It’s a Date: Some Ideas for a Great Boston Date

The best piece of dating advice my mom has ever given me is, “dates are more fun when there’s an activity.” Don’t get me wrong, I love going out to a nice restaurant or cozying up at the movie theatre but there’s truly no better way to get to know someone than by engaging in an activity together. So, stop making a mental list of possible conversation topics or worrying about the perfect outfit; take the pressure off with any number of creative date activities here in Boston. Here’s a short list of ideas to get you started…

For the Active and Adventurous:

A Day on the Mountain: Whether you’re a boarder or skier, or tubing and snowshoeing sound like more your speed, there are a few places nearby for you and your date to make a day of it. Nashoba and Wachusett are decently close to Boston if you have a car. If you do not have a car try the Weston Ski Track (accessible from the Green Line) or sign up with the Boston Ski and Sports Club (BSSC) and they’ll do the driving and planning for you.

Ice Skating: You don’t have to leave the city for this one. Whether you’re a beginner, novice, or the next Tara Lipinski there’s no better way to experience the city in the winter time. Try the Frog Pond on the Common (may get crowded on weekends), Larz Anderson Park in Brookline (bonus: there’s great sledding nearby—why not make a day of it?), Community Ice Skating at Kendall Square (this rink is on the smaller side), or the rink at the Charles Hotel in Harvard Square.

Bowling: For a retro feel on the other side of the Charles check out Sacco’s Bowl Haven in Somerville or, if you’re looking to stay in the downtown area, try Kings Back Bay. Both have bowling, pool, and a restaurant in case you work up an appetite!

The Night Life Scene:

Lucky’s Lounge: A Frank Sinatra themed restaurant and bar, Lucky’s is the one for the cool cats. With live music most nights and a unique atmosphere you won’t soon run out of things to talk about—you might even find yourself out on the dance floor!

The Cantab Lounge: I believe the Cantab Lounge to be the best-kept secret in Cambridge. Whether you’re into funk, bluegrass, or rock, this homey dive is the where you’ll find the real deal. My favorite is the Bluegrass Pickin’ Party on Tuesday nights—last week the floor turned into a dance party and I’ve heard it does the same thing for Thursday night funk! Highly recommended.

For a Rainy Day:

A Museum: Show off your cultural know-how with a day trip to one of Boston’s many museums. Visit the Isabella Stewart Gardner Museum on the third Thursday of the month for their extended evening hours or check in at your local branch of the Boston Public Library for discounted passes. Also, try the Museum of Science (you may say I have 6 year old boy syndrome but the K’nex exhibit looks mighty cool), the MIT Museum (sweet holograms and Rube Goldbergesque machines), the new Art of the Americas wing at the MFA, and others.

Arts & Crafts: For a hands-on approach to activity based dating try painting your own piece of pottery—it’s not just for kids! Try The Clayroom in Brookline, Made by Me in Harvard Square, or Clay Dreams in Arlington.

For the Sports Fan:

Winter Sports: If all else fails you know the sure way to any Bostonian’s heart is through sports. Get tickets to a college hockey game, visit a local bar for apps, a beer, and the big game (see Chris Klein’s Where to Watch for great bar ideas), or spring for Celtics tickets—I promise, if your special someone is a true Bostonian you can’t go wrong with sports!

If I missed anything please leave a comment below, I’m always in the market for new and creative ideas. Best of luck!!

Leave a Reply

Your email address will not be published. Required fields are marked *