The Five Dates You'll Go On: Seaport and Southie

“Let’s meet for drinks sometime.” It’s the death knell of any dating app conversation - a vague invitation that ultimately withers as each side volleys back with indecision. End the “I don’t care, you choose” attrition with our date ideas - uniquely tailored for all the matches you’ll meet in the Boston dating world! 

Say what you will about the booming Seaport District, but with new developments come trendy hot spots to try out in the neighborhood! This week, we’re exploring all the best date ideas on the South Boston peninsula, from brunching on Broadway to sweating it out on Seaport Boulevard. (And where better to find someone to accompany you on these dates than at Boston YPA’s Single Mingle, coming up on September 10th at the Boston Tea Party Museum?)

The date: a kid at heart.

The play: Boston Grown-Ups Museum.

After hours at the Boston Children’s Museum, the big kids come out to play. The museum opens its doors to 21+ visitors with a cash bar, music and fun themes. If your date is a sucker for nostalgia, they’ll love reminiscing on days of playing with bubbles or exploring Arthur’s neighborhood. The next Grown-Ups Museum event on September 5 will be 90’s themed. Will romance spark amid childhood throwbacks?

Second date? Stay forever young and try out Adult Night at Legoland in Assembly Row!

The date: a fitness guru who’s up to date on the latest workout trends.

The play: Seaport Sweat.

The couple that sweats together stays together! If your date is big on boutique fitness, suggest taking part in Boston’s biggest free workout series. The lineup includes yoga, bootcamp and conditioning, plus uber-trendy Booty By Brabants and Kick It By Eliza classes. Once the endorphins are flowing, you’ll surely make a lasting impression -- something to smile about while you’re sore the next day!

Second date? Call it a rest day: enjoy a leisurely walk, brunch or drinks. You’ve earned it.

The date: loves long walks on the beach and local history.

The play: Castle Island.

At the farthest reaches of South Boston stands Fort Independence, a lasting relic of the American Revolution. While it’s not a “castle”, per se, the fort’s island home attracts tourists and locals by the thousands each year. Take your date on a tour of the fort (they’re free on Saturday and Sunday afternoons, Memorial Day through Labor Day), then stroll around Pleasure Bay. The perfect end to the day? Fried seafood goodness and ice cream at Sullivan’s, a Southie institution for decades.

Second date? Take it to the other side of the harbor and check out the USS Constitution and Bunker Hill Monument in Charlestown.

The date: a thoroughly modern art lover.

The play: The Institute of Contemporary Art.

Boston’s home for contemporary art is a marvel in and of itself. Your date will love spending hours analyzing the modern works (even if your gut reaction might be “wait, what?”). After exploring the exhibit halls, take a water shuttle ride across the harbor to the ICA’s Watershed installment in East Boston - boat fare is included with your museum ticket, and the spectacular views from Piers Park are worth the price of admission!

Second date? Come back to the ICA for First Fridays, a monthly party attracting Boston’s most artistic socialites.

The date: a foodie who bemoans “basic” brunch.

The play: Lincoln Tavern’s Brunch Test Kitchen.

Brunch is far from basic at the Lincoln. On Fridays, the team unveils its newest creation from the “test kitchen,'' including zany (yet delicious) concoctions beyond your wildest dreams. Whether your date prefers sweet (Fruity Pebble pancakes) or savory (brunch meatloaf), you’ll both find something creative to tickle your taste buds. For best results, order a couple options to share. Your favorites could end up on the Lincoln’s regular brunch menu!

Second date? Pick a recipe, bring ingredients, and whip up brunch at home. Insta-worthy or Pinterest fail? Only one way to find out.

Stay tuned for next time, when we’ll be coming back at you with five all-new date ideas! Until then, have fun and happy dating!