10 Fun Things to Do on a Date, According to You, Our Readers


The dating game has changed quite drastically over the past few decades, but one thing that remains the same is the desire to come up with inventive and exciting plans whether you’re out with a new special someone or with your trusted partner. It can be difficult to continuously drum up ideas that are a bit more original than the tried-and-true dinner and a movie or an after-work cocktail.

To get inspired, we asked you, our readers, to share with us your best dates ever. From helicopter rides and concerts to hometown dates and vineyard visits, your most cherished memories are seriously motivating. If your love life needs a little spicing up, take a page from the dating handbooks of these real women who’ve been on some pretty spectacular dates—though it’s not always the showiest plans that create lasting impressions. If you’re looking for fun things to do on a date, inspiration awaits.

Enjoy a Concert

The most fun I’ve ever had on a date was when I was still in college and agreed to go to a piano violin concert with a Juilliard concert piano student. Classical music becomes a lot more exciting when the person next to you knows all the intricacies.

Audio Pro T3 Speaker
Pottery Barn Audio Pro T3 Speaker $249

Go Wine Tasting

Road trip to his family’s vineyard where we got to trim the vines, had a private tasting, and had a wonderful dinner with the new friends we made!

Metropolitan Wine Glass, Set of 2
Vera Wang Metropolitan Wine Glass, Set of 2 $50

Get a Little Competitive

Playing spontaneous basketball.

Glass Water Bottle
BKR Glass Water Bottle $35

Do a Seasonal Activity

Going bobsledding in Lake Placid over New Year’s, screaming in my boyfriend’s ear the whole way down, but loving every second of it.

Solid Basketweave Throw
West Elm Solid Basketweave Throw $79 $59

Explore a City

My husband (then boyfriend) took me on a tour of downtown L.A. We went to Grand Central Market, Angels Flight, MOCA, The Bradbury Building, and ended with drinks at The Perch and watched the sunset. His late stepdad took his mom on the same first date. I thought it was so thoughtful and romantic.

Laurel Moglen and Julia Posey 111 Places in Los Angeles That You Must Not Miss $14

Find a Festival

A concert and beer festival! It was a perfect evening.

Beer Tasting Set
Crate and Barrel Beer Tasting Set $30

Go Big, or Stay Home

We flew to L.A. and saw Hamilton. That or eating spaghetti and drinking champagne on the floor of my empty apartment on NYE.

Elegance Champagne Coupe, Set of 2
Waterford Elegance Champagne Coupe, Set of 2 $60

Wander Through a Museum

I had just moved to London, and my guy friend (now my boyfriend of three years) told me we were going somewhere, but I had to guess. I had no idea the layout of the city, and it took us 45 minutes, but he surprised me with the Tate Modern. We walked around and stared/misunderstood art and laughed a lot.

Susie Hodge How to Look at Art $14

Go on a Hometown Date

Going to Queens with him because it’s his hometown!

Seasonal Weekend Bag Luggage
Lipault Seasonal Weekend Bag Luggage $99

Take Flight

When my husband recently surprised me with a helicopter ride back home to Philly from our amazing day celebrating our 6th wedding anniversary in NYC.

Aviator Sunglasses
Ray-Ban Aviator Sunglasses $145

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