wishing you hatzlocho. I dated my husband in Israel and got engaged here there is nothing like dating in Israel.
You can go to a hotel near Mamilla (not Mamilla hotel they don’t let you in and it’s a bit spooky for dating, dark etc) try Waldorf Astoria or Citadel and then walk to the Kosel at the end together if you want depends if he is comfortable bumping into ppl. You can separate last minute incase he meets his friends from yeshiva.
I really recommend the dating game ‘perfect matches’ btw if you get stuck for conversation in hotel lobbies, it’s fun but also gets you to talk about real things that you might not know how to bring up otherwise.