Looking for the best Boston date ideas to impress a woman? You’ve come to the right place. Below is a list of the top first, second, and third date locations in Boston, recommended by city locals and dating experts. Before we dive in though, it’s important to understand the basic framework for a first, second, and third date.

To ensure that your first dates have the best possible chance of converting to a second date, I recommend following my date blueprint.

While I can’t give away all of the details of my first date blueprint, as I reserve that for students in our dating program, Dating Decoded, I can give you a few helpful pointers here.

First and foremost, the first date should never cost you more than $20.

I know you’re thinking I’m crazy and I live in the middle of nowhere. Wrong. I live in one of the most expensive cities in the world and I still abide by this rule. Constricting your first dates to $20 or less forces you to devise unique and creative date ideas that are more compelling than what your male counterparts are offering up.

It’s mission-critical to stand out from the competition if you want to date the most sought-after women, so I’d recommend paying close attention here.

Aside from the cost constraint, you also want to keep your first dates to less than an hour (if you’re staying in the same location).

DateCreep, or the tendency for a first date to creep on longer than an hour, leads to chemistry fizzling out. Enter the awful friend zone. I was surprised to learn this from my 100-Date Experiment, but the evidence didn’t lie.

Too much time in the same location on a first date and too much money spent, subconsciously makes a woman feel as though you are less valuable than she is. You have to make your time and money seem as though they are precious resources, reserved for a select few. Being hard to get (both in your time and money) connotes value.

Make yourself the diamond, the Tesla, the yacht.

Make your time and money hard to get and you’ll enjoy more second and third dates than ever before. If you want access to my full first, second, and third-date blueprints, check out my Signature Program.

In it, I teach all of the details of effective date planning and we co-create a list of the perfect first, second, and third date ideas specific to you, your interests, and the particular women you’re after.

Alright, let’s get to the date ideas.

First Date Ideas in Boston

First Date Ideas Boston #1: L.A. Burdick’s

“I absolutely love Harvard Square as a date destination as it has so much to offer. For a first-time winter date, my suggestion would be to go to L.A. Burdick’s and grab the most delicious hot chocolate and walk around Harvard Square. It’s always a lively place to spend an afternoon or evening for that matter.”

– Recommendation by Eva Mendes, Asperger/Autism/ADHD Specialist & Couples Counselor. Author of Marriage and Lasting Relationships with Asperger’s Syndrome (Autism Spectrum Disorder)

First Date Ideas Boston #2: CABOT’S CANDY at Harvard Square

From taffy to fudge, to chocolate-covered gummy bears, Cabot’s Candy is sure to elicit nostalgic childhood memories.

Pair this date idea with the following nostalgic questions and you’ll find the dialogue that follows easy and intimate: “What was your favorite candy growing up?” and “What is your favorite childhood memory?

To quote an interesting study, linked here, “nostalgia bolsters social bonds, increases positive self-regard, and generates positive affect.” Research shows that nostalgia can boost mood and decrease stress. It’s also likely that this topic will provide information about her family, which creates a powerful emotional connection.”

First Date Ideas Boston #3: LimeRed Teahouse

Grab a craft boba tea at LimeRed Teahouse or share a pot of fine, loose-leaf tea with your date.

Here’s how to pitch LimeRed Teahouse to a woman on a dating app:

Initial message:Have you ever had a honeycomb waffle sundae with matcha ice cream, pocky, and mochi?

Her: Nope, what’s that?

Follow-up message:The most delicious dessert ever. They serve it at LimeRed Teahouse. Want to check it out with me Saturday at 2 pm?

Her: Sounds fun, I’m in.

Your message:Great, I’ll text you the address. What’s your number?

First Date Ideas Boston #4: Kane’s Donut

Have you ever had a S’more donut? How about a maple bacon donut? Perhaps a Snicker’s donut is more your speed. Whatever you’re jonesin’ for, Kane’s Donut has it. There couldn’t be a more compelling first date for a donut lover.

Here’s how to pitch this date idea to a woman on a dating site or app:

Initial Message:Have you ever had a maple bacon donut?

Your Follow-Up Message: Kanes Donut makes them using a chocolate cake donut topped with honey glaze and caramel frosting. Then they dip them in Heath Bars and drizzle with dark chocolate. Want to taste test one with me this Saturday at 11 am?

Potential Objection: I’m on a keto diet and can’t eat sugar.

Objection Handling Message: Oh, don’t trip girl. They’re all keto-friendly. Actually, I hear the more you eat, the more 6-packs you get. 😉 It’s very hush hush though. If word got out, we’d all be ridiculously good-looking.

So…what do you say, you ready to take the donut challenge with me?

Potential Objection: I don’t know…

Objection Handling Message 2: Oh come on, you’re not gonna make me go alone are you? How sad would that be, just a gorgeous man sitting by himself, eating half a maple bacon donut, getting all the abs. Say yes, you know you want to. We can do crunches after.

#5: Thinking Cup

Ever tried a vanilla ginger latte? It’s life-changing. See for yourself at Thinking Cup, the perfect first date spot in Boston for the discerning coffee lover.

#6: Flour Bakery & Cafe at Harvard Square

Have you ever been on a cupcake date? It’s never too late to try. Bring out the kid in you by inviting your date to Flour Bakery and Cafe.

First Date Ideas Boston #7: Bon Me

Bon Me is the brain-child of Patrick Lynch and Ali Fong, winners of The Boston Food Truck Contest. The name, as well as the food they serve, is a play on the traditional Vietnamese bánh mì sandwich. The gorgeous living walls and spacious dining hall, make it a fun and low-key first date idea.

Second Date Ideas in Boston

Now that you’ve made it to the second date, you’ll want to give yourself the best chance of success. Based on data from my 100-Date Experiment and my second date blueprint, it’s best to plan a second date during daylight hours.

Your second date should also be physically active and cost no money. Following this framework facilitates a healthy degree of sexual tension, which protects you against getting friend-zoned. I go into more detail about the first, second, and third date blueprints in my Signature Program, which you can learn more about here.

Now, without further ado, here are the best second date ideas in Boston.

Second Date Ideas Boston #8: Charles River

“In Harvard Square, one could walk along the Charles River and find a bench to sit on. Perhaps with ice cream, coffee, a picnic lunch, or as a bicycle date!”

– Recommendation by Eva Mendes, Asperger/Autism/ADHD Specialist & Couples Counselor. Author of Marriage and Lasting Relationships with Asperger’s Syndrome (Autism Spectrum Disorder)

“Walk, run or ride along the Charles River. Choose the Boston side of the Charles if you aren’t into crossing the river or ride along the Charles in Cambridge on Sundays when Memorial Drive is closed. Be sure to check out the new playground on the Boston side and let the kid in both of you come out!”

-Recommendation by Kira Hower, M.Ed., Women’s Empowerment Coach, and founder of KiraHower.com

Second Date Ideas Boston #9: Stroll Along The Esplanade

“The great thing about Boston, Boston proper is small… you can walk to most places or you’re only a few T stops (what we call our subway) or a quick Uber ride from most locations. First “day time dates” (in good weather), grab a cup of coffee and stroll. Stroll along the Esplanade, great spots to sit and chat by the water or on benches watching the sailboats or the people.”

– Recommendation by Sarah Stewart, MSW, CPC Life Coach and President at SarahStewartConsulting

“Boston is a fabulous walking city. For a first date, walking the Esplanade provides sweeping views of the Charles River with Boston’s city skyline in the background.”

– Also recommended by Becca Speert, Boston’s Best Manifestation Coach & Tarot Card Reader

Second Date Ideas Boston #10: Skating on Frog Pond (Winter Only)

“Bundle up and head out to the Best Outdoor Skating Rink in the country (according to USA Today). Charming, energized and potentially romantic…you’re guaranteed a few good laughs. Adults are only $12 per person. This could also be great for Date 3 too… followed by dinner on Charles Street in Beacon Hill.”

-Recommendation by Kira Hower, M.Ed., Women’s Empowerment Coach, and founder of KiraHower.com

Second Date Ideas Boston #11: Harvard Coop

“In Harvard Square is also the Harvard Coop which is another good second date destination maybe as book lovers can browse books and also sip a coffee over a nice chat.”

– Recommendation by Eva Mendes, Asperger/Autism/ADHD Specialist & Couples Counselor. Author of Marriage and Lasting Relationships with Asperger’s Syndrome (Autism Spectrum Disorder)

#12: De Cordova Sculpture Park and Museum

“If you have a car, for a half a day type of a date, I’d suggest the De Cordova Sculpture Park and Museum in Lincoln, MA.”

– Recommendation by Eva Mendes, Asperger/Autism/ADHD Specialist & Couples Counselor. Author of Marriage and Lasting Relationships with Asperger’s Syndrome (Autism Spectrum Disorder)

#13: The Museum of Fine Arts

“You can get into some of the best museums in Boston for free if you time it right. A museum hosts an atmosphere for you to share a culturally rich experience with your date while providing unlimited conversation starters to keep you in the present moment (so you can skip the boring interview questions and really get to experience the person).

The Museum of Fine Arts earns extra points with many floors and rooms to explore so that you can keep your body moving to neutralize any nervous energy.”

– Recommendation by Becca Speert, Boston’s Best Manifestation Coach & Tarot Card Reader

Boston Dates #14: The ICA

“The Institute of Contemporary Art (ICA) provides expansive views of the Boston Harbor and is located by the Seaport, close to public transport. For a weeknight date, you can head to the MFA after 4 pm on Wednesdays, or the ICA on Thursdays after 5. Pro-Tip: The ICA offers free admission on Thursday nights from 5-9pm.”

– Recommendation by Becca Speert, Boston’s Best Manifestation Coach & Tarot Card Reader

Boston Second Date Ideas #15: The Harvard Art Museum

“If you wanna grab a coffee and explore during the morning hours, The Harvard Art Museum is free for Massachusetts residents from 10am-12pm on Saturdays. Pro-Tip: Harvard Art Museum in Cambridge is free for Massachusetts residents from 10 am to 12 pm on Saturdays (Free daily for Cambridge residents!)”

– Recommendation by Becca Speert, Boston’s Best Manifestation Coach & Tarot Card Reader

Second Date Ideas Boston #16: The Harvard Museum of Natural History

“The Harvard Museum of Natural History is open to Massachusetts residents free of cost during 9am-12pm on Sundays. Harvard Museum of Natural History in Cambridge offers Massachusetts residents free admission every Sunday morning from 9 am to Noon year-round, excluding commercial groups, with proof of residency.”

– Recommendation by Becca Speert, Boston’s Best Manifestation Coach & Tarot Card Reader

Second Date Ideas Boston #17: The Boston Commons

“If you prefer a more central spot, the Boston Commons is big enough to walk around for an hour or two. Either way, you get the romantic feel of a stroll, with plenty of natural beauty to surround you.”

– Recommendation by Becca Speert, Boston’s Best Manifestation Coach & Tarot Card Reader

“Another stroll is through the Boston Public Garden and into the Boston Common… you will have lots of entertainment and conversation starters with both people-watching and watching dogs fetching frisbees… great areas to sit, sip and chat or just stroll. I like day time dates for a first date… less pressure!!”

– Recommendation by Sarah Stewart, MSW, CPC Life Coach and President at SarahStewartConsulting

#18: The Arnold Arboretum

“A little on the outskirts of the city, in Jamaica Plain, is the Arnold Arboretum. This walk offers 281 acres of stunning landscaping. It is said to be one of the most comprehensive and best-documented living collection of trees, shrubs, and woody vines in the world. All of these walks are free and open to the public.”

– Recommendation by Becca Speert, Boston’s Best Manifestation Coach & Tarot Card Reader

#19: Explore the Mount Auburn Cemetery

“Wander the most beautiful cemetery in the country – maybe even the world! It is a breathtaking 174-acre arboretum and historical landmark. Grab a map at the front desk and meander the pathways to discover the magic of this gem nestled between Cambridge and Watertown. No picnics, dogs or bikes but bring your camera and your historian’s hat. You won’t be disappointed in any season.”

-Recommendation by Kira Hower, M.Ed., Women’s Empowerment Coach, and founder of KiraHower.com

#20: Rent a Kayak and Paddle the Charles River

“For $16/hour per adult, you can rent a Kayak and paddle the Charles River from two Boston launch points. If you launch from the Brighton/Allston spot you can paddle toward the city, with greenery on both sides, and take in the city skyline as you approach.

You have the option to paddle back when you feel like it, or end your kayak trip at the Kendal location and grab dinner and drinks in the city.

If you prefer to stay central, you can launch from the Kendal location from the get-go (right on the Red Line) and begin in the heart of it, paddling through the esplanade taking in the views of the sailboats and gorgeous skyline.

You can make a half or a whole day of this activity, with the opportunity for teamwork, being adventurous together, and making great memories.”

– Recommendation by Becca Speert, Boston’s Best Manifestation Coach & Tarot Card Reader

#21: Tango by Moonlight in Cambridge

“If you’re ready to step up, this free evening is a lot of fun and potentially very romantic! Learn together how to Tango while dancing over the Charles River by moonlight. Add dinner at Pammy’s (or Pagu in Central Square) – or a walk to nearby Harvard Square and choose from any of the great eateries for Date 3.”

-Recommendation by Kira Hower, M.Ed., Women’s Empowerment Coach, and founder of KiraHower.com

#22: The Hatch Shell

“Boston Landmarks Orchestra offers fabulous free concerts at the Hatch Shell. Bring your picnic blanket and enjoy a summer evening watching the sailboats on the Charles River.”

-Recommendation by Kira Hower, M.Ed., Women’s Empowerment Coach, and founder of KiraHower.com

There are also free movie nights at The Friday Night Flicks series, an excellent third date idea.

Second Date Ideas Boston #23: Isabella Stewart Gardner Museum

“If museums are your thing, head on over to Isabella’s House on a Thursday for some art and dinner, the charming Isabella Stewart Gardner Museum is hands down, Boston’s most romantic museum. It’s not the biggest museum in Beantown, but the house itself has an old-world feel and a central courtyard adorned with seasonal flora that is nature’s art.

Why Thursdays? The museum has a superb, seasonally-driven restaurant, the Café G, that extends operating hours up to 8 pm on Thursdays. Every third Thursday is also a themed event, with resident and visiting artists showing-off their latest work.”

– Recommended by Emily Andrews, a marketing communications specialist at RecordsFinder, an online public records search company

Third Date Ideas Boston

Now that you’ve successfully converted your first date to a second and your second date to a third, you’re ready to go all out on the third date. Now that you’ve won her trust and built a little sexual tension, it’s time to see if there’s a deeper connection.

What better way to do that than to break bread? Based on the findings from my 100-Date Experiment, third dates are most effective when they take place during evening hours.

If you’ve arrived at the third date, then you’ve likely sequenced your dates properly, starting with low-pressure, low-risk daytime dates that cost little to no money.

As such, you’re pretty much guaranteed that she’s not after your money, which is good because it means there’s a genuine connection there and that can easily lead to physical intimacy on a third date. But, you’ve got to play your cards right. The following third date ideas will help you do just that.

Third Date Ideas Boston #24: Myers + Chang

“Not all date nights need to burn a hole in your wallet. You only need to pull out all the stops on the third date or so, when things are getting to be a little more serious. If you’re out on a first date and don’t want to splurge yet, Myers + Chang has what you need: a cheap date night in Boston.

The restaurant offers three, full dinner sets for two people at a mind-boggling $45 each. The fixed menu choices have fun names such as “Long Walk On The Beach,” “Tango Lessons,” and “Netflix + Chill.” Wait till you ask your date if she wants some Tango lessons or Netflix and chill!”

– Recommended by Emily Andrews, a marketing communications specialist at RecordsFinder, an online public records search company.

Third Date Ideas Boston #25: South End, Mistral

“One of my favorite restaurants in the South End, Mistral! It is small, elegantly sexy and the food is amazing but not over the top. (I actually used that restaurant for a dating scene in my last novel Love Along the Esplanade, that’s how perfect it is)!”

– Recommendation by Sarah Stewart, MSW, CPC Life Coach and President at SarahStewartConsulting

#26: Havana Club

“Havana Club for Salsa dancing on a Friday or Saturday night is a great Boston date idea.”

Jennifer Earls, M.Ed. Career and Life Coach, & Founder of Dance With Life Consulting

#27: Lolita Cocina & Tequila Bar

“If you’re looking for a more charming setting, Lolita’s rustic interiors and dim lighting set the stage for a little PDA. With its dark and gothic atmosphere, it’s easy to lose track of time and get lost in this trendy cocina.

The Day of the Dead decor also gives the interiors a different vibe, and you might even forget you’re on a night out in Boston. Lolita Cocina offers traditional Mexican snacks with a modern-day twist.

Lolita’s also isn’t called a “Tequila Bar” for nothing, as most of the drinks are tequila-based cocktails. Step away from the crowded streets of Beantown and head here for a night of fun and shots!”

– Recommended by Emily Andrews, a marketing communications specialist at RecordsFinder, an online public records search company.

#28: Go Sailing

It doesn’t matter if you have a boat to your name or not. Boston is touristy enough to offer plenty of chances to rent one or go on a sailing tour. A sunset sail could cost as little as $60 when you book with Classic Harbor Line.

This is a super unique and romantic date idea that will show her how much she means to you.

Third Date Ideas Boston #29: A4cade

“While in Cambridge, make sure you check out A4cade for a chance to rekindle your inner kid. The adult arcade features classics such as PacMan, MarioKart, and other nostalgic games of your childhood.

Area Four hides behind Roxy’s Grilled Cheese Restaurant, and you’ll have to enter Roxy’s first before you can go to the arcade.

The good news is that you can eat a grilled cheese sandwich while playing your favorite games. A4cade also offers cocktails with a playful twist to them, featuring a colorful bendy straw fit for the child in you. For a fun and stress-free night out, you can’t go wrong with arcade games, cocktails, and grilled cheese!”

– Recommended by Emily Andrews, a marketing communications specialist at RecordsFinder, an online public records search company.

Third Date Ideas Boston #30: Figs by Todd English

“Dinner on Charles Street in Beacon Hill is a great third date location in Boston. Try Figs by Todd English.”

-Recommendation by Kira Hower, M.Ed., Women’s Empowerment Coach, and founder of KiraHower.com

#31: Pammy’s in Cambridge

“Want to find a beautiful, romantic and lively spot with great food? Look no further than Pammy’s in Cambridge. Food and service are fantastic and the atmosphere is friendly and alive – although not great for the hard of hearing.

Tough to get reservations so plan ahead. They save a few tables every night for locals so call to check. And the communal table is lovely.”

-Recommendation by Kira Hower, M.Ed., Women’s Empowerment Coach, and founder of KiraHower.com

#32: Pagu in Central Square

“Check out Pagu in Central Square for an amazing third date spot in Boston.”

-Recommendation by Kira Hower, M.Ed., Women’s Empowerment Coach, and founder of KiraHower.com

#33: Pizzeria Regina

“What better way to get to know your date than by challenging them to a board game? BoardGame Empire hosts a weekly game night at Pizzeria Regina in Allston every Monday from 6-9:30.

They bring in a mountain full of games with options ranging from the classics you love to new releases you’ve never even heard of. Feel free to grab something you know or ask their friendly host for a recommendation.

These board game savants can figure out the perfect game for you, then teach you how to play so you don’t have to spend half your date buried in the rule book. Oh, and the pizza’s pretty great too.”

– Recommendation by Jonathan Krieger, Emperor of BoardGame Empire

Third Date Ideas Boston #34: Toscano

“Take a bite straight out of Italy at Toscano. The calamari in gratella and tiramisu in a cup with a vertical slab of sumptuous chocolate are to die for, according to Boston locals.

The white chocolate blueberry tart offers a unique and enticing end to the perfect third date if you’re looking to try something new. If she’s a sucker for pizza like me, she’ll love the margarita pizza.”

– Recommendation by Emyli Lovz, co-founder of EmLovz.com

Third Date Ideas Boston #35: Pickleball!

As much as you may not want to admit it, you too have been swept up by the awesomeness that is Pickleball; and chances are so has your date.

Look third dates don’t always have to involve a nice steak and a polo. They can also be intense, sweaty affairs, where you two celebrate your win with a beer or smoothie.

There are a ton of places to play pickle in the city. One of the best is PKL Boston where you can reserve a court for $50 for the hour.

Third Date Ideas Boston #36: See A Show

The best acts in the country have to swing by Boston while on tour. Find out who you date is into and then book her surprise tickets to her favorite act. 

Third Date Ideas Boston #37: Head Over To Salem

Salem, Mass is much more than witch trials.

It’s colonial, slower-paced than Boston, gorgeous, and also the perfect spot for a third-place date.

Ship out to Salem for a Sunday afternoon and be sure to check out downtown, the wharfs, and yes the Salem Witch Village.

Keep Your Dating Funnel Full With Speed Dating

“For board game lovers, may we recommend BoardGame Empire? BoardGame Empire is a company dedicated to hosting board-game-themed events at cool breweries throughout the greater Boston area.

You can play games built by local designers at their indie board game showcase or make your own game at their design-a-game night.

For those worried this might be a little too nerdy for you, the company is dedicated to making the world of board games fun and accessible for everyone.

Their events are always changing and you can see what they have coming up at www.playboardgameempire.com. Oh, and if your date doesn’t work out, try attending one of their board game speed dating nights to find your next playing partner.”

Board Game Speed Dating

“And for you board game lovers out there, we’ve got the perfect event for you: Board Game Speed Dating. Each round you play a different board game with a different group of singles. Your host teaches you the rules, then gives you 15-20 minutes to play.

Each game is fun, easy-to-learn and something specifically chosen because it lends itself to getting to know the others at your table. Even if you don’t find love, you’ll still get to play board games all night, so what could be bad about that?”

– Recommendation by Jonathan Krieger, Emperor of BoardGame Empire

Boston Date Ideas for Couples

Redsox Game @ Fenway

Nothing beats a night out with your significant other watching the Sox pound the Yanks. Fenway Park is one of the most historic (if not the most) baseball stadiums in the MLB.

-Recommendation by the emlovz team (those of us who’ve enjoyed a few games ourselves)

Conclusion

So, you’re obviously a hotshot if you’ve made it this far. However, the third date isn’t just about finding an epic dinner location to wine and dine her. A third date is ultimately meant to carry you into a more secure courting phase with the woman in question.

Hopefully, if there was a solid intellectual match and you share some of the same morals and values, then you were both enthusiastic about connecting more deeply.

The goal of the third date is to ensure that you connect on a cognitive level as well as a jiving on a morals and values level. If all of these are present, then the final goal of a third date is to become physically intimate.

If you’ve been MegaDating for a while, you’ll realize that few women arrive at the coveted third date. Likely you’ve been filtering out those who don’t quite make the cut, and with good reason. You’re looking for a woman who you will be excited to wake up next to for years to come.

If you’ve been striking out at any point in your dating funnel, I’m here to help. Book a session with me here to see if we’re a fit and I can explain more about what I do and how I can help you find your own perfect partner.