Folks are giving some great suggestions here. Let’s rewind just a bit, though. What do you think your date would like to do? If you’re not sure, that’s ok, but if you do, I recommend using that knowledge to your advantage. (Obviously, it should also be something you would like to do.)

I also suggest if you decide upon an outdoor activity that you make a backup indoor plan in case the weather stinks on the day of your date. Trying to make a change like that at the last minute can add a lot of unnecessary stress for you.

Here’s something that I haven’t seen suggested yet:

Worcester scavenger hunt

There’s a date night option here that’s $20/per person. I’m not sure what your budget will bear, but this could be fun, and would certainly be different than a lot of things you might do. The tickets are good for up to 2 years, so you won’t be out the $$ if the weather is gross.

Also, I have some unsolicited advice. When you go to pick up your date, whatever you decide to do, bring them a flower. Not a whole bouquet, just one flower is enough. It doesn’t matter where you get it, whether it’s from a florist or the grocery store. People in general don’t give flowers anymore, and underestimate the value it will have to your date. The mileage you’ll get from it is wild. Your date will tell everyone they know about it. It also means that if, Dog forbid, something doesn’t go as planned, they’ll still look upon you as potential second date material, should you decide you’d like to go out again.

We’re all rooting for you!