1Bar Le Mal Nécessaire
Cocktail bar·Quartier international·$$·30s
A tiki-style cocktail bar ranked among Canada's 100 best bars, with DJs every night and service until 3 a.m. on weekends. Reserve early in the week; on Fridays and Saturdays after 8 p.m. it is first come, first served.
1015 rue Saint-Alexandre, Montréal, QC H2Z 1N9 · Takes bookings
2Upstairs Jazz Bar & Grill
Jazz club·Downtown·$$·All ages
A cosy jazz club with live sets most nights, usually at 7 and 9:30 p.m., and dinner if you want it. Cover charges are modest, and the music does half the talking on a first date.
1254 rue Mackay, Montréal, QC H3G 2H4 · Takes bookings
3The Comedy Nest
Comedy club·Downtown (Atwater)·$$·All ages
Montreal's original English stand-up club, on the third floor of the old Montreal Forum across from Atwater metro, with shows most nights. Laughing together takes the pressure off, and there is plenty to talk about afterwards.
2313 rue Sainte-Catherine Ouest, 3rd floor, Montréal, QC · Takes bookings
4Montreal Museum of Fine Arts
Museum·Golden Square Mile·$$·All ages
The city's major art museum, spread over several pavilions on Sherbrooke Street. It stays open until 9 p.m. on Wednesdays, so an evening visit and dinner nearby make an easy midweek date; book your time slot online.
1380 rue Sherbrooke Ouest, Montréal, QC H3G 1J5 · Takes bookings
5Cinéma du Parc
Cinema·Milton-Parc·$·All ages
An independent cinema showing art-house and international films, with special series like midnight screenings and talks with filmmakers. A film and a walk up to the Plateau afterwards is a classic Montreal date.
3575 avenue du Parc, suite 6100, Montréal, QC · Takes bookings
6Schwartz's
Deli·Plateau Mont-Royal (Boulevard Saint-Laurent)·$·All ages
The famous Montreal smoked meat deli on the Main. Expect a queue and shared tables, but it is cheap, quick and a fun, unpretentious date, especially if one of you is new in town.
3895 boulevard Saint-Laurent, Montréal, QC · Walk-in
7Olive et Gourmando
Café·Vieux-Montréal·$$·All ages
A much-loved bakery café in Old Montreal, open every day until 4 or 5 p.m., with great sandwiches and pastries. No reservations, so go mid-morning and follow it with a stroll through the old streets and the Old Port.
351 rue Saint-Paul Ouest, Montréal, QC H2Y 2A7 · Walk-in
8Café Olimpico (Mile End)
Café·Mile End·$·All ages
A classic Italian café in the Mile End, open daily from 6 a.m. to midnight, with strong espresso and a busy terrace in summer. Perfect for a low-pressure first meeting, before or after a bagel down the street.
124 rue Saint-Viateur Ouest, Montréal, QC · Walk-in
9Parc du Mont-Royal and the Kondiaronk Lookout
Park and viewpoint·Mont-Royal·$·All ages
The mountain in the middle of the city, with wooded paths up to the Kondiaronk lookout and its view over downtown and the river. Free in every season: a walk in autumn, skating, snowshoeing or sledding in winter.
Chalet du Mont-Royal, 1196 voie Camillien-Houde, Montréal, QC · Walk-in
10Pointe-à-Callière, Montréal Archaeology and History Complex
Museum·Vieux-Montréal·$$·All ages
A museum built on the site where Montreal was founded, with exhibitions on the city's history and temporary shows. Open Tuesday to Sunday until 5 p.m.; adult tickets are $30, and the Old Port is right outside for a walk after.
350 Place Royale, Montréal, QC H2Y 3Y5 · Takes bookings