Date Night Ideas in Toronto

Setup.Two bikes and two helmets (the park's trail rules require cyclists to wear one, and electric bikes are not allowed), full water bottles since there is no running water in the park, and binoculars if you own a pair. The entrance is at Leslie Street and Unwin Avenue. The park is open all day on weekends and holidays but only from late afternoon on weekdays, so check hours before you go.

1. Meet at the Leslie Street gate and agree on one rule: phones stay in bags until the lighthouse.
2. Ride the main multi use trail out slowly. Whoever spots a bird first gets to name it, correctly or not; more than 300 species have been recorded here.
3. At Lighthouse Point, stop, look back across the water, and each find your own neighborhood in the skyline.
4. On the ride back, slow right down through the meadows and cottonwood woods and stop wherever the birds are loudest.

Talk about:This whole place was built out of the rubble of old buildings. What is something good in your life that got built out of a mess?

Setup.Allan Gardens is at 160 Gerrard Street East, between Jarvis and Sherbourne. Admission is free and the conservatory is open every day, but check hours before you go. There is no coat check, so wear layers you can carry.

1. Start under the dome in the Palm House and stand still for one full minute, just breathing the warm air.
2. Walk the other houses: tropical, then orchids and bromeliads, then the arid house with its agave and aloe.
3. Each of you picks the one plant you would take home if you could, and has to defend the choice in one sentence.
4. End in the temperate house, which changes with each seasonal flower show, and find the koi pond.

Talk about:What is a place, anywhere, that feels like summer to you even in the middle of winter?

Setup.Harbourfront Centre runs Summer Music in the Garden, free concerts on Thursday evenings and Sunday afternoons through the summer, and the series has now run for 25 seasons. The lineup changes every year, so check the schedule before you go. Bring a blanket and a light picnic.

1. Arrive half an hour early and walk all six sections of the garden, each named for a movement of the suite, from the Prelude to the Gigue.
2. Before the music starts, share one pair of earbuds and listen to the Prelude of the first cello suite, then put the phones away.
3. Find a spot near the performers and let the concert be the whole plan.
4. Afterward, walk the waterfront trail while the light goes and pick one song from tonight to keep as yours.

Talk about:If the two of us were a piece of music right now, which movement would we be in: the slow one, the dance, or the big finish?

Setup.Evergreen Brick Works is at 550 Bayview Avenue, down in the Don Valley. A free shuttle bus runs all year from Broadview subway station. The market runs every Saturday morning, outdoors under the pavilions from spring to fall and indoors through the winter, so go early. Bring a tote bag and a rough budget.

1. Take the free shuttle from Broadview station down into the valley.
2. Walk the whole market once before buying anything. Then each of you picks breakfast for the other.
3. Eat, then walk the paths of the Weston Family Quarry Garden, where the old clay quarry is now ponds, meadow and forest.
4. If you still have energy, pick up the Beltline Trail, which passes the site, for a stretch before heading back.
5. Buy one ingredient neither of you has cooked with and plan dinner around it.

Talk about:What did Saturday mornings look like in the house you grew up in?

Setup.Take the subway to Dupont station and walk north to the foot of the steps where Spadina Road meets Davenport Road. Spadina Museum sits at the top, beside Casa Loma. The house is shown by free guided tour only, tours run on a schedule and the house is not open every day, so check times before you go.

1. Climb all 110 steps without stopping, counting out loud together if it helps, and catch your breath at the top.
2. Join the next free tour of Spadina Museum. Pay as much attention to the people who worked in the house as to the family who owned it.
3. Walk the museum's restored gardens afterward; the grounds are open daily.
4. Stroll past Casa Loma on Austin Terrace, each claim a tower, then take the steps back down slowly.

Talk about:The house shows a family meeting the telephone, electric light and central heating for the first time. What piece of technology changed how the two of us talk to each other?

Setup.Guild Park and Gardens is a public city park at 201 Guildwood Parkway in Scarborough, a long way east of downtown, so give it a whole afternoon. By transit, the 116 bus runs there from Kennedy station. Wear shoes with some grip and bring water.

1. Start in the gardens south of the old inn and treat it like a treasure hunt: each of you finds one carving you would put over your own front door.
2. Sit in the Greek Theatre, built from the marble columns, capitals and arches of the old Bank of Toronto. Take turns standing on the stage and saying one thing you are proud of from this year.
3. Look for the Osterhout log cabin, lived in by 1861 and one of the oldest buildings in Toronto.
4. Walk the trail along the top of the bluffs and stop at the lake lookouts, staying well behind the ropes.

Talk about:If you could save one piece of a place from your past that no longer exists, what would it be and where would we put it?

Setup.A restaurant doing weekend bottomless brunch. Reservations.

1. Order water alongside everything, important.
2. Eat the eggs first, the cocktails second.
3. Walk for at least 30 minutes after.

Setup.An indoor skydiving facility. Closed-toe shoes, comfortable clothes.

1. Watch the safety video twice, listen.
2. First flight is the hard one.
3. Second flight, you actually look around.

Setup.A renowned BBQ joint. Get there early, the good stuff sells out.

1. Order one of every meat, sharing is the whole game.
2. Skip the chairs if there is a queue. Take it to a park.
3. Walk for at least 30 minutes after.

Setup.A farm-to-table restaurant within driving range. Booking essential.

1. Drive out late morning.
2. Order whatever the chef recommends.
3. Walk the farm or grounds afterwards.

Setup.A pair of indie record shops. A budget, one record each, no more.

1. Each picks one record for the other based on cover and sleeve only.
2. Reveal at the till of the second shop.
3. Buy them. Walk home.
4. Listen to both end-to-end that evening, in order.

Setup.A beach with legal bonfire pits, most coastal cities have at least a few. Wood, kindling, a lighter, marshmallows on sticks.

1. Arrive before sunset. Build a small fire.
2. Eat dinner around the fire, sandwiches or cooked-on-stick foods.
3. Marshmallows for dessert.
4. Put the fire out fully before leaving, beach rules matter.

Setup.An antiquarian or used bookshop in a literary city. Cash for small purchases. A budget.

1. Each picks the section they would never otherwise visit.
2. Spend 30 minutes there. Pick one book.
3. Reveal at the till.
4. Read at a café for 30 minutes before walking on.

Setup.A baseball, basketball, hockey, or football game. Cheap seats, they are cheap for a reason and that's fine.

1. Get there 30 minutes before first pitch.
2. Hot dog and a drink each.
3. Stay through the seventh-inning stretch.
4. Walk to a bar near the stadium afterwards.

Setup.A live podcast recording in town. Tickets in advance.

1. Get there early to chat with other listeners.
2. Stay for the audience-questions bit.
3. Eat at a place near the venue afterwards.

Setup.A train ticket to a town 60–90 minutes away. A return ticket for after dinner.

1. Take the early train. Coffee on board.
2. Walk one full loop of the town in the morning.
3. Long lunch in a place tourists do not go to.
4. Bench in the afternoon, then home on the slow train.

Setup.A state park, national park, or large nature reserve within 90 minutes' drive.

1. Pack: water, snacks, layers, a small first-aid kit, two thin towels.
2. Walk a moderate trail, 4–7km usually fits the day.
3. Lunch on a bench or rock with a view.
4. Eat dinner at the closest small-town restaurant on the way home.

Setup.A roller rink with an adult, disco or late session. Rental skates, thick socks, and pads if the rink offers them.

1. Do the first two laps holding the wall. Nobody is watching you.
2. Skate one lap holding hands. It is harder than it looks, and funnier.
3. Each of you learns one new move: skating backwards, a crossover, a slow spin.
4. Finish on the slow song lap, then share something fried from the snack counter.

Talk about:What were you like at twelve, at a birthday party exactly like this one?