It's Not Meguro-san's First Time - Vol. 1 Ch. 8 - Did You Not Like it?

[Av-kay]

While normally I dislike this sort of worry 24/7 trait in characters, I think its been pulled off pretty decently here. It's fun watching the MC's increasingly elaborate date prep and research, and it shows how much he genuinely wants to make things work.

and he very clearly is showing progress