29 Fun Second Date Ideas That Are Anything but Awkward

From wine tasting to painting class

second date ideas man and woman walking at a vineyard
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Dating is fun...when it goes well. But a bad date can feel like such an awkward flop that you end up wondering if you should resign yourself to the single life forever. So, if you’ve scored a second date with someone you dig, set yourself up for success by planning a date that does you both right, and keeps things moving in the right direction. What should you do together, dinner and a movie? Nah. You can do better than that. Instead, try one of these 29 creative second date ideas for a fun and memorable night with your future soulmate.


second-date-ideas: couple bowling
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1. Go Bowling

Get your Big Lebowski on, and let the good times roll with a fun and casual activity that’s impossible not to enjoy. Add some goofy shoes, a couple beers and a side of fries into the mix for a combination that’s sure to make any pair feel footloose and extra-friendly. Bonus: If you aren’t particularly skilled at bowling, this one is also a reliable way to make your date laugh.

2. Visit a Rooftop Bar

Stunning, panoramic views and booze. Need we say more? Grab a drink with your love interest at a swanky rooftop establishment for the ultimate anti-dive bar experience (i.e., fancy cocktails and fresh air). Trust us, you’ll both be on cloud nine and ready for another round...maybe even date three?

3. Go for a Hike

Olivia Newton John was definitely onto something: Get physical on your second date with a good hike and you’ll both be singing the praises of exercise and, perhaps, one another. Bonus points if you pick a trail that ends with a scenic view—in the hiking world, they call that a climax.

second date ideas: couple Cooking Dinner Together
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4. Cook Dinner Together

An intimate meal out is great, but let’s be honest, if it’s only a second date, there’s a sizable risk that the small talk will be stilted and awkward. Spare yourself this uncomfortable situation by dining in, instead. Cooking a meal with a potential love interest is a surefire way to break the ice before dinner—you know, so you can get to know each other with conversation that actually feels natural.

5. Take a Beach Day

So you like long walks on the beach. OK, just kidding, that one is so cliché it’s an instant dating profile pass—but that doesn’t mean there’s something wrong with the beach. Suit up and go for a swim with your future sweetheart, or just lay down a couple towels and get to know each other better.

second date ideas couple having a picnic
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6. Picnic in the Park

If the weather is good, get ye to the nearest public park for your second date—just make sure one person is responsible for bringing a gourmet spread. A blanket, a little baguette with brie, fresh fruit, fresh air—all you need for a relaxing rendezvous that will feel just right. Bon appetit.

7. Go to a Drive-In Movie

The drive-in is a throwback viewing experience that has (thankfully) survived the test of time. Best of all, it is infinitely more fun than Netflix and chill. Bring snacks and refreshments—non-alcoholic only, of course—and enjoy a good flick from the comfort and intimacy of your car, where chatting and PDA won’t break any rules, or disrupt anyone else’s date.

second date ideas playing cards
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8. Play Cards

Believe it or not, you can learn a lot about someone by playing a card game with them—like where they fall on the sportsmanship spectrum, for example. Plus, a little friendly competition will bring both entertainment and excitement to the table.

9. Go Wine Tasting

Tasting: The only time you can sip from five different bottles of wine in one sitting and feel good about. Try it out with your love interest for an intimate date—you’ll benefit from the romance of learning something new together and you might discover you both have the same taste in vino, too.

10. See a Comedy Show

Banish second date butterflies with the ultimate tension-reliever: Humor. Comedy shows are a great way to share some irreverent laughs together and break the ice. You’ll also get to see just how easy-going your date is should a ruthless comic decide to do some crowd work.

second date ideas Go on a Boat Ride
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11. Go on a Boat Ride

Charter a boat or take a ferry ride together for a relaxing, energizing and romantic date. For conversation and atmosphere, a private sailboat is a bonus, but even a diesel-powered commuter ferry has its charm as long as you can snag a spot by the rail for a better view. (Hint: Go for a boat with a bar on board.)

12. Bocce Bar Date

Find a bar near you with a bocce ball court and get your game face on. Bocce, also known as Italian lawn bowling, is a super fun outdoor game that goes well with a frosty brew and good company.

13. Take a Workout Class Together

If you’re both gym rats, do what you love together. Whether it’s yoga, an outdoor HIIT class or your own at-home routine, breaking a sweat together can also help break the ice.

second date ideas: People picking up garbage to clean a public park
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14. Volunteer Together

If activism and showing up are important to you, give your date the chance to show you if they’re on the same page. Pack lunches for your local mutual aid group. Donate some hardcovers to a local book fair. Spend time at a dog shelter. There are endless ways to do good. Who knows? Maybe you’ll wind up adopting a lovable pup down the road.

15. Take a Painting Class

What’s a better way to get to know each other than showing your potential boo that you’re artistically gifted? Find a sip and paint location near you and show off that creative prowess. The best part is, most sip and paint venues allow you to bring your own bottle of wine, so at least you’ll score some easy giggles if it turns out you’re not the second coming of Frida Kahlo.

second date ideas sunset
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16. Watch the Sunset

Busy careers and the lingering pandemic can make setting a reservation tough. So, if you simply can’t wait to see your suitor, plan a little date where you two can just watch the sunset. Bring some small bites and a bottle of wine to just unwind.

17. Hit up a Karaoke Bar

This is the easiest, most fun way to see if your musical tastes align. Will they singalong to pop favorites like “A Thousand Miles” with just as much enthusiasm? Or are they more into slow and steady R&B?

18. Have a Dessert Date

Instead of meeting up for an entire meal, why not just cut to the best course—dessert? Head to a cute dessert bar like Spot Dessert Bar in NYC, for example, where you can select decadent Vietnamese and Thai-inspired desserts. Trust us, everything is better with a warm dark chocolate cake filled with matcha ganache and served with matcha green tea ice cream on the side.

second date ideas Go on a Bike Ride
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19. Go on a Bike Ride

Rent some bikes and take time to not only get to know each other more, but also explore new places in your city. Find a scenic park, beach or biking trail where you can pull over, admire the view at the end or even set up a picnic.

20. Watch a TV Show Together

If neither of you has watched a wildly popular show—Virgin River, Killing Eve, Bridgerton, etc. —there are tons of options to stream an episode or two of on your second date. If you both hate it, then you can pick it apart together. And if you end up loving it, well, then you have a potential story for the grandkids, no?

21. Head to the Library

If both of you are book worms, consider spending the day perusing the romantic words of some of the best poets that ever lived. Start with some of William Shakespeare’s famous sonnets, then work your way to the swoon-worthy prose of Pablo Neruda and Emily Dickinson.

22. Go Stargazing

Grab a cozy blanket, head to your rooftop or park where you can lie down and cuddle under the shining stars. Telescope optional.

second date ideas: Rear view of couple with arms raised about to begin descent on roller coaster in amusement park.
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23. Go to an Amusement Park

Think about it, you don’t have to worry about a lull in conversation when you’re busy jumping between roller coasters, bumper cars and arcade games. Make the date extra sweet by winning each other prizes and sharing a cotton candy.

24. Make a Collaborative Playlist

Research shows that music helps synchronize our bodies and brains, and has an impact on the neurochemicals responsible for feelings of closeness and connection. Capitalize on this by planning an at-home date that involves little more than sharing music (over a bottle of wine, perhaps) and working together to build a soundtrack for your budding romance.

25. Visit a Sculpture Garden

Museums are great, but the vibe can be a tad stuffy. Sculpture gardens, on the other hand, are an ideal place to soak up some culture while also getting some fresh air and sunshine. (Psst: If the park permits, we strongly suggest packing a picnic so you can enjoy the artistic landscape and a romantic lunch for two.)

second date ideas man and woman at an art gallery
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26. Go Gallery Hopping

Gallery hopping has a lot going for it—like the fact that you’ll be surrounded by conversation starters. Plus, admission is always free and sometimes the wine is, too.

27. Plan a Bar Crawl

There's no need to put the pressure on one person about where to meet when you know you'll be hitting up a few different spots. Each of you can choose a couple of your favorite places, then alternate whose pick you stop by for a drink.

second date ideas couple in new york city
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28. Play Tourists in Your Own City or Town

You don’t have to travel far to feel like an out-of-towner. In fact, if you’ve been living in the same place for a while, there’s a good chance you haven’t thought to explore (or revisit) many of the popular tourist destinations on offer.

29. Go Thrifting

Grab your new boo and head to the nearest antique shop, flea market or thrift store to see if you can scout out something truly special. Even if you return home empty-handed (unlikely), you’ll still have benefited from the shared mission and time spent together.

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