Hey there, I’m Rebecca Cooper Traynor, a modern matchmaker with 15 years of experience helping singles in Canada find love. And trust me, after matching so many couples, I know that where you have your first date can set the tone for everything. The right ambiance, good food, and a comfortable setting can make those first-date jitters a little easier to manage.
So, if you’re in Toronto and looking for the perfect spot to impress your date, here are my top recommendations:
1. Bar Isabel – Cozy & Romantic
797 College St
Dim lighting, intimate booths, and a menu filled with shareable Spanish tapas—this is the perfect place if you want a warm, inviting vibe with incredible food and conversation-worthy cocktails.
2. Piano Piano – Playful & Charming
88 Harbord St & 55 Colborne St
A relaxed yet stylish Italian spot where you can bond over handmade pasta and a glass of wine. Bonus points if your date loves fun, flirty interiors.
3. Terroni – Classic & Reliable
Multiple Locations
Great pizza, great pasta, and a bustling atmosphere make this an easy and solid first-date choice. No pressure, just good food and conversation.
4. Café Boulud – Sophisticated & Elegant
Four Seasons Hotel, 60 Yorkville Ave
If you’re aiming for a more upscale experience, this French-inspired restaurant inside the Four Seasons is classy without being over-the-top. Perfect for making a lasting impression.
5. Chubby’s Jamaican Kitchen – Laid-Back & Fun
104 Portland St
For a more casual yet lively setting, Chubby’s delivers with its colorful decor, reggae vibes, and delicious Caribbean dishes. Ideal if you want a fun, easygoing atmosphere.
6. Oretta – Stylish & Instagram-Worthy
633 King St W & 2131 Yonge St
A trendy Italian eatery with stunning aesthetics, Oretta is great for a date that’s both casual and chic. Plus, their cocktails are always a hit.
7. The Broadview Hotel – Rooftop Views & Casual Drinks
106 Broadview Ave
If you’re more into drinks than dinner, the rooftop bar at The Broadview Hotel offers a stunning skyline view. A great way to keep things light and breezy.
8. Bar Raval – Intimate & Unique
505 College St
A beautifully designed bar with a rich Spanish-inspired menu. If you and your date are foodies, you’ll love this spot for its intimate setting and inventive small plates.
9. Byblos – Exotic & Flavourful
11 Duncan St
A Mediterranean gem with dishes made for sharing. If you want to add a little spice (literally) to your date, this is the place.
10. Paris Paris – Wine Bar Perfection
146 Ossington Ave
A laid-back yet stylish wine bar where you can sip, snack, and get to know each other in a relaxed, non-intimidating setting.
Make Your First Date Count!
Where you go matters, but how you show up matters even more. Choose a place that makes you feel comfortable, confident, and open to connection.
And if you need help with the before (finding your match) or the after (navigating the dating process), that’s where I come in! Let’s get you matched with someone amazing.
