Keep it active.
Do something that is active, physical, and fun. Think of things like kayaking, walking a nature trail, wine tasting, a museum or exhibition visit, or visiting neighborhood or community festivals (there are a zillion of these in late spring, summer, and early fall).
Street Events.
This should take 60 minutes, which is a good first date timing…unless you two really get along immediately or you're just having too much fun. This is an excellent opportunity to get to know each other. Spring, summer and fall are great times for street fairs, art fairs, holiday celebrations, etc. You can meet at a booth for something warm to drink, an ice cream, etc. You can walk and look at whatever is being displayed. Then you could return to work, go home or simply leave. In addition, this setting affords great people watching, booth browsing and inexpensive but tasty eats.
Outdoor Special Event.
Many antique car shows, vintage airplane shows, etc., are often open to the public without admission or a small admission cost. They'll be advertised in your local paper. Usually, they're staged in open air malls, near picturesque locations or airfields. If you like the event, suggest meeting there for a specific time limit. You'll have fun things to watch, and the cost will be minimal.
Do something neither of you have done before
Pottery class? Swing dancing lessons? Hiring a moped & driving out into the country? Who knows, but it's nice to share an experience that is new to both of you!
Spectator Sports.
You can watch bike races through the neighborhoods. You can go to a local high school or college to watch sports – which will be priced accordingly. Or, you can take a walk on the beach. Then, after 45 minutes or so, you can go get a cup of coffee, tea or something cool to drink.
Playground date
Slides are exciting. Monkey bars are fun. Swinging side by side is totally awesome, & you can have a contest as to who can swing higher. (Hint: if you are younger you will probably win this one. Older people, I have learned, sometimes feel motion sick on swings. Definitely one of the downsides of maturity.)
Video game arcade date
What could be a better first geek date? Girl in high heels & those weird shoot-em-up zombie games. Or whatever. (How impressed would you be by a your date kicking immense zombie butt?) But everyone likes air hockey. Don't they?!
Pretend to be tourists
Do the stuff you've never done because, well, you've always lived here. Wear a baseball cap, khakis & a bum bag ("fanny pack") for a feeling of real authenticity, & don't forget to take plenty of photos!
The really long one-way walk
No rules except that you just have to walk for a really long time in one direction & not turn around. When you're really exhausted or you hit the ocean, it's time to go back. Catch a taxi or a bus or something to ease the pain.
Take a dog for a walk
It doesn't have to be yours, or even hers. Borrow your friend's dog! They're adorable & fun & will give you something to talk about if you get stuck. Plus, people will come up to you & say, "Cute dog", & you can beam at each other like proud parents.
Go to the beach
Take music, towels, a big floppy sun-hat or two & enjoy the day. Build sandcastles, put sunscreen lotion on one another, go swimming & then travel home together as the sun is setting, relaxed & happy.
Medieval Times
Eating with your hands, handsome knights, silly hats? How cool is that?
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