I went out with my bashert 5 times before we got engaged. we alternated between 2 hotel lobbies. If you know that is where you will be going, and think you will run out of things to say, prepare a list beforehand of topics you would like to talk about! No, it won’t be taking away from being “yourself” or being “natural”. it’s called being prepared. When you are on a date, you are on the spot and under pressure. If you have a general list in your head of 10-20 topics you could bring up, you will be able to avoid most awkward pauses and have a pleasant conversation. Worked for me!
Also, by the third date, we wanted to get to know each other a bit better, so we brought along a deck of cards with questions (don’t remember the name of the game) – who is your role model, what is your fondest childhood memory, etc etc. We also took a look at a book describing different personality types (dont remember the name, its quite popular) and tried to explain which type best described us.
By the fourth date, the shadchan put pressure on my (not-yet) husband to take me out somewhere more interesting and suggested miniature golf. We were in the car set to drive there, when we discovered that we both were really not interested, so we went back to the hotel 🙂
The point is, if you are prepared with topics and questions, hotels are not evil, can even be a pleasant atmosphere. And don’t let the shadchan/best friend/parents pressure you into going somewhere more exciting – discuss it with your date!
oif simchos!