10 Out of the Box Date Ideas

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Winter 2025

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Going for a coffee date can be, frankly, boring. Sure, you can have deep conversations and find synergy with your date that way, but why not at the same time make it a fun, memorable experience for the both of you! That’s where out-of-the-box date ideas come in. They can alleviate the pressure of having to come up with clever conversations, and the activity allows you to just enjoy being together. And as I like to say, with regards to entrepreneurship, “You don’t go into business to do business; you go into business to do repeat business.” The same is true with dating. Your goal, ultimately, is to keep them coming back, and one way to go about doing that is showing your them that you’ve put some thought and time into the date.

Show Your Philanthropic Side

This is a sure-fire way to find out about your date’s compassion and empathetic character — by indulging in activities that help others. You can separate the wheat from the chaff quickly if they complain it’s not fun or interesting enough. Start by giving blood. You can share conversation while in line, while you’re laying down on the gurney, and while enjoying post-procedure nibbles. See if there’s a nearby retirement home where you can volunteer. Have fun playing board games with those who would very much enjoy new friends to keep them company. Just don’t expect them to go easy on you!

Private Classes

Try a private dance class. Learn tango, hip-hop, cha-cha, polka, swing, line dancing, or even disco! Don’t be afraid to step on each other’s toes, since that’s all part of the fun. Yes, get a good laugh by how clumsy you (or they) are. There’s the added bonus of some physical intimacy here, too.

Fresh Produce Picking

 Prepare to get your hands a bit dirty and crouch in the muck a bit. It might be inglorious for some — in which case, stick to the easy stuff like apple picking — but otherwise, if the both of you like to connect with Mother Nature and pick fresh, organic food, and want the farm-to-table experience, this is a perfect experience for tree-huggers.

Sand and Spray

Take to the beach and bring some fun gear: Frisbee, inflatable ball, sandcastle building toys… and be a kid again! Or rent a kayak or canoe and have a romantic boating experience across the lake.

Sail Away

 More on the water theme: take a romantic harbour cruise at sunset or charter a yacht and share some champagne together.

Roller Skating Outdoors

 Skating at the ice rink indoors is an old stand-by for dates. For some people, going in circles gets monotonous. So, try renting roller skates or even investing in a pair for future dates. Find a local boardwalk, park, or empty parking lot to skate around in.

Flower and Butterfly Gardens

Every medium-to-large city has an arboretum, butterfly conservatory, or flower garden to visit. For example, the Toronto Botanical Garden is a lovely place to take in the vast array of flora. It can be a quiet, romantic, and fascinating stroll through nature. If there are no plaques to identify the plants and flowers, download a plant app and discover what you are seeing together.

Projector Nights with Friends

 In nice weather, have your own “outside movie theatre” in your, or a friend’s, backyard. Rent a laptop-compatible movie projector and project the streaming image onto the back of the house. Sit back on some deck chairs, pass around the popcorn, and enjoy. This can be a regular date idea or for groups.

Guided Conservation Hike

 A typical date might include dinner and a movie for two, but for the same price, you can hire a professional nature guide to take you through conservation lands. It’s a private time for the two of you, a learning experience, as well as (potentially) a memorable date. With luck, you’ll get a glimpse of birds and animals, or maybe even pluck fresh berries, nibble on wild-grown nuts, or find plants to boil for tea!

Enjoy Local Sports

 Do you know if there’s a little league game near you? Or a softball tournament nearby? Don’t underestimate the joys in watching amateur sports — you might be surprised to see good players and even a good game. The best part? It’s free! Cheer on and root for the players.

Dave Gordon | Contributing Writer

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