In the Words of MyCheekyDate
Welcome to the Boston edition of Cheeky Thoughts! We know that finding the perfect first date spot can make all the difference. Whether you’re wandering through historic neighborhoods or enjoying a trendy new venue, we’ve got you covered with some of our favorite Boston locales.
🏙️ Back Bay
Oak Long Bar + Kitchen — Nestled in the historic Fairmont Copley Plaza, this elegant spot is perfect for a classy, laid-back first date. Enjoy craft cocktails and a warm, inviting ambiance that’s perfect for easy conversation.
Newbury Street Café — For a more casual vibe, take a stroll along Newbury Street and stop into one of the cozy cafés. It’s perfect for a relaxed coffee date with plenty of people-watching.
🌊 Seaport District
Lookout Rooftop and Bar — With stunning views of the Boston Harbor, this rooftop bar is a fantastic spot to impress your date. Enjoy the breeze off the water and a laid-back vibe that’s perfect for a memorable first meeting.
Legal Harborside — For a quintessential Boston experience, head to Legal Harborside. It’s a great spot to share some seafood and enjoy the waterfront setting.
🎨 Cambridge (Harvard Square)
The Sinclair — Located in the heart of Harvard Square, The Sinclair offers live music and a cool, laid-back atmosphere. It’s perfect for a date night that’s a little out of the ordinary and full of personality.
Tatte Bakery & Café — For a more low-key date, Tatte is a beloved local favorite. Enjoy a pastry and a coffee in a cozy, charming setting that’s perfect for easy conversation.
🌳 South End
The Beehive — This bohemian spot in the South End is known for its live jazz and eclectic vibe. It’s a great place for a date that’s full of character and a little bit of adventure.
Barcelona Wine Bar — If you’re in the mood for tapas and a laid-back, romantic vibe, Barcelona in the South End is a fantastic choice. Share a few plates and enjoy the cozy ambiance.