HT Dude in the Black Hat
Let’s face it: most dates are boring artificial stretches of time in which you attempt to extract information from your partner mostly because there’s nothing better to do while sipping coffee in a crowded shop to avoid the slush in the gutters outside.
I know I’ve suggested the Tomchei Shabbos date before, but here’s a girl who had a similar idea and ran with it. I don’t really know how you manage a grocery-shopping date (Who pays? What do you do with it after? Find a kitchen and make yourself a meal?), but the idea is intriguing.
Ladies: how would you feel if a guy took you out to a grocery store?
Bad for Shidduchim 
I’ve done some “non-typical” activities on dates. It’s a nice way to get to see another side of the person. It’s true – the dressed-up-drink-Coke-in-fancy-location date is a little artificial, but IMO, I like the first couple of dates to be low-key, coffee/dinner/drinks so that I can get to know the other person enough to see if I even want to spend more time with him.
I was once in the way home from a date (I think it was a 3rd or 4th date) and we were passing my local supermarket which was going to close in 10 minutes. I knew that if I let the guy drop me off, I wouldn’t have enough time to get in my car and drive over there and I needed food for work for the next day, so I asked him if we could stop on the way home. I only needed 1 or 2 things so the whole stop was like 5 min, but he loved it that I was comfortable enough to ask. If a guy suggested that I accompany him on his Shabbat shopping trip, I don’t think I’d be so into that.
IMO doesn’t sound much different from bookstore dates. Why should it be any different? Grocery shopping is great since there’s lots to talk about. I wouldn’t recommend it if you have to do serious shopping since you wouldn’t want the date to become a chore, but to just casually stroll through.
Grocery shopping would be awesome! So much better than hotel lobby. My advice would be to go this remote supermarket (that you won’t bump into anyone in) and have FUN! Have cart races down the aisles, sample all the Hershey chocolate bars and vote on which one is best, pick a food each of you have never tried and try it, go bowling with the melons.
Plus you can tell so much about personality. Does he push the cart for you? Is he picky? Is he frugal? Is he the type that goes in and buys what he needs or is he the type that likes to look around? Is he organized-does he have a list? Does he get upset when there isn’t room to get through or someone bumps into his cart?
This definitely has potential bad4!!!! I’m loving this idea!
Swordfights with the Baguettes!
My wife and I had a few memorable moments in the supermarket but we were already married. (No, not what you are thinking, excuse me!!)
Before that, I think spending all of Shabbos together worked for us, since we were in different cities at the time. A simple get together for a few hours was not so practical, so we made our dates into personal Shabbatons. [Our first Shabbos together was our 3rd date, while the first two dates took up whole afternoon.]