46 Exciting Second Date Ideas That Will Deepen the Connection

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Now that you’ve got that butterfly-inducing first date out of the way, it’s time to get creative with fun second date ideas and do something that promises adventure and great conversation for the both of you.

I usually recommend that you keep first dates short and simple, like meeting for a quick drink at a bar—that way, if the chemistry just isn’t there, you can call it a night instead of having to patiently wait for your date to chow down his three-course dinner. But now that you know you like this guy and want to see him again, there’s plenty of room to play.

Maybe he suggested where to meet on your first date, and now you want to surprise him by taking him on an unforgettable date he’ll fondly remember for years to come. Dinner and a movie have been done to death, and besides, you want to show this man that you’re different.

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The great news is, it only takes a little bit of effort and imagination to plan THE second date of all dates. Do it right, and you’ll create an experience that puts you both at ease and helps you get to know each other in ways that just won’t happen in a traditional setting. The small talk should be out the way by now, and this is your golden opportunity to ask some more profound questions and figure out if you like this guy as a person.

In my Little Love Steps, step #4 is all about qualifying your options, going out with guys, and exploring new connections—so make sure you enjoy plenty of second dates with guys who interest you.

Are you ready for some of the BEST second date ideas of all time?

46 awesome second date ideas to try this week

1. Go to your actual favorite bar

Here’s some sage advice I want you to remember: NEVER take a man on a first date to your favorite bar. If it ends up being a disaster, that place will be tarnished for you for months. Just don’t do it.

Wanna know when you should introduce a guy to your favorite bar?

The second date.

By this point, you already have an idea of who this man is. You know you’re interested in him; otherwise, you wouldn’t bother seeing him again. You’re now ready to take him to a place where you feel comfortable and to let him see you in an atmosphere that lights you up.

2. Go to an amusement park

Ride the teacups together, explore the haunted house, shoot hoops for prizes, and sip on hot chocolates and pillow-pink candy floss. If you get scared at any point, you’ve got a great excuse to get a little cozier. Plus, the atmosphere at a good amusement park is always buzzing.

3. Volunteer together

If you’re both generous people who enjoy giving back, then one of the best (and most low-key) second date ideas is to go volunteer somewhere together. Hand out sleeping bags and care packages to the homeless. Work a dinner shift at a soup kitchen. Go to an animal shelter and help out.

4. Take a pottery class

Demi Moore and Patrick Swayze made it sexy in Ghost and now is the perfect chance to recreate that infamous scene. It’s always fun to try something you’ve never done before—one of you may even end up discovering a deep love for making pottery!

5. Visit a beautiful garden

Botanical gardens and country parks are beautiful places to casually stroll around, inhale some fresh air, soak up nature’s beauty, and talk freely without worrying about anyone overhearing your conversation. Bring a cup of coffee with you if you need a little energy boost.

6. Grab a lazy brunch

You know what’s less stuffy than dinner?


But you know what’s fancier than breakfast?


You can relax, sip on mimosas, munch on freshly-baked croissants.

The best part is you won’t be worrying about the date until the evening, AND you’ll have the rest of your day to enjoy after brunch is over!

7. Go to a gig or music festival

Next up on my list of second date ideas is to watch a band you like or head to an outdoor music festival for the day. This is perfect if there’s a particular band or style of music you both love. You can share snacks, grab some ciders, dance, sing, and have an unforgettable night.

8. Watch a sports game

Neither of you has to be big sports buffs, but heading to a live game can be an entertaining second date idea. The atmosphere will be electric, you can chat in between tense match moments, and you’ll show him a different side to you that he might not have expected. From football to basketball to ice hockey to tennis—there’s bound to be something you can both enjoy together.

9. Head to a comedy show

The comedy will put you at ease, help break the ice, and is guaranteed to get you laughing together. Plus, when you’re smiling and laughing, you’re instantly more approachable and attractive to men.

10. Walk your dogs (or somebody else’s)

couple walking a dog

If you found out that you both have dogs on your first date, then why not arrange to walk them together for your second date? And if you don’t have dogs but love them, borrow someone else’s dog for the day!

This will give you plenty to talk about and bond over and take the pressure off the conversation.

11. Be a tourist in your city

Most people live in a place for years but still haven’t explored it to the max. So next up on my list of second date ideas is to be a tourist in your local town or city for the day.

Head to a popular attraction, a museum or art gallery, or a historic building. Take a scenic walk through the city, or better still, go without a route mapped out and allow yourself to be surprised.

12. Climb a rock wall

If you both like physical activity and working up a sweat, an indoor (or outdoor) rock climbing session could be the perfect date. And if you’re competitive, you can race each other to the top—loser springs for drinks after!

13. Visit a flea market together

Even if you’re not massively into thrift or antique hunting, perusing flea markets can be loads of fun on a lazy weekend morning. You could even turn it into a game where you set a small budget, and each buy something you think the other would like.

14. Go to a carnival

best ideas for a second date

The carnival isn’t always in town, but if it happens to be right now, take advantage of it. Take a ride in the big wheel, snack on some funnel cake, and enjoy being big kids for the night.

15. Have an evening swim

If you live near an outdoor pool, a swimmable lake, or even the ocean, taking a dip together in the evening can be incredibly romantic and one of the more intimate second date ideas on this list. Just make sure there aren’t any storms coming, that the area is well-lit and not secluded in any way.

16. Take an art class

Painting has recently become a popular activity for date nights, but there’s a twist: you bring your own booze along with you. Even if you don’t have an artistic bone in your body, this date is guaranteed to get you laughing and bonding before you know it.

17. Attend a talk (about anything)

Think about some of the shared interests you uncovered on your first date, and use this to help you select a talk to attend for your second date. It can be on absolutely anything. You’ll get to learn something new, maybe meet some new people, and have plenty to discuss afterward over a drink.

18. Watch the sunset (or sunrise)

date at the beach

One of the most beautiful second date ideas is simply getting outside and letting nature work her magic. If you’re both early birds, then find a romantic place to watch the sunrise together, and if you’re not, then opt for sunset instead. Make sure you pick a clear, cloudless day!

19. Go dancing

It doesn’t matter if you think you’re a TERRIBLE dancer—taking a dance class together is a wonderful way to try and correct those two left feet and have fun learning together. Plus, dancing is sexy.

20. Visit a gallery

There are always new events and exhibitions taking place in galleries, and often there are drinks and snacks included in the ticket price, making it a ready-made date. The art in the background will help spark conversation and give you something to connect over.

21. Take a boat ride

If you live near the water, then it’s time to make the most of it! Rent a small sailboat or yacht for the day, hop on a ferry, or book a fancy dinner cruise. This is up there when it comes to romantic second date ideas.

22. Get an adrenaline hit

Are you both adrenaline junkies?

Why not go skydiving (indoors or outdoors) or bungee jumping, take a ride in a hot air balloon, or hop on a terrifying roller coaster. If you want to take things down a notch, you could always book a ziplining day out.

23. Try a nostalgic activity

Everyone loves a bit of nostalgia, don’t they?

Pick something super old school that encourages you both to reminisce and share about your childhoods. You could play board games in the park, head to an arcade, or even go for a game of laser tag!

24. Do a color run

A color run is an outdoor race with a twist. Everyone gets given a set of brightly colored paints, and everyone begins the race dressed in all white.

The aim of the game?

Throw color EVERYWHERE.

You’ll get some fresh air, a bit of exercise, and have a ton of fun painting yourself a rainbow in the process.

25. Go ice skating

Ice skating is another fun activity to try together, especially if you both know how to skate (ish). During the winter months, ice rinks often pop up outdoors along with mulled wine stands, making it an extra special and cozy date.

And if you don’t know how to skate, you can always hold one of those penguins around the rink to keep you upright!

26. Have an appetizer crawl

cute second date ideas

This is just like a bar crawl, except you swap the copious drinks for small bites instead. It’s bundles more fun than picking one place for dinner because you get to try out lots of different restaurants and cuisines and explore the city at the same time. This one’s a must for all you foodies out there.

27. Go bowling

When was the last time you went bowling? Nobody really cares about how well you can bowl anyway! Grab a few drinks and some slices of pizza and enjoy the night.

P.S if you’re the gutter-ball QUEEN, set up the alley guards on the side and forget about it.

28. Plan a beach date

When it’s nice out, everyone loves a day at the beach. So if you’re lucky enough to live near the seaside, take advantage of it. Get some friends involved, or keep it just the two of you. Pack a picnic, have a barbeque, go for a stroll, or hop on a jet ski together.

29. Go wine tasting at a vineyard

Looking for a more creative way to share a drink? Find a vineyard nearby that offers wine tasting evenings! Learn some fun facts about grapes, try some delicious wine (and maybe some cheese, too) and get cultured simultaneously.

30. Head to a karaoke bar

If you’re the kind of person who’s up for getting up on stage in front of a room of strangers and belting out a song, take your date to a karaoke bar. There’s a lot to learn from someone’s go-to karaoke song.

31. Grab a food truck dinner

Food trucks can be found all over the place, and they promise delicious, more-ish snacks and treats that you often can’t find anywhere else. Here’s how to make it more interesting: order food for each other!

32. Go to the farmer’s market

The farmer’s market can be a treasure trove of delights like local fresh produce, beautiful flowers, and bites to eat. Maybe you could pick out ingredients to cook dinner together or just grab a coffee and sample some of the food from the various sellers.

33. Attend a poetry reading

If you’re both into literature and arts, then a poetry slam might be up your street. You can never know what to expect: sometimes it’s terrible, other times it’s spectacular. Have a backup plan in case you need to bolt halfway through.

34. Go rollerblading

awesome second date ideas

Rollerblade your way across the city together and enjoy seeing the sights in a new and unexpected way! There’s always the option of heading to an 80s-style roller disco too.

35. Split an ice cream sundae

Head to a dessert parlor and split the biggest ice cream sundae you can find. You’ll feel like you’re ten years old again eating far too much ice cream—the best part is there are no parents around telling you not to.

36. Visit your favorite bookstore

This is one of the more understated second date ideas, but it’s perfect if you’re both avid readers. And in case you didn’t know, bookstores are romantic as hell. Pick your favorite one, grab some coffee, browse the shelves together, and find a quiet spot to chat. You could even pick out your favorite book for each other as a gift.

37. Go fruit picking

Depending on the season, picking fruit (or vegetables) is a wonderful way to spend a date outdoors and sample all the delicious produce. Head to an apple orchard, a strawberry field, or even a pumpkin patch. If you want to extend the date, take what you pick home with you and cook something delicious with it together.

38. Enjoy an adventurous meal

The best way to spice up a plain old dinner date is to get out of your comfort zone. Try a cuisine you’ve never tried before. Order something off the menu you would never usually dream of ordering. Who knows… you might just end up discovering a new favorite.

39. Go for a hike

A hike can be a fantastic way to spend a second date if you both enjoy being outdoors. Pick a scenic trail, pack a hamper of goodies, and enjoy each other’s company.

40. Shoot pool

I have to say, there’s something sexy about a woman shooting pool, even if she doesn’t know how to play. If this sounds like your jam, find your nearest dive bar, grab some beers, and enjoy! Mix it up with a game of darts or even foosball.

41. Go kayaking

Kayaking is a brilliant way to test how well you work as a team because if you don’t, you’re at risk of capsizing! Remember, if you do fall into the water, laugh it off and get back in there.

42. Have a bonfire night

This is perfect for a group date. Invite your favorite people over, load up on drinks and food, and set up a cozy bonfire in your backyard or at the beach. If someone has a guitar (and can play it), make sure they get an invite too!

43. Go for a bike ride

couple riding bikes

Many cities now have bikes dotted all over that you can rent for the day and pick up and leave at various stops. Biking is a brilliant way to see the city better and explore streets and corners you’ve never ventured down. And if the thought of biking in the city is intimidating, find a quieter, off-road trail instead.

44. Play a game of mini-golf

Mini-golf is one of those cute second date ideas that never gets old. There’ll be plenty of banter, you can share cocktails, and you can gauge how competitive you both are.

45. Get your fortunes read

Whether you love going to fortune-tellers and psychics or you’re a little bit skeptical, this can be another fun way to connect. Plus, it’s a great way to see how open your date is to the mystical stuff.

46. Take a picnic to the park

Packing a picnic is a classic date idea but what makes it so great is that you can enjoy some amazing food and drink in a casual yet intimate setting. Splurge on a bottle of bubbly, pack some gourmet sandwiches and nibbles, and a soft blanket.

Ready to go on some unforgettable second dates?

You’ll never wonder, “what should I do on a second date?” again.

I hope this list has shown you that second dates should be enjoyable and help you build on the connection you’ve already made. This is your opportunity to get creative, offer a unique side of yourself, and share a memorable experience with someone. Even if things don’t go anywhere with this guy, the least you want to do is have an amazing time on this date.

Have you got any fun second date ideas that aren’t on this list? Tell me about your favorite second date go-to’s in the comments below.

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2 years ago

Great ideas!

2 years ago

you forgot ho to church together be realistic those who pray together stay together

2 years ago

So the woman initiates the 2nd date?

2 years ago

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Last edited 2 years ago by annagrey
2 years ago


2 years ago

Some nice ideas but not very practical for a 70 + yr old woman and her 66 yr. old friend who live an hr. apart. He works full time, and has a private practice, so earliest dates are early evening, not morning. Love the vineyard idea, but way too far away. Please keep those ideas coming. Don’t want us to get bored.

Robert Ingram
10 seconds ago

I especially like the idea of visiting a botanical garden or seeing a comedy geometry dash online, as these are activities that you can both enjoy and talk about.

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