Go on a tour of your local Masonic Lodge, then watch National Treasure. Have a Chopped competition to see who can make the best dish out of whatever you already have in the fridge. Follow You Tube videos to learn cooking skills that neither of you know: how to make crepes, how to poach an egg, etc.
Get dressed up and go on tours of expensive homes for sale in your neighborhood.
Find a rooftop bar that fits the vibe (whether that's cozy intimate or more of a crowded scene) and soak it in together. If you want a less stuffy environment than a dinner setting, where there's mimosas a'plenty and no pressure to stick around for the rest of the day, try going for a day date for brunch on the weekend.
For fellow angsty people, you can at least get the date out of the way and then go about your day instead of sweating it until evening.
Answer this New York Times questionnaire that might make you fall in love. Take a free class at your library or community center in something neither of you are good at.
Play farmers market ABCs: See who can find something that starts with every letter of the alphabet first.