Dating in Boston in Your 20s: How to Find Meaningful Connections

Should you date in your 20s? 

Why shouldn’t you? While it is true that dating in your 20s can seem difficult to combine with work and studies, it is also true that this may be the perfect age to have fun while dating. Whether you are looking for a long-lasting relationship or just a few casual meetups, dating in your 20s is a great way to get to know yourself better. 

As you leave your teenage years behind and enter adulthood, playing the dating game is a nice way to meet other people while learning what you want in a relationship. Also, in the meantime, you may come across other people living in Boston and open the doors to other forms of networking. The key is finding where to meet women in Boston (and men too!) and selecting the right place for a date. Why not give it a try?

Is dating in Boston easy when you’re in your 20s?

Many people in Boston say that it may harder to date here than in other cities, but many others don’t agree. So who’s right? We believe that it totally depends on your experience and how you manage dating! It may be true that people find it hard to date in the middle of building their professional careers. But we all need leisure time to do hobbies and see other people, and dating can perfectly fit that gap too.

Where to meet singles in Boston

Dating apps that really work 

Lola Dating

With little time available in between classes and work, time spend on dating apps should be preciously cared for. That’s why mainstream dating apps sometimes fail: untruthful connections, endless swiping, and no real-life dates only lead to wasted time. 

Fortunately, there are several dating apps better than TInder! With Lola, daters are first matched based on their availability to meet in person over the next 5 days! So you will get to talk with one another only after you have agreed to have a date. This way, you won’t waste time chatting with people who are only on apps to fool around. Besides that, you will have the chance to provide feedback about your date to improve your dating pools for upcoming opportunities. How cool is that?

• Best recommended locations: 

You and your date will get to choose where to meet, but if you are looking for a middle ground with a relaxed dating environment, take a look at Lola’s events, where daters can meet in a specially dedicated safe space.

• Who will enjoy it: 

Lola is all about dating. For real. So if you are a 20-something with no time to lose, download Lola and set up a date for this same week!

Casual coffees with a relaxed atmosphere

• Best recommended locations: 

Tatte Bakery & Cafe: A nice bakery for a brunch or afternoon tea date, with plenty of delicacies and treats for all tastes, in the heart of Cambridge.

Capital Once café: A coffee with a futuristic twist to lay back while enjoying a neat atmosphere in East Sommerville.

Caffé Nero: An Italian-style cozy café with lots of pastry and viennoiserie options in the South Boston Waterfront.

• Who will enjoy it: 

Great for students and young professionals looking for a laid-back atmosphere where they can relax in the middle of their hustle and bustle.

Bars with a fun atmosphere and good food 

• Best recommended locations: 

Center bar: A great spot with a great setting, Center bard is located within the Encore Boston Harbor hotel. With a retro style, it’s great for a night of fancy drinks.

The Locke Bar: A classic nighttime bar for drinks and lots of practical food options, like finger food, dips and burgers, to taste some delicacies while meeting new people.

Parla Bar: A cozy bar with mixed styles to cater to all tastes, in the heart of Boston downtown.

• Who will enjoy it: 

Ideal for a proper first date where you can decide to have just a couple of drinks or chat the night away. Bars may be some of the best places to meet single men in Boston! 

Outdoor spaces to enjoy the best natural spots 

• Best recommended locations: 

Charles River esplanade: A Boston classic to take a walk along the river to enjoy the sunset together.

Belle Isle Marsh Reservation: Ready to spend some time alone in the middle of natural escape? 

Fresh Pond Reservation: A spot offering tranquil pathways along the Fresh Pond filled with natural life.

Orient Heights Beach: A shore location to get a view of the port, ideal for any weather.

• Who will enjoy it: 

Great spots for nature lovers who are looking for relaxed environment where there are no distractions to take you away from deep talk.

Museums and art galleries 

• Best recommended locations: 

Museum of Science: Are you looking for an original location that will surely trigger lots of interesting conversations? You’ve found it! Only for nerdy ones.

Harvard Art Museums: These museums offer a collection of pieces from several art movements, ideal for all types of art lovers.

MassArt x SoWa: An art gallery with changing exhibitions that combine painting, sculpture and even artistic clothing designs. 

• Who will enjoy it: 

Ideal for those looking for a place that takes them out of the routine and allows them to have some new experiences.

Best tips from locals 

Take advantage of Boston’s seasons

Boston is a city that offers lots of different experiences based on the season, so take advantage of its great variety of options in order to enjoy a truly original date together.

Consider daytime dates 

In the middle of work and studying, meeting late at night can be discouraging for some, so keeping your options open to arranging lunch-time dates can be a great idea.

Don’t overlook day trips or getaways 

If you have already met for a few dates and seem to be building a connection together, hopping on a ferry or bus for a day away can be great to escape routine together.

Overcome Your 20s Dating Challenges with Lola Dating

Ready to go head-first into dating? Then it’s the right time to download Lola. Create your profile and tell others when you are free for dates. You will soon have a date assigned for the next five days! No more canceling dates due to overloaded calendars. You will only match with people who are also available when you are. 

FAQs

Dating in 20s vs 30s: what changes? 

Most people in their 20s are just looking for fun! Though there are some people who may want to settle down, that is way more common in your 30s. It is good to keep that in mind in order to keep your intentions clear from the very beginning and avoid disappointment later on.

Is Boston good for your 20s? 

Sure! Boston is filled with university students coming from other cities, so it offers a wonderful mix of experiences to collect during your 20s.