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Age: 40

Since separating from her husband, one Boston-area alumna in her late forties has had numerous dates and even a long-term relationship. For those over 45, the world of dating is more complicated for a variety of reasons, ranging from the logistical to the emotional. For many, returning to that scene after divorce or the death of a spouse means adapting to new modes of social networking, such as Internet dating sites. For everyone older—and less energetic—facing the risk of rejection takes courage, creativity, and resilience: in short, more personal effort. That is how the game is played after

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But it has nothing to do with baseball.


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Thanks for subscribing! Look out for your first newsletter in your inbox soon! He up! Looking for date ideas in Boston?

An advice columnist sets out to find out which city is better for finding romance

With so many cool things to do around the Hub in normal times, the only limit is your imagination. Here are an assortment of options that pair shared treats—awesome food or a spa indulgence—with a fun activity, all while keeping logistics in mind. If none of these strike your fancy, make a night of it by pairing one of the best things to do in Boston with a meal at one of the most romantic restaurants in Boston.

Just remember: if nothing else, get out of your comfort zone, dress up a little, and—for one entire evening—get off your cellphone. Show off your culinary cred by hosting a date at Boston's coolest gourmet destination. The contemporary culinary hub boasts a tantalizing assortment of curated food offerings, two slick bars and lots more. There are enhanced safety protocols and plenty of seating—both indoors and on a lovely, spacious patio.

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The courtyard is decorated in seasonal blooms, offering a central space where nature is the art. Third Thursdays have themed events, with resident and visiting artists in all disciplines. The cruises feature a three-course dinner and music, usually a singer and guitarist playing a low-key set of rock and pop standards.

After dinner, a DJ takes over so you can embarrass yourself on the dance floor.

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Harbor viewing on the outdoor deck is a must-do both before and after dinner. On weekday evenings, the Starlight Dinner Cruise is a shorter trip than the weekend three-hour cruise. This hip trattoria has a s feel, especially with the amber glow of globe lights. Nosh on handmade pastas and Italian-inspired dishes alongside tasty cocktails.

Sit side-by-side at the vintage central communal table, or huddle by the Scandinavian white tile, double-sided fireplace. Dishes are deed to share, or not, and the super sexy desserts are not to be missed.

The 13 best boston date ideas

After dinner, stroll to Central Square and check out a band—or a comedy night or belly dancing—at the Middle East. Seriously though, Mount Auburn Cemetery is a boston date spot. Set on 72 verdant acres, this National Historic Landmark—the final resting place for numerous famous names—is also an arboretum and wildlife sanctuary watch out for the wild turkeys in spring; they get a little tetchy while guarding their young. The secluded dell is a quiet spot with a lovely pond, and nearby Washington Tower has inspiring views over the city and beyond.

All that walking builds a healthy appetite for a superb dinner at Harvest. Tucked in an alley between Brattle and Mount Auburn Streets, this Harvard Square couple is one of the top restaurants in the area, and boasts a beautiful culinary team. Dine at the chic bar, in the main room, or outside on the secluded patio, which has a fireplace. Work your way over to Fort Point Channel and do the return stroll along the Rose Kennedy Greenwaywhich pairs manicured nature with notable art installations.

Follow those urban explorations with a journey through the world of Trillum's innovative, intriguing beers. The separate, Asian-inspired treatment room is equally spacious and has natural light. The experience includes a personalized adult ritual or ature spa treatment. For a mid-week date to remember, the Coit Observatory at Boston University datings free public viewings looking Wednesday nights throughout the year—cloud cover permitting.

The hour-long viewing parties with professional astronomers last about an hour. Then, you are ready for a night of drinks and dinner massachusetts the street in Kenmore Square.

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Start with a perfectly-made cocktail at The Hawthornethen couple next door to Eastern Standard. This longstanding American brasserie offers a varied menu sure to please even the pickiest of eaters. For massachusetts active date idea, bike the mile route from Bedford to Fresh Pond in one go. Consider adding a wager on the home stretch, turning the return journey into a race. If you're riding one-way to Fresh Pond, finish with dinner at Freepoint Kitchen.

Located in the hip Freepoint Hotel, this hidden gem features a beautiful patio with a fire pit and dating star gazing, plus a bar menu bosting looking Manhattans and other creative cocktails. Head to A4cade for a night off from being an beautiful and eating healthy.

Escape into game land at this vintage game arcade, then rest your digits while enjoying cocktails and boston comfort food. The team adult Area Four pizza operates this speakeasy arcade is filled with classic arcade games GalagaMs. Pacman and favorites like skeeball and foosball. When it comes time to refresh and renew the wardrobe, Newbury Street continues to offer the best and most beautiful parade of stores in Boston.

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Stop in at Tea Forte, the Concord-based tea merchant, which turns your daily tea fix into a romantic ritual. For apparel, try some his and hers preppy glam at Ted Baker. Start at Arlington and shop all the way down to Hereford, and then head to Sonsie for drinks or dinner.

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This Back Bay mainstay has a beautiful low-lit dining room that exudes a bistro feel. Table 12 is known as the engagement table; here couples often take things to the next level by popping the question. The AMC is connected to the Ritz-Carlton, so ask the staff to point out the secret door leading into the movie palace. Never been to the ballet?

This stylish take on the Japanese izakaya includes a lavish sushi bar. The bar includes banquettes that are possibly the best seats, especially for watching the astute bartenders craft amazing drinks. Good riddance! Temps are dropping, but there are still plenty of cool things to do, albeit carefully, while safely getting some fresh air. Among the best things to do year-round in Boston are plenty that take place away from the elements, but given the current conditions, options like awesome hikingsunny beachesfun cruisesand outdoor dining should move to the top of your list.

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Given the ever-changing nature of government rules and restrictions, not everything listed here might be open to the public — remember to always confirm plans with the venue in advance. No matter where your interests lie, you can always find something to get excited about in the Hub. The best things to do in Boston run the gamut—from seriously fun to awesomely educational.

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Looking for culture? Spend a day exploring Boston museums. You've come to the right place. There are tons of amazing restaurants in Boston that highlight the city's rich and diverse culinary landscape. We've searched all across the city to assemble this list of the best things to do in Boston.

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Follow it and never get bored here again. Done something on this list and loved it? You can also find out more about how Time Out selects the very best things to do all over the worldor take a look at our list of the best things to do in the world right now. Go to the content Go to the footer Close Boston icon-chevron-right Boston.

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