By Nia Divris

That small town feel can make dating tough on the apps, with the feeling (or fear!) that you truly may have dated, or swiped on, everyone. So many Bostonians suffer from dating fatigue from the apps and want to meet their partner more organically. Matchmaking, of course, is a great option for outsourcing your search to the professionals and making more organic connections, but it’s possible to play matchmaker yourself a bit by simply knowing where to look.

Lucky for you, we Matchmakers know where all the best women are hiding. And as small as Boston may feel, there are so many amazing little corners of our city and so many organic ways to meet new amazing people.

For the single 20’s, it’s heading to Southie or downtown bars, but when it comes to the 30-something singles, it’s a different ballgame.

Some of the best spots where you get a little Boston nightlife without the loud bars or clubs are hotel bars.

The Liberty Lobby Bar is unmatched when it comes to wanting to have a “night out” with class.
It’s casual chic with soaring ceilings and noise levels where you can have a conversation over some cocktails. Fun fact - The Liberty Hotel was originally constructed as the Charles Street Jail from 1848-1851 and you can still find those jail cells in the basement of the hotel.

In the heart of Back Bay, Oak Longbar + Kitchen located in the Fairmont Copley Hotel is another favorite of ours. This sophisticated hotel bar serves American dishes with craft cocktails while gorgeous chandeliers dangle above you and floor to ceiling windows looking out into Boston - the perfect spot to strike up a conversation with somebody new in a classy environment.

If hotel bars aren’t your thing, and you’re more of an “outdoorsy type”, there’s a new spot where you can enjoy some sunshine called Tall Ship in East Boston. This laid-back floating bar is unique from most of the Boston spots, located on an antique 245-foot-long sailboat with tables shelling out seafood, bites and creative cocktails. There’s even a turf next to the ship where you can play cornhole, giant jenga, or order from a plethora of food trucks! Pro tip – you can even catch live music on select nights.

If you live for the sunshine and water, another great option is Landing on Long Wharf.
It’s a fully outdoor patio bar located in the Seaport on the waterfront. Serving fun drinks like fishbowls, Coronaritas and margs, this is the spot to cool down on a beautiful sunny day.

If bars aren’t your thing and you’re more of the fitness junkie, there are plenty of ways to meet a like minded partner who shares your love for activity. The fit-fam community in Boston has skyrocketed over the past few years with no shortage of places to break a sweat. You can join Equinox, a higher scale gym located in the Seaport, Financial District, Midtown Boston & Back Bay. Boutique fitness remains huge, and a great way to connect with new people. Take a Barry’s class, the original high intensity interval training mixed with weights and treadmill with an unmatched community feel.

Another great option that won’t dig into your pockets can even be a long walk in the picturesque public garden. There are gorgeous bridges, paths, willow trees and benches to just sit and take it all in. It’s the best place to find like-minded singles who prioritize health and movement.

With the beautiful fall season upon us, there are tons of places in Boston to explore the fall foliage. A long walk down the Charles River Esplanade, hopping over to walk the Cambridge side of the Charles River, The Boston Common, The Arnold Arboretum right outside of Boston in Jamaica Plain and so much more.

No matter which neighborhood in Boston you’re in, no matter what season, there’s always something exciting to do where you never know who you could bump into organically.

The best thing you can do is venture to new places that resonate with you and your values, hobbies and interests. I always tell my clients they won’t meet anyone new sitting on their couch. Venture out to places that excite you, make eye contact, smile, and remember confidence is everything when approaching women “in the wild”!