This is our sixth post in a series of advice column-style blogs entitled “Asking for a Friend.” For more information on the series and to submit your own questions, click here!

By Victoria Barry

That’s a great question! I can see that we’ve got a lot of daters at StoryHeights (which we love). This here will be a completely practical post, but if you’re looking for some real advice on biblical dating, check out our What Even is Dating series here.

I thought about scrapping the title you currently see and making this one “50 First Date(Night Idea)s” – but there are not 50 date night ideas in here and they aren’t all geared towards first dates. But let it be known that I still remember Drew Barrymore’s career!

What I can give you though, are 12 (that’s right, 12) date night ideas in Boston and the surrounding areas, and I’m going to do you a solid and categorize them by area and include a range of price points. Think of these as a jump starter or guide to get out there and explore – whether you’re married and dating, single and going out with friends, or even actually going on a first date (eek!).

The options below are really just a taste — Boston has a wealth of activities to offer, and
If you’re ever stuck, one of my favorite resources is thebostoncalendar.com. So many good things happening! That being said, let us know if you’ve got any more ideas for good date nights in the comments below!

Boston Proper

1. Dinner in the South End followed by live music at Wally’s (South End; $$-$$$)

A classic. Good food, good music – what else could you need for a good date? The South End has an endless amount of restaurant options, but some of my favorites for that date night vibe are SRV (Italian), Gaslight (French), and Barcelona (small plates). A plus is that Wally’s is within walking distance from pretty much any South End restaurant and offers free live music every night! The perfect hole-in-the-wall spot to cap off your night.

2. Breakfast at Tatte followed by a nice dose of culture (Fenway; $-$$)

Hear me out on this one – even if you think you might not like art museums, Boston has some top-notch ones. Not to mention there are few better conversation starters than “what do you think?” while staring at a piece of confounding art together. My suggestion is to start off with a nice breakfast or brunch at Tatte in Fenway, then walk on over to either Museum of Fine Arts or the Isabella Stewart Gardner Museum. I’d recommend the MFA if you want the classic art experience; ISG if you’re looking for a cozy-extremely-rich-persons-house-that’s-filled-with-famous-art experience.

3. Lunch at Galleria Umberto followed by a North End jaunt (North End; $)

Ok, whether or not you go on a date, you should try this pizza if you haven’t already. It’s $1.85 per slice and probably one of the best Sicilian-style pizzas you’ll taste outside of Italy. Plus, it has that whole walk-in, casual, family-run feel and is a great stop for a meal. They’re also only open for lunch, so this may have to be a Saturday venture! I’d suggest following it up with a walk along the harbor, a romantic swing at the Rose Kennedy Greenway park swings, and maybe even a pastry if you’re feeling crazy! (Modern is the best, don’t @ me)

Cambridge/Somerville/”The North”

1. Visit the deCordova Sculpture Park and Museum and pack a picnic (Lincoln; $-$$)

What can I say? Art is a great date foundation. More than that though, this sculpture park is beautifully well-maintained and the perfect place to spend a morning or afternoon lazing and enjoying each other’s company.

2. Kayak along the Charles River (Cambridge; $-$$)

A classic Boston-area activity. You can rent a couple of kayaks (or a *couples* kayak) from Charles River Canoe and Kayak’s Kendall Square location and take them up and down the Charles for sweeping views of Boston’s skyline and unforgettable memories. Maybe just don’t touch the water.

3. Dinner at Rosebud followed by a movie at the Somerville Theater (Somerville; $$)

Head on over to Davis Square for this one! Take in dinner at Rosebud American Kitchen first. Half of the restaurant is in an old converted dining car and the other half is in a cozy, wood-paneled dining room – all of it is candle-lit and the perfect ambience. Once your full of good food and pie, walk over to the Somerville Theater for a throwback-cinema feels

Newton/Natick/MetroWest

1. Dinner in Chestnut Hill followed by a Showcase Super Lux movie ($$-$$$)

The Street at Chestnut Hill has an array of food offerings, but this one is all about the Showcase Super Lux. Although it is a solid $10 more than every other movie theatre it’s well worth the price. This theatre is all about luxury, so go and be spoiled with offerings like a seat warmers (or coolers), pillows and blanket for the movie, and full service for all of your drinks and snacks (no concession stand here, folks). And if you’re not really feeling Shake Shack or Tendergreens, there’s a Davio’s Italian Steakhouse that serves meals inside of the theatre to make your experience EXTRA fancy.

2. Explore Garden in the Woods (Framingham; $)

Garden in the Woods is a native plant botanical garden and also the headquarters of the Native Plant Trust of New England. Drive out here for a day of exploring local New England wildlife complete with gardens, wetlands, ponds, and unique habitat displays! Learn a little bit more about the land you live on, together….so romantic.

3. Visit a pick-your-own farm! (Millis – and all over; $)

A favorite New England activity, and a good date idea to boot. Find a farm that’s local to you (honestly they’re a dime a dozen around here) and make a day of it. Most farms have an in-house café or food stand that make great breakfast or lunch spots! One of my favorites is Tangerini’s Spring Street Farm in Millis. After that, look at what’s in season and get to picking. Summer berries are a lot of fun, or if you’re looking for the classic Fall date, go for the apples! Have fun helping each other pick the best ones and taking lots of cute pictures for when you’re Facebook official…

Quincy/Braintree/”The South”

1. Hiking at Blue Hills Reservation (Milton; $)

This one is straight foolproof. Blue Hills has something for everyone, no matter their level of physical skill. Pick your path, explore some nature, pack some coffee, play fun games in the outdoors – just be a couple ‘a kids again.

2. F1 Racing at X1 Boston (Braintree; $$-$$$)

Got a need for speed? Or just a need to do something exciting and slightly terrifying to make both of you feel less nervous? This could be your place. If you’ve ever wondered what it’s like to do F1 racing, X1 Boston in Braintree can hook you up. Grab your date, tackle a new adventure together, and if all goes well, maybe stick around for billiards and a bite to eat afterwards.

3. Grab a bite to eat and explore World’s End (Hingham; $)

World’s End is a 251-acre park and conservation area in Hingham that is a great place to explore, walk trails, and spend time near the water. I’ve never been, but I hear great things (AKA read them on the internet). Another place I’ve never been to but that got 127 5-star reviews on Yelp is a sandwich shop nearby called Bloomy Rind – you should check out both of these things and let me know how they are! I hear they make for a great date.

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