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Top 5 Places to Meet Boston Singles This Fall

Fantasy football, pumpkin-infused brews on tap, and the return of college students to the city, all signs point to Boston gearing up for fall. New England is the quintessential place to enjoy seasonal foliage, especially while arm-in-arm with a would-be love interest, and autumn is one of the best times to get out there and meet other singles in Boston. As expert dating coaches at LunchDates, we know the hottest spots to meet singles whether you’re twenty-two or sixty-two, and we highly encourage you to take advantage of all the upcoming fall festivals, seasonal beers, road races, and local gatherings. To help get you started, here are five of the top fall destination spots in Boston to meet singles:

For Singles in Their 20’s…

South of Boston is where it’s at! Coppersmith in South Boston or Lawn on D are the spots to be for professional millennials. Watch the sunset on the roof deck on a late September afternoon. Sipping a local seasonal brew is a great way to enjoy your Saturday while mingling with other singles. Feeling a little competitive? Lawn on D offers free games, including ping-pong and cornhole, as well as a number of events. TIP! Ask another group to a friendly game of Bocce. If you’re shy, get the most outgoing person in your group to do the talking first. It’s a great way to break the ice and meet some new people!

For Singles in Their 30’s…

Seek out local Oktoberfest events. Sample local brews at the annual Harpoon Brewery’s Oktoberfest or combine your love of running and drinking with Cambridge’s annual 5k Road Race. These large festivals pull from a diverse crowd. Lots of music, beers on tap, and German cuisine will have you feeling the fall vibes. Get a group of girls and guys to attend together. You’ll bump into lots of different types of people. TIP! Polka dance, anyone? Even if you don’t want to dance, asking someone if they ever have (or know how to) is a great ice breaker.

For Singles in Their 40’s…

Check out Charlestown. Pier 6 offers an outdoor waterfront patio and a great view of the city. Warren Tavern, a historic tavern established in 1780 in Charlestown, offers a piece of local Boston history (yes, George Washington and Paul Revere both drank here!), as well as live acoustic music. TIP! Get the most out of a warm fall afternoon via a water taxi to soak up the full experience of Boston on the water.

For Singles in Their 50’s…

Hit the high-end Boston restaurant scene. Bristol Lounge or Strip by Strega are both posh spots for Boston locals and hotel guests. Great martinis and a busy night scene provide the perfect backdrop to chatting it up with new friends. Although these trendy spots come with a higher price tag, you’ll appreciate the clientele they draw from. Singles in this age group normally are well situated, financially secure, and wanting a much more sophisticated exchange of conversation. TIP! Go in small groups (2 is ideal for women) and don’t sit with your backs to the bar. Sure, your feet will thank you, but it’s hard to get a conversation started with the back of your head. Work the room.

For Singles in Their 60’s…

Art, wine & fun! MFA Singles Night is a great choice. Singles in their sixties want to mingle without the stress of walking up to someone at a bar. The bar scene can seem awkward and unnatural. The Museum of Fine Arts offers a great way for singles of all ages to casually mix and mingle with an upscale backdrop of modern art. The first Friday of each month offers singles signature cocktails, music, and an array of great appetizers for the evening. TIP! You have to be proactive and talk. The MFA gives you the perfect opener to discuss a painting or your favorite artist.

Date Proactively With a Professional Matchmaker

These Boston hot spots are a great way to meet singles, however, not everyone is comfortable meeting people this way. I recommend to just go out and enjoy yourself. Hunting for singles from spot to spot for the best eligible guy or girl can be exhausting (and too much pressure!). If you feel like online dating is not for you and you want a more “natural” way to meet other singles, Boston offers plenty of options to get out there and socialize. But sometimes that’s not enough. I advise my clients to use every resource available to them, including working with a professional matchmaker.

Boston natives understand that you have to make the best out of a beautiful fall day. The season is short. Winter comes quickly behind it. Love is the same way. You have to be proactive when it comes to dating, especially now with all the dating apps out there. Take advantage of the season and your time by giving us a call at LunchDates. Who knows? You could be hopping around the city with a great new guy or girl come Halloween!

Aimee Burke is a Boston dating coach and matchmaker at LunchDates. Aimee specializes in date coaching for singles in the Boston area. She also serves as an executive matchmaker and recruits professional singles for her clients.


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