19 Creative Date Ideas To Try, Whether It's Your First Date Or 100th

Dates don't have to be just drinks and dinner.

Create And Fun Date Ideas For All Relationships & Love Stages Unsplash

By Lisa Holden

The new year is the perfect time to rethink your tried-and-true dating habits. So, how about this year, you try a more creative date night (or day) idea?

RELATED: 13 Cheap, Yet Fun & Romantic Date Night Ideas You've Probably Never Thought Of Before


The go-to options are dinner and drinks, but let's think outside the box on some fun ways to spice up your love life in 2019.

1. Mini Golf

This is so low-pressure, it's great for a first date (or fifth, or a fiftieth). When you're on a date, you don't want the stakes so high that either party looks bad if they don't have the training necessary to complete the task (think tennis or skiing), but not so low that there's no room for a little flirtatious competition.

Since a mini-golf course is usually built for kids, it's going to be simple enough to complete, but gives you something more to do than exchange questions over drinks. If it's the first date, leave it at mini golf, since you don't want a first meeting to last longer than a couple of hours anyway. If it's further in, go to dinner or drinks after the golf, and make sure to set a fun, flirtatious bet before you begin!


2. Wine Tasting

It's not just going to drinks. Wine tasting is far more exciting than wine drinking. Here's why: nobody knows that much about wine. Sure, there are professionals out there who actually know what they're talking about, but for the most part, going wine tasting is fun because you learn more about terms like "varietal" and "tannins" that make you sound fancy and cultured.

If you actually know about wine, great: this is your opportunity to show off and make your date feel awesome for being with a wine badass. If you don't, here's what you do: every wine you try, think about what food you'd want to eat it with.

Don't worry if food isn't your thing either; there are no wrong answers here, and sometimes the worst answers are the most entertaining. For example, I was once on a date at a winery and I said the pinot would go nicely with spicy cheetos. Not only did the pourer bowl over laughing, but my date found it charming and hilarious. You, too, can be the spicy cheetos girl at the next fancy winery. Dream big.

3. Walk on the Beach

This makes an excellent date because it can be as long or as short as needed. If it's a first date, don't make it too far, strenuous, or secluded, and make sure you time it right so that you're hitting the sunset toward the end of the walk, not the beginning. A nighttime beach walk gets creepy quickly.

However, if it's not a first date, a nighttime beach walk is sexy as hell, and as long as the mutual attraction is there, you will definitely make out in the moonlight. It's nearly foolproof.


4. Ask Each Other the 36 Questions

In 1997, a group of social scientists shared a practical methodology outlining how they successfully created human closeness in a lab setting. In 2015, Mandy Len Catron published a personal experiment with the methodology in the New York Times titled, "To Fall in Love With Anyone, Do This." Then, my brain and everyone else's exploded when we realized all we had to do to fall in love was ask each other these 36 questions.

This is way too intense for a first date, but a couple dates in, throw this out as an idea and see if your love interest has heard of it. I'll warn you that I tried this with someone I'll call "work flirt," and things got too real too fast and we had to put the kibosh on the whole thing.

5. Pub Trivia

First dates should be fun, easy, low pressure, and no more than an hour's time requirement. For those reasons, keep trivia in your back pocket until at the very soonest, the third date. If you have an existing trivia group, don't just show up with a date. Find a new trivia spot to try with just your new honey and wait until things are a little more established until you throw them to your group trivia environment with all your friends.

On the flip side, trivia is a great place to turn a friend into a romantic prospect because people usually go in groups and it's the kind of low-pressure environment someone can bring a co-worker or friend who's new in town. This actually worked in my favor once when my girlfriend's buddy from church brought his very handsome and newly single roommate. I flirted my ass off and we ended up dating for a few months. I still praise trivia for meeting that killer cutie and love going to this with my friends.


RELATED: 7 Cheap, Cozy Fall Date Ideas For Couples

6. Sailing

This was maybe the best date I've ever had. I matched with a sailor on Hinge who talked up his boat and how much he liked Champagne. So much in common already: I love wine, including the bubbly kind, and people who have boats. He offered to sail me around the San Francisco Bay, and while I can't wholeheartedly endorse this as a first-date activity because of the obvious and inherent danger, I threw the rule book out and said yes anyway.

I'm here to tell you it was epic. He taught me how to "tack," which is a sailing term meaning do exactly what the captain says and retain none of the information after the experience. He also taught me words like "port" and "starboard" and let me steer.

If you're even a little bit clever with words, sailing is a flirtation environment goldmine. Everything is flirty including calling the other person captain, talking about safety, tying knots, I could go on. I realize this could have gone horribly wrong and does not meet my criteria for a first date only lasting an hour or giving yourself an easy exit, but sometimes ya break the rules and up with a great date story.


7. Watch the Sunset

Like most of my demographic, I'm a sucker for a pink sky. Hand me a glass of Sauvignon Blanc, my iPhone, and a blanket at sunset, and watch while I thrive. This one is so low pressure and friendly, it's a timeless date that can easily be a first. Grab a blanket, snacks, and just find high ground. This gives you plenty of time to chat and get to know one another. but not so much time that you feel stuck there for too long.

I once went on a date that culminated in burritos at sunset and I honestly wondered if I'd marry that guy. He ended up never texting me again, but that's cool, I guess you don't like perfection, studly Canadian man!

8. Escape Room

Okay, these things low-key terrify me, but they make the list because my friends who are smarter than me love them. From what I understand, you sign up to go into a tiny locked room with strangers. You're then handed a list of riddles and puzzles you have to work out in order to escape. The whole thing is timed so there's added pressure, and there's absolutely no room for small talk.

This is the opposite of my thrive zone. However, for the brainy types out there, this seems to be a real aphrodisiac, so I suppose I shouldn't knock it 'til I try it. If you're crushin' on someone with an advanced degree or a knack for puzzles, consider this for a second or third date.


9. Art Class

Think: wine and paint nights, pottery painting, pottery shaping, succulent arrangements, anything. This is fun because they usually only last about 90 minutes, and giving yourself something to do with your hands is a great way to calm your nerves. You also have tons of built-in conversation-starters around whatever it is you're creating. A great non-drinking first date, this is also an excellent third date because it can lead to dinner or a nightcap afterward.

10. Walk a Dog

Don't have a dog? Borrow one. I had a dog for years, and I'm telling you dog owners always welcome someone who is willing to wear their pup out on a nice long walk. Plus, who's saying no to this text? "Hey! I'm watching my friend's dog today, care to join this cutie for an evening stroll? [insert photo of dog]" If your date says no, congratulations, you've eliminated a heartless candidate who doesn't share your interests anyway.

RELATED: 7 Autumn Date Ideas That'll Make You Fall For Him All Over Again

11. Comedy Show

This suggestion comes with a two-drink and a two-date minimum. Don't put a first date through this, but definitely suggest this for a third, once you know their humor and style. Comedy shows are great because you don't actually have to come up with pithy conversation the whole time.


Just sit back, relax, and let someone else be charming for an hour or so. After the show, you'll both be all giggly and adorable so take a walk or grab frozen yogurt and keep the chuckles going.

12. Outdoor Concert

The ultimate Summer date — get cheap lawn seats and bring a blanket that's big enough for two, but small enough that you'll sit close and snuggle. Tread lightly on booking this for a first date, but it's fine for a second. Plenty to do, talk about, and opportunities to get close means this date is often a good closer to see if someone is really into you. Keep the pressure light by meeting at the venue.

If that's not feasible, aim to get your date home safely after the event, but don't try and keep the night going. Concerts are exhausting, so send your date home and embrace the opportunity to leave them wanting more.

13. Cook Together

A cooking class makes a fun date because it's not on you to dazzle for two hours; it's on the instructor. What's more, you can spend time developing a skill with someone that you two can try together at home on a future date. If cooking is your thing, skip the class and simply invite your sweetie over to show off your culinary skills. I only do this when I really like someone because I've realized inviting someone over is incredibly intimate and you have to be ready to shine.


To do this right, complete all the cumbersome things before your date arrives so that you can do the light tasks while engaging in conversation. It's very important to give your date something to do so they're not just sitting there waiting to eat. Things like opening wine, snapping string beans, separating cauliflower florets or tearing lettuce are nice because they're easy tasks that aren't too messy and don't require a lot of equipment. You can set them up doing something like that at your kitchen counter while you work away. I highly recommend treating yourself to a cute apron as well. Trust me, they lose their minds over an apron.

14. Go-Kart Racing

This also falls into the bucket of exciting enough to be competitive, low enough pressure to be fun. Don't overthink this one: just wear some cute athleisure and show up to suit up. Go-kart racing can be as flirty as you make it, and with a helmet on your head and the gas pedal under your foot, you might be invigorated with enough adrenaline to really show your date what you've got.

Just make sure to keep it light, and if you have competitive tendencies, curb them with a bet like "winner buys snacks" or something. If it's a first date, leave it at the racetrack. If it's second or beyond, grab a bite or a beer after, and see if you can lock in that next date for a rematch.


15. Pet Adoption Fair

This one is so good, I'd take myself on this date. Lots of cities have them and it's a great option for a day date when you're just getting to know someone. With the adorable content laid out before you, there's virtually no pressure to be the cutest one there, so all you do is bask in the cuteness all around you. Not ideal for the allergy-prone romantic prospects, but if you've had a bit of banter about animals, consider throwing out this curveball as a first date suggestion. Just make sure you don't come home with joint custody of a gerbil or something.

16. Hike

An opportunity to show off your favorite pair of leggings, a hike also provides great views, great photo ops, and something to physically be doing if the conversation drops at any point. I like a hike as a first date, but just make sure it's feasible to arrive separately, and time it so that things last no more than two hours (and end no later than sunset).

17. A Funky Movie

Ever been to one of those movie theaters with a full bar and gourmet snacks? How about a drive-in? Even an independent film will do: just think outside the box office and throw out a movie idea that involves a little extra flair. Ideal for a second date or beyond, this plan isn't great for getting to know someone but is a fun option when you want to spend time with a new love interest and impress them with your creativity.

18. County Fair

It's in about a million country songs for a reason: it's cute. With plenty to do, lots of walking involved, and all sorts of sights and sounds, there's low pressure on you to make conversation. Just keep in mind, this may last several hours, so only take someone to this if you already know you like them. Don't be cheap about the snacks, either. With cotton candy, corn dogs, and giant pickles everywhere, the food is half the fun, so bring cash and offer to buy your sweetie a favorite treat.


19. The Zoo

Much like the fair, you've got sights, sounds, and walking to keep you busy. I grew up in San Diego, so that world-famous zoo is extra nostalgic for me, but any wildlife sanctuary will do. If your romantic candidate is an animal-lover, this day date is creative enough to be enticing and relaxed enough to make it a no-brainer. If your zoo has a tram ride or gondola, perhaps, save that part for the end. It's a great place to sneak a kiss, or at least a snuggle if you're both feeling it.

RELATED: 26 Fun (But Cheap!) Date Ideas For When You're Trying To Save Money

Lisa Holden lives in San Francisco, California and has been on more than 100 first dates. A branding and communications professional by day, she pulls from this knowledge to help her friends and readers determine how to behave before, during and after a date.