Hey, I'm a retired Marine Master Sergeant...and I'm 40! If someone tries to take me to some museum like I'm a dinosaur, I'm gonna get pissed. I suggest you take him to some decent/popular/notable restaurants, followed by some chit chat at a quieter bar like Carney's. Put him in a position with good, creative alcohol like craft beers, and a quiet environment without drunk frat boys everywhere.
Also, without a doubt, take him to West End Elixir Co. in Northgate. That place is owned by a Marine and employs many veterans. The commandant of the Marine Corps stopped by there a few months ago. Great drinks, too.