First date ideas in Jerusalem

Botanical gardens.
The zoo.

There are many nice (and free) places to walk that are close to the popular hotels so you can meet there for convenience and then walk- Yemin Moshe/MIshkenot Shaananim area, Gan Hapa’amon, Independence Park, the Rose Garden, the large park behind the Israel Museum (officially called valley of the cross, ignore the monastery at the far end), Gan Sacher. If you are not worried about running into/meetings natives, a stroll through any nice neighborhood (e.g. Kiryat Moshe, Nahalat Shiva, Rehaiva, the Old City, etc) and stopping off in any local park you pass can also be nice on a cool evening. I suggest you bring drinks or buy in the hotel.

Zoo is not a good first date…that’s like date 3 or 4.
Winnie had a bunch of great options.
I know this sounds insane but the shadchan could also ask the girl where she wants to go. I’m usually asked for input about where to go, especially since I’ve been here for a while and many boys haven’t.

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.

People usually save going to the Kosel for when they have closed the shidduch, to give thanks to HKB”H for finding their zivug. Not a place I would suggest going on a first date, or even second or third, for that reason.