Let's Make Dating Simple

Dating Coaches Executive Matchmaking Virtual Dating Dating Advice Become a Client

10 First Date Ideas for Couples Over 40

So you’ve found someone you think you’ll connect with, and it’s time for that first date. But things are different. Whether you’re dating after divorce in your 40s or dating with kids, you’re not interested in just grabbing coffee or dinner. No, you want that person to see the real you. But what do you suggest? Where do you go? Our dating coaches have taken that burden off your shoulders by putting together a list of first date ideas for couples over 40 to take some of the pressure off and help turn that first date into a second one.

Browse a Bookstore

If you’re not ready to stray too far from the classic coffee date, consider setting up your first date at a cafe attached to a bookstore. Plenty of bookstores now have an area where they sell coffee, and they might also provide cozy seating where you can enjoy your drinks. Before you order, take some time to walk through the stacks and chat about your favorite authors or what you’re currently reading. Check out Brattle Book Shop if you’re in the Boston area. It’s three stories of used books as well as rare first editions.

Sample Local Food Trucks

Take advantage of the weather while it’s gorgeous, and make a first lunch date more whimsical by paying a visit to a food truck. Food trucks provide a quick lunch that can be enjoyed outside. Find a street or square where the trucks tend to congregate and take turns choosing items off the menus of different trucks. You’ll have a great time sampling different foods while getting to know what your date likes. You can find over 30 different food trucks at The Greenway if you live in or around Boston.

Mini Golf

Mini golf isn’t just for vacationing families; it’s a stress-free, low-impact activity that will make you and your date unleash your sillier sides. You might be terrible at it, but that makes it all the more enjoyable—who can get the higher (worse) score? The gentle physical activity will loosen you up, and you’ll find yourselves making easy conversation in between swings. Yelp says that McGolf in Dedham is the best mini golf spot around Boston, you and your date should check it out.

Unleash Your Inner Crafter

Get crafty while creating a great first date memory. Go to a painting class together, or attend a cooking class and emerge with a new specialty dish. The possibilities are endless; pick something that you and your date will enjoy learning and trying out. With locations in Hingham, Dedham, Foxboro, Somerville and Lynnfield, the Muse Paintbar gives you the opportunity to show off your artistic ability while enjoying a glass of wine or two.

Visit a Botanical Garden

Botanical gardens will offer a beautiful backdrop to a lovely conversation as you stroll past flowers and greenery. They’re often a little-known gem within communities, and you’re likely to find it sparsely populated. Get to know your date as you take in exotic plants that you wouldn’t normally see in your area. The Boston Public Garden is one of the oldest botanical gardens in American, making it a bucket list item for many.

Embrace Hilarity at a Comedy Club

Avoid an awkward icebreaker conversation by first taking in a show at a local comedy club. Laughter loosens everybody up, and will put you both in a great mood. You could wind up watching an improv group or a string of stand-up comedians—either way, you’ll be able to talk about how good or bad the shows were, your favorite jokes, and whether or not you’d ever find yourself doing something like that. Try Improv Asylum or Laugh Boston for some good laughs.

Experience Nostalgia at a Barcade

Visit a local barcade—a term coined from the combination of a bar and old-school arcade—to relive the glory days of pinball machines and early video games. Take turns buying tokens for the machines, and challenge each other to see who can get a higher score in certain games like Tetris. Loser buys a drink? A4cade by Area Four is a great spot for a gaming faceoff.

Release Your Competitiveness at Trivia

Play into your competitive side in a different way by setting your first date at a local trivia night. Check out nearby bars or community centers and identify some likely places where you can battle other teams for a prize. You and your date might find that you know some interesting tidbits. Or you might fail miserably—but you’ll bond over your lack of knowledge in categories like “Ariana Grande albums” or “obscure movie terms.” Here are 15 of the best trivia spots in Boston.


Volunteering might not seem like the ideal first date, but the key is to pick an activity that lets you get to know your date while also doing some good in the world. Participate in a beach cleanup or spend some time in an animal shelter. There will be many different opportunities to give back to your community at any time of the year, so take a chance and bond with your date while helping others.

Stroll Through a Farmers Market

A farmers market is an easy weekend morning date, and many communities now host a farmers market, particularly when the weather is good. Check out the various local vendors, snack on some homemade treats, and see who can find a more interesting booth. Don’t forget to check out the produce and flowering plants during the summer! While some of the areas most popular farmers markets reside in Boston, you better take advantage soon while the weather is nice.

Find Your Perfect Date with LunchDates

Maybe you’ve got some great date ideas, but you’re still searching for the right person to join you. That search can be frustrating. Why not let the best matchmakers in Boston make your life easier by finding your perfect match? Give LunchDates a call to find out how our experienced dating coaches can help you find love as a 40+ career-minded man or woman.


Get Started Today

Get started meeting successful Boston singles.

Call us: 617-254-3000

    If you’re tired of swiping and ready to make a real connection, contact us now and we’ll discuss how our Matchmaking and Dating Services can help you meet other successful singles in the Boston area.

    Call us: 617-254-3000

    Or provide some basic info and we’ll start creating your Dating Profile:

    Your Contact Info

    Dating Profile Info

    Providing the following information will allow our matchmakers to start creating your dating profile.


    Upload a Photo of Yourself (optional)

    X - Close