First Date Ideas in Downtown Boston: From Quirky to Classy

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Posted March 3, 2014 by Aimee Ortiz in Downtown Boston
End your night at J.J. Foley's for a fun and casual time.

Though some may not want to admit it, first dates can be great. The feeling of a new relationship or friendship, a new person, and new possibilities is an exciting prospect!

First dates are also often dreaded because people feel the need to be the best versions of themselves, whether it be their personal presentation or the activity they choose. Here are some first date ideas that run the gamut from quirky and casual to classy and elegant. Downtown Boston provides you with all the opportunities to help you have a great time and get you that coveted second date.

Quirky

Morning: CityGolf

The morning is one of the more interesting times for a date, so take a swing at proposing something unexpected. Forgo a typical brunch and head over to CityGolf for a virtual experience on some of the most beautiful fairways in the world.

Spend the morning practicing your swing at Pebble Beach or St. Andrews—the choice is yours with over 30 different courses to choose from. CityGolf’s simulators also track your ball and swing, giving you instant feedback on how you can improve. Spend the morning bonding while working on your swing—if you’re a golfer, there’s nothing like shaving strokes off your game to bring you together.

Afternoon: Lot F Gallery

Lot F Gallery is one of Downtown Boston’s hidden gems. Open from 12:00 to 4:00 p.m. on Saturdays and by appointment, this gallery offers an intimate view of artwork from both local and national artists. Take your date to check out some of Boston’s emerging artists at the gallery or, even better, check with the gallery to see whether there are any special events coming up. New exhibitions tend to make for smooth conversation, and getting your date’s take on the work you’re viewing could provide some key insight as to whether a second date is in the offing.

First date ideas should be fun and simple—take a walk through Downtown Crossing.

Walking and enjoying Boston is a great way to start a first date. Photo Credit: Aimee Ortiz

The gallery is located on Pearl Street, which is an ideal location for your post-art show stroll to dinner. Enjoy the beauty of Boston’s architectural history and walk the small, snaking alleys. You just might find a little piece of history around every corner.

Night: J.J. Foley’s Bar & Grille

J.J. Foley’s Bar & Grille is considered a Boston classic. The original South End location opened in 1909, with the Downtown venue opening in 1959. Don’t let the simplicity of this Irish pub fool you—it’s one heck of a venue. Traditional Irish food, quaint booths, and a jukebox create a perfect ending to an off-the-beaten-path type of date.

While you’re at J.J.’s, be sure to try the fish and chips (I suggesta liberal dose of malt vinegar on both) and a timeless Guinness. After all, it’s a first date, so you might have some jitters. J.J’s encourages a pint, you know, for courage.

Play a competitive game of darts with your date. It will get you chatting while the bartender serves up some Irish nectar!

Classy

Morning: Boston Athenaeum

Another “think outside the box” first date idea involves the Boston Athenaeum, one of the city’s oldest and most important cultural institutions.

With its library of over 400,000 volumes and its equally impressive collection of 100,000 rare books and art, the Athenaeum is sure to keep you and your date busy for hours.

Before you arrive, coffee in hand, check out the Athenaeum’s events page. Perhaps there is a book discussion or a film that you and your date can enjoy together. Even if there isn’t, just perusing the aisles of this magnificent building is enough to bring out your best conversations.

As a first date idea, try picking out books out for each other. It’s a great way to see what he or she thinks of your tastes, and it could open the door to either deeper conversations, or a quick exit to the relationship.

Afternoon: Boston Opera House

For a classic and romantic experience, consider the Boston Opera House. Built with opulence and luxury in mind, the Boston Opera House opened its doors back in 1928 as the B.F. Keith Memorial Theatre.

A date at the opera must be well planned and thought out. Will you and your date attend a matinee or an evening performance? What sort of show would your date like? Do you want to see the Boston Ballet or perhaps find tickets to the upcoming musical “The Book of Mormon,” which is returning to Boston in April? Take these questions into consideration before you buy tickets. Don’t hesitate to check availability as soon as you have all the particulars in order…this is one of the city’s most popular venues.

Night: The Last Hurrah

Located inside the famed Omni Parker House hotel, The Last Hurrah stands to be the perfect place to end your evening. With supple leather upholstery, beautiful mahogany details, and a martini menu that would make James Bond swoon, The Last Hurrah will bring an intimate and lavish touch to your date night that cannot be matched anywhere else.

While you sip on an Elderflower Sidecar (Hennessy V.S., St. Germain elderflower liqueur, and fresh lemon coupled with a sugared rim), make sure you and your date look at the bar’s view of the Freedom Trail and its historic photo collection. It doesn’t get more classic Boston than that!

No matter what kind of first date ideas you’re looking for, Downtown Boston gives you the opportunity to talk, learn, laugh, and have fun with someone new.

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