Improv asylum early show then dinner at trattoria il panino. Grab a bottle of wine from golden goose and go to the small park on lewis wharf near Paul Revere park. Watch the rabbits and look out on the water. 

Please add Drink 40s behind dunks

Oooh good list! Thanks for sharing

Saw a new one on here today: pet a sloth at Animal Adventures in Bolton

For first dates, I would grab a scoop at Tosci's and walk up + down Mass Ave, just talking.

The various buildings are prompts for early discussion: "This place has good sushi, do you prefer hand rolls or hand jobs? That place is called Little Donkey, have you ever performed in a donkey show?" etc...

It's low risk and low commitment for both people. Always in public, so relatively low fear. Easy for either to bail at any time if things aren't clicking.

Sacco's Bowl Haven in Davis Square

Lucky Strike in Somerville. You are also close to shopping stores nearby as well to do something before or after, if you have time, if you start earlier.

Brighton Bowl at American Flatbread. It’s candlepin bowling.

I still like Kings Back Bay location.

Urban Wild in Charlestown.

Bowling at Urban Wild. Also- this is my go-to when looking for fun date nights:

https://www.thebostoncalendar.com/

Don’t write off walking outside. Wear the right clothes and get 2 nice travel mugs. Fill with your favorite hot bev, then spike that shit for a giggle. You’re not driving. Go hard on the spike. The city is magical and so different on a winter night.

Those were my favorite dates when I was first married and we were young and house-poor in the South End. I think we walked every inch of the city over the course of those first few years. One night we loaded our pockets with like 20 nips of cordials that someone had left at our house, low proof dessert-y stuff like Godiva liqueur, and whoa boy between the alcohol and the sugar we had a blast.

Bowling. Candlepin if you’re a local or want to be. Regular balls if you’re gonna whine about candlepin.

Classes at Dave’s Fresh Pasta are fun (and delish)!

I enjoyed this https://www.fourhandedillusions.com/
also can always do crafts glasses - like making things out of glass, ring making, cooking classes, ice skating

also you can still walk outside and make stops for drinks/coffee/dessert/etc... when you get cold

That’s amazing you have the chance for a few date nights—definitely make the most of it! ❤️ Winter can make things trickier, but there are still plenty of fun, unique options beyond dinner & movies. Here are a few:

🍝 Cooking Class Date Night – Instead of just going out for dinner, why not make it together? We host interactive cooking classes in Downtown Boston where you can learn to make fresh pasta, dumplings, or even a full Italian dinner. It’s hands-on, fun, and perfect for a cozy winter date! (Happy to share details if you're interested!)

🎭 Theater & Live Shows – American Repertory Theater in Cambridge or small indie performances at Central Square Theater.
🎷 Live Music at The Beehive – Great for jazz & cocktails in a cool atmosphere.
🛶 Nighttime Gondola Ride on the Charles – Yes, even in winter, they have cozy blanket-covered rides!
🥂 Secret Speakeasies – Try Offsuit or Next Door for a hidden bar vibe.
🎨 Art & Wine Night – The Paint Bar or a pottery class at Clay Lounge in Cambridge.
🕵️ Escape Room Challenge – Boda Borg in Malden is super interactive & fun.
🌿 Indoor Botanical Garden Escape – Isabella Stewart Gardner Museum has an amazing indoor courtyard that feels like a mini getaway.

If you’re looking for something interactive, fun, and cozy for winter, a cooking class could be a great option! Let me know if you’d like details. 😊

If he gets off work at 7 and is already home I’d venture to guess you guys can be anywhere you want by 8-8:30 maybe even 7:30 which isn’t a late night especially since you have the combined age of half the people in here. You’re basically going out at the time most people go out on dates lol.

But if it’s later which apparently to you guys is 9PM you can grab your AARP cards and see if there’s an escape room still open, or you could walk around Faneuil hall or the north end.

Comedy clubs and concerts often don’t have their best performances start til 8-9 or even 10.

Movie theaters have late night showings especially the smaller ones. Bowling is open late and drinking isn’t necessary to have fun.

I think you guys will find a lot to do and have a lot of fun!

If he’s here for the weekend Sowa Winter Market is always fun to attend. Great food and drinks and you can get your holiday shopping done at the same time!

Local museums sometimes have late night events, the ISG, MFA, and the ICA.

Roof top Igloo at the Hotel Envoy.

Cafe Victoria is open till midnight. Wally's is a live music place.

Just fuck him

Decordova Museum in Lexington

Outdoor stuff (SUP, kayak, hike, pickleball, minigolf, TopGolf)

Volunteer

WooSox games

Go to Bow Market and play some pinball at Pop’s Pinball Parlor

Learn to sail in the Charles or the Harbor.

Candlepin

Art and architecture tour at the Boston Athenæum. Walk the Freedom trail. Gardner museum. The Harvard Art Museums are free.

75 Chestnut St., just off Charles St. Is very nice and not expensive.

Nightshift Brewing has a beer garden on the Esplanade. You can see the food truck schedule here. You would need to be 21+, they check.

Lolita is nice. Just don't go on a weekend night.

I would do a picnic honestly. Impress her with your charcuterie board skills. A blanket, a bottle of wine, a charcuterie board, and snuggles while watching the sunset….

Ma Maison on Cambridge St off Beacon Hill is a small French bistro that is not expensive for the area. It's very French and could be an option. That being said, I think the picnic option suggested above is the best.

It's such a nice day, I would just do a walking tour of the city since you said you're relatively new. Maybe follow the freedom trail from North End to Boston Common and then picnic in the park.

Kimball Farm in Westford. Play mini golf, eat from the grill and get ice cream.

Walk around the Arnold Arboretum, esplanade, public gardens?

Get kicked out of the barking crab

Cambridge is having a block party

There is a beautiful Italian restaurant in Dedham just over the West Roxbury line. It had a sister restaurant in Brockton

Muse Paint Bar in Assembly is a lot of fun -- they even have paint your pet nights!

Snowport at Seaport starts next Friday. That could be fun.

https://www.boston.com/culture/events/2021/11/03/the-seaport-will-once-again-transform-into-snowport-a-holiday-wonderland/

Stay in and get some Boston Cream Pies

Giulia’s in Cambridge is very good and the next door is honeycomb creamery l.