Having a rough time figuring out what to do for your Valentine’s date? Let’s fix that!

Pick any number between 1 and 20. Got it? Good. Look below to see your Valentine’s Day date idea and soundtrack song.
Have fun, lovers!

  • #1 - A Swift Romantic Walk

    YOUR DATE: Take a romantic walk through the Boston Public Garden and Boston Common.
    YOUR SOUNDTRACK: “Love Story” by Taylor Swift

  • #2 - Bad Art & Broken Roads

    YOUR DATE: Go to the Museum of Bad Art in Somerville then go home and make horrible paintings for each other.
    YOUR SOUNDTRACK: “Bless the Broken Road” by Rascal Flatts

  • #3 - A Righteous Sunset

    YOUR DATE: Head to the coast and watch the sunset at one of Massachusetts’ many beautiful beaches.
    YOUR SOUNDTRACK: “Unchained Melody” by The Righteous Brothers

  • #4 - Mysterious Echo Bridge Date

    YOUR DATE: Go to Echo Bridge in Newton, each stand on one end, and yell “I LOVE YOU” at each other like maniacs. Due to the unique architecture of the structure, sounds produced under the bridge can echo up to 25 times.
    YOUR SOUNDTRACK: “The House That Built Me” by Miranda Lambert

  • #5 - Go Get Froggie!

    YOUR DATE: Go ice skating at the Frog Pond on the Boston Common.
    YOUR SOUNDTRACK: “From the Ground Up” by Dan + Shay

  • #6 - Creepy Trains and the Sinking Boat Song

    YOUR DATE: Go to Martini Junction in Needham and experience the creepy and ellaborate toy train set set up in the middle of nowhere. Bring a picnic and have the creepiest romantic picnic ever.
    YOUR SOUNDTRACK: “My Heart Will Go On” by Celine Dion

  • #7 - Amazing Mountain Views

    YOUR DATE: Take a scenic drive to the Berkshires and enjoy the winter scenery.
    YOUR SOUNDTRACK: “Amazed” by Lonestar

  • #8 - Wanted: Beer Tasting

    YOUR DATE: Head to the Berkshires for some craft beer tasting (and delish food munching) at Barrington Brewery & Restaurant in Great Barrington.
    YOUR SOUNDTRACK: “Wanted” by Hunter Hayes

  • #9 - Plymouth ROCK!

    YOUR DATE: Take a day trip to one of Massachusetts’ historic towns, like Plymouth.
    YOUR SOUNDTRACK: “For Those About To Rock” AC/DC

  • #10 - Most Romantic Date Ever... and Saugus Wings.

    YOUR DATE: Cute couples pic (err… THREESOME pic?!?) with the famous Orange Dinosaur on Route 1 in Saugus then a pupu for two and scorpion bowls at Kowloon.
    YOUR SOUNDTRACK: “I Will Always Love You” by Whitney Houston

  • #11 - Classic.

    YOUR DATE: Enjoy a cozy night at home with a candlelit dinner and a movie.
    YOUR SOUNDTRACK: “God Gave Me You” by Blake Shelton

  • #12 - Zippin' With Old Blue Eyes

    YOUR DATE: Couples ziplining through the trees at Boundless Adventures in Berlin.
    YOUR SOUNDTRACK: “The Way You Look Tonight” by Frank Sinatra

  • #13 - In this case the A stands for Arancini

    YOUR DATE: The North End of Boston! Just go hungry and have a blast!
    YOUR SOUNDTRACK: “What If I Never Get Over You” by Lady A

  • #14 - "Yours" is NOT a Cheesy One!!

    YOUR DATE: Go to a karaoke bar and sing cheesy love songs to each other.
    YOUR SOUNDTRACK: “Yours” by Russell Dickerson

  • #15 - Distinguished Dunkin' Date

    YOUR DATE: Pretend you’re Jennifer Lopez and Ben Affleck and walk into Dunkin’ like you’re superstars… then have your Valentine’s Date there. Bonus points if they let you run the drive through for a minute ala Ben.
    YOUR SOUNDTRACK: “At Last” by Etta James

  • #16 - Don't You Just Love...

    YOUR DATE: Bargain huntin’ at Christmas Tree Shops! While there buy each other the gaudiest Valentine’s Day gift you can find in the store. Surprise! Don’t you just love a bargain?
    YOUR SOUNDTRACK: “My Girl” by Dylan Scott

  • #17 - Easy Money!

    YOUR DATE: High rollin’ at Encore Boston. Dinner at Rare Steakhouse if you do well. McDonalds on the way home if you don’t.
    YOUR SOUNDTRACK: “You Make It Easy” by Jason Aldean

  • #18 - Banana Fluffernutters?

    YOUR DATE: Fluffernutters wherever.
    YOUR SOUNDTRACK: “Can’t Help Falling In Love” by Elvis Presley

  • #19 - Diabolical Date

    YOUR DATE: Isabella Stewart Gardner Museum in Longwood. The museum was home to the greatest art heist in history, so seeing the empty frames is unusual but interesting.
    YOUR SOUNDTRACK: “Better Together” by Luke Combs.

  • #20 - Cigs at Ziggs

    YOUR DATE: Split a sub or two at Ziggy’s in Worcester. If you’re smokers, experience a butt outside together. (It’s already local legend.) If not, good on you.
    YOUR SOUNDTRACK: “Enter Sandman” by Metallica

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