Operation Date Night
I challenged myself to come up with 100 creative date ideas.
Now, it's your turn to put them to action!
HOME TOGETHER DATE IDEAS
1. 📇Set a timer for 2 hours and attempt to create a new business from scratch that can make you at least $50 each.
2. 🖇Buy really cheap crocheting/knitting materials, find a cozy spot, and teach yourselves how to make your favorite animals.
3. 📈Take 1 hour to research and/or create content with the aim of making something that will definitely go viral on reddit. After 1 hour, each of you must publish any of the things you’ve created, and over the next 3 hours, whoever gets the most karma wins.
4. 🤪Create a safe physical play space where you can each explore your inner child. Meditate on what you were like at birth, at 3 years old, at 7 years old, and share your stories of the most salient memories you have from those moments. Take some time to play-act what you were both like around that time, to see if you would have become bestest friends had you met at that age. Maybe you wouldn’t have become friends at age 5, but by the time you’re both pretending to be 10, those versions of yourselves would have gotten on swimmingly.
5. 🙊Practice your reality confirmation skills together. First, wander around until you witness a conflict or some interesting social engagement. Then, take turns sharing your best guess as to the emotional states and motivations of the people involved. If you’ve got a sketch pad available, practice each drawing your own rendition of what happened. Also practice writing it in words. See how your versions of reality differ when transposed into different mediums.
6. 💡Sit down with a pen and paper and try to come up with punny and ridiculous business ideas together.
7. 🎲Dice roll date — each of you writes 6 separate things that correspond to the sides of dice. You then take turns throwing the dice and doing whatever the combination calls for, however absurd. The more creative your interpretation, the better. For instance, if you roll “toxic masculinity” and they roll “fried plantains,” well, …uh,….I’ll leave it to you to decide what to do with that.
8. 👨🏼🎨Grab some colored pencils and paper, queue up a Bob Ross video on Youtube, and teach yourselves how to expertly draw things, like mountains, or human faces.
9. 🔮Agree beforehand on a life skill you both mutually want to learn, then meet up with a singular focus upon helping each other learn that skill, whether through video tutorials, asking friends for help, or wandering to a local venue where you could learn from a professional.
10. 🗣Find a quiet, comfortable place, lay on your backs, and share secrets with one another. Preferably your secrets. Gradually escalate in intensity.
11. 🏋🏽Snag a free trial membership to a fancy gym, and go together for a workout, or sauna, or impromptu squash match.
12. 🦄Pick your favorite fantasy series and create an immersive marathon around it. For something like Lord of the Rings, begin playing the movies while simultaneously reading passages from the books out loud to one another. Obviously dress up as your favorite characters, too, and maintain all proper accents through the duration of your immersive date.
13. 🎯Pick something you both find very annoying, then invent a product or service that would solve that problem. If needed, hit up hardware stores, flea markets, and thrift stores to collect interesting materials for your invention.
14. 🧘🏿Throw an introvert party! No talking allowed. Encourage quiet reading, writing, journaling, stretching, yoga, sound meditation, acupuncture, and other activities that require no direct verbal communication and let you explore your own inner worlds.
15. 🃏Using only pen, paper, and markers, attempt to design your own fully robust board game in under 5 hours.
16. 🎇Create a doomsday prepper kit together. Include some victuals, tools, medicines, and other must-haves. Draw up your escape plans, along with backup plans, a list of your best allies (people who have access to land, medicine, transport, food storage, etc.), and any specific survival skills you’d need to ensure that someone in your party possesses. Which one of you is best prepared for a sudden apocalypse?
17. 📺Pick a series both of you have been meaning to start watching, and commit to binge-watching an entire season of it. As preparation, make an action plan of how you’ll spend your breaks between episodes — consider massage, meditation, snacking on your favorite goodies, exercise, and “exercise”.
VENUE-SPECIFIC DATE IDEAS
18. 🖼Go to an art museum and come up with as many “classical art memes” as possible together, saving them on your phone and posting your favorites on social media.
19. 🎬Find a listserv (or ask your actor/director friends) of any local shows being filmed, and see if you can land a spot together as extras or background characters.
20. 🗒Go to a stationery store to procure a calligraphy pen and paper, then find a quiet place to write letters of gratitude to people you care about. Share stories with one another that capture why you care so much about this person.
21. 👵🏽Schedule a visit to a local retirement home and ask the people there to tell you stories of their proudest / most cherished memories, or of interesting historical events that they happened to witness, and learn how their recollection may differ from what you learned in school.
22. 🎤Go to an open mic night and see if you can both get on the list to perform. Bonus points if you can perform together.
23. 🎮Visit several local arcades and see who can rack up the most high scores across the most games.
24. 🎰Go to a Dave & Busters or other similar adventure/arcade space and see how far you can make it without spending any money, and only using either bartering or smooth talking (“hey, we’re on a first date but we don’t have cash. help!”) to convince people to help you play. Bonus points if you can get larger and larger groups of people to rally around helping you two have the best date ever!
25. 🐒Go to the zoo, or any place where you can watch a variety of animals interact, and take lots of photos. Then, come up with the most creative captions you can for each photo, and go print them out and turn them into a photo book. Bonus points if you can seamlessly link all the captioned photos together into one cohesive storybook. Sell it on Amazon. Become millionaires.
ACTIVE & ADVENTUROUS DATE IDEAS
26. 🎟Before your date, each of you creates a mini booklet of citypass-style experience “tickets” featuring your favorite places/shows/events/eateries/experiences in your city, then when you meet up, exchange booklets and take turns using your tickets.
27. 🏔Find the highest artificial and the highest natural points in your area and take a selfie from the top of each one. If time permits, do the same with the lowest points!
28. 🏃🏾Go on a mapped run together — first, take a screenshot of your town on Google Maps, then decide on a word, phrase, or image you’d like to map onto your town by virtue of the running course you decide upon. Open up a run tracking app like MapMyRun, and set out on your desired course until your full word/image is mapped out. Later, if applicable, use that mapped image to share on social media and see if you can get any fun perks.
29. 💃🏻Sign up for a trampoline exercise class and bounce on ALL OF THE THINGS.
DRUG-FRIENDLY DATE IDEAS
30. 🌿Commit to a 1-month quest to uncover the best marijuana strain to pair with massages, and teach yourselves new massage techniques as you go.
31. 🎥Get high, turn on a movie on mute, then take turns picking out a playlist that best pairs with the movie. If you’re feeling particularly adventurous, try uploading sharing your pairing with friends so they can vote on who created the best one.
32. 🎼Pick a mood you’d each like to convey, then spend a few hours together attempting to come up with the ultimate playlist to capture that mood. If desired, accentuate the experience with cannabis, alcohol, or psychotropics.
33. 🍄Create a custom-tailored psychotropic experience for one another, replete with a fantastic multi-hour playlist, creative light displays, fun tactile sensations, and delightful snacks and drinks for replenishing electrolytes.
OUTDOOR DATE IDEAS
35. 👻Go on a ghost hunting expedition through the Brooklyn paranormal society or some other paranormal meetup near you 👻. Don’t forget your EMF meters, EVP audio recorders, trifield meters, and infrared / nightvision IR lights!
36. ⛵️Find your way onto a boat, even if it’s just a ferry. Changing your mode of transportation creates new conditions for bonding, and all ferries have destinations, so you can plot out where you’d like to get off and what sort of adventures you’d like to do once you get there. For the procrastinators, you can attempt not choosing a destination and simply asking everyone on the ferry where you should get off in order to have the best possible adventure. Crowdsource your wisdom!
37. 👨🏻🔧Become Super Mario Sunshine for a day! Pick a park in your city and see if it’s possible for you to physically pick up / remove all the trash in the entire park. Buy some cheap rubber gloves and a few trash bags, then work together collecting whatever you find. Bonus points for whomever finds the strangest thing(s) over the course of the adventure.
38. 🏡Wake up early and go garage sale-ing or thrifting together. Bonus points for whomever can pick up the most interesting / undervalued item.
39. 🏟Get really cheap (<$20) tickets to a sporting event and concoct various forms of “spotting” / scavenger hunt games, e.g. “how many couples can you spot making out.”
40. 🐀Create a scavenger hunt based on things unique to your city, then set out to complete it. Noteworthy NYC examples include “discover 10 rats,” “find 9 people with dope hair / tattoos,” “witness 8 catcalls,” etc.
41. 🧞Meet up and attempt 10 good deeds together in 3 hours. Be creative.
42. 📲Meet up in a public park and open up all the dating apps on your phones, attempting to convince someone to join you at the park as quickly as possible. First to successfully get someone to show up wins.
43. 🌊Channel your inner Avatar: the Last Airbender together and venture out to locations that best capture the energy of water, fire, air, and earth, e.g. a lake/river, a glassblowing studio, a sky lounge, and a quarry.
44. 👀Pick a neighborhood neither of you has been to, and seek to learn as much as you can in 3 hours about the history of that neighborhood. Check relevant articles on the internet, visit that town’s historical society, and go into nearby venues and ask the locals to share their stories.
45. 🕺Work together to positively change the course of one person’s life by virtue of asking them what’s been holding them back, and creating an action plan for working through it.
46. 🐶Visit a dog park and attempt to befriend as many floofy dogs as you can find. Be sure to make live commentary on the dogs’ social dynamics and internal monologues.
47. 🌻Volunteer for a day at a community garden and learn as much as you can about plants, soil, and other local community initiatives.
48. 🏘Wander through a neighborhood on foot recording yourselves making up an entirely fake and ludicrous history of what happened on each block. Bonus points if you can toe the line of believability so that if someone were to download your walking audio tour, they wouldn’t necessarily know that it’s all made up.
49. 🎧Download an audio walking tour and set out together on foot, wandering through your city with your headphones in, experiencing each other’s presence without the need for explicit words or direct engagement.
50. 💸Each of you pick a skill or hobby you’ve been wanting to practice or show off, and go outside busking across from one another for a few hours to see who can make more money from passersby.
51. 🏞Go to a public park and create a shrine together using only materials you can find at the park. It can be a shrine to a fallen leaf, to the spirit of a well-known local, or to a recently closed popup shop. Be creative.
52. 🎨Ask a local graffiti artist to take you on a street art tour of a neighborhood or two in your city, where they can explain what motivates graffiti artists, how they find good spaces to tag, and what inner drama happens in the world of street art.
53. 🌉Pick any 3 landmarks in your city and try to walk to all of them, with ample coffee breaks in between. For starters, try walking across all the bridges that connect Brooklyn to Manhattan in a single afternoon.
SEASONAL DATE IDEAS
54. 🎃Buy a pumpkin and some carving knives and learn to carve political messages into your halloween decor.
55. 🍎Go apple picking at a local orchard. If possible, bring a golf club and if there’s sufficient space, enjoy taking turns hitting the apples with the golf club (they explode — https://www.youtube.com/watch?v=10jMk-7IOB0).
56. 🧝🏾Visit a renaissance faire and see if you can randomly volunteer for something there that lets you either get a unique perspective/experience, or free renfair swag.
POTENTIALLY DANGEROUS DATE IDEAS
57. 🔥Attempt to go to hell in every major religion by doing one thing in each that technically guarantees damnation but doesn’t actually hurt or inconvenience anyone around you
58. 🏝Try to find and visit every naturally occurring body of water in your city, ranging from rivers, lakes, and streams to underground waterfalls. This may require some research, and potentially some trespassing.
59. 👨🚀Join up with a group of urban explorers to traverse an abandoned or under construction building late at night. Be safe.
60. 👨🚒For more active, hands-on experiences, consider rock climbing, archery classes, axe throwing, or a wrecking room.
61. 🕵️Be amateur detectives, consult your local police department or crimes bureau for any unsolved mysteries/crimes, and see what you can piece together using things like social media and basic querying of locals. If you like this idea but are way too lazy to go outside, just listen to the My Favorite Murder podcast.
ROMANTIC / NSFW DATE IDEAS
62. 🍳Meet up to watch Saturday morning cartoons in your PJs, cook breakfast together, then wander to a local park and lay on your backs watching the clouds. If there’s romantic chemistry, consider cooking breakfast mostly naked and snuggling during your post-breakfast food coma.
63. 🔤Create your own love language workshop together in realtime. Practice showing each other how you prefer to demonstrate love and care, first through sharing your own personal experiences giving and receiving love through each of the 5 love languages, but gradually escalate into practicing those languages on one another.
64. 👩❤️💋👨Agree to livestream your date, then, before the live recording begins, brainstorm how to create a ludicrously romantic, jealousy-inducing, Instagram-worthy date that will have everyone talking about it for years.
65. 🧖🏿Endeavor to learn tantra together. Agree beforehand that you’re not going to have explicit sex on this date, but that your communal mission is to practice the things around / related to sex that are mesmerizing, fulfilling, and deeply memorable.
66. 💗Take a half hour each to write a short erotica, then take turns reading each other’s story aloud. Then, each of you attempts to draw a scene from each of your stories. As a bonus, ask passersby in a park to read your stories, and if time permits, ask them to draw their own creative interpretations.
67. 🚿Have a sexy cleaning day. Pick one of your homes and try to make it as clean as possible from top to bottom, and strongly encourage moments of gentle touch, ample verbal praise, massages after particularly effortful tasks, and good playlist making. Ideally paired with a good, energizing strain of cannabis.
68. 🍑Volunteer to be nude models together for an art class.
69. 🙉Practice sensory deprivation together. Take turns blindfolding one another, wearing noise-canceling headphones, touching with no sight, sound, or words, and sharing silences together.
70. 🍆Each of you make a mad libs style depiction of your ultimate sexual fantasy, leaving out some nouns, adjectives, and verbs, then have the other fill in the missing words. Next, try to live out each other’s fantasy, but using the directives that the other person supplied. If you don’t feel comfortable doing so, attempt to find a comparable version of it online. If you can’t find it online, attempt to draw it yourselves.
71. 💆🏻Watch video tutorials on how to give deep tissue massages, then practice on one another. Ask for frequent feedback around things like stroke location, duration, and intensity, and showcase what each change might look like in order to be sure you’re doing it just right. For an hour each, dedicate yourself toward fully providing for the other’s needs. After you’ve exchanged these massages, if you’re both open to it, consider taking another hour for one of you to lay perfectly still, allowing the other to touch/observe/explore your body without any expectations.
HIPSTER AF DATE IDEAS
72. ☕️Buy some green coffee beans, and learn optimal ways to roast, grind, steep, and/or press them for the ideal cup of coffee. If available, attend a coffee cupping ceremony.
73. 📸Find a photography tutorial and set out together to attempt to take at least 50 photos each practicing each major skill, like composition, shutter speed, ISO speed, exposure, etc. If bold, consider escalating to nude photography. If extra bold, consider doing so in public.
NYC-SPECIFIC DATE IDEAS
74. 🎹Go to Washington Square Park to lay under street musician Colin Huggins’ grand piano while he plays.
75. 🌲Use a tree map (https://tree-map.nycgovparks.org/) to discover the oldest, tallest, etc. trees in your neighborhoods, and, if the feeling strikes, create a shrine near those trees.
76. 🚃Ride a subway to the end of the line together, then attempt to make it back to where you started without using the subway or any money.
77. 👩🏾🏫Attend a local free lecture or discussion series, like NYC Salon, Scientific Controversies, Caveat.nyc, OutInTech, Society for Ethical Culture, Joy List, Society for Ethical Mischief, etc.
78. 🚣🏿Take a free kayaking trip along the Hudson river and see if you can explore any of New York’s secret or abandoned islands or discover any birds along the Palisades cliffs.
79. 🧜Get kidnapped by pirates (not recommended, but at least you’ll have a crazy story). Some of NYC’s boat tours are operated illegally by opportunists and swindlers who pretend to be taking you on a “Statue of Liberty Tour” but actually just hold you hostage on the boat until you pay them to let you leave, then they sail away before you can consult the authorities. If you strategically don’t carry any credit cards or much cash on you, it’s possible you could succeed in being kidnapped on the cheap!
80. 🎭Wake up super early and rush a Broadway show. Rush tickets are frequently under $40, but expect to arrive about an hour or two before the theater opens, and potentially sit/cuddle out in the cold.
EXPERIMENTAL / HYPERSENSORY DATE IDEAS
81. 🙈Share a meal in which you only eat side by side and make no eye contact whatsoever, then afterward, sit across from one another and gaze into each other’s eyes for 5 minutes, with no words.
82. 🌮Go to a supermarket and, spending less than $15 each and without showing one another, attempt to collect the most intense sources of tactile and olfactory sensations you can find, then treat one another to a blind taste/smell/touch experience. Confirm possible allergens ahead of time!
83. 👐Set out together in search of the best possible tactile delights, from soft fluffy things, to squishy, sticky things, to bouncy things, to objects with satisfying acoustics.
POLITICAL/PROFESSIONAL DATE IDEAS
84. ⚖️If your political preferences are aligned, practice makeout political pomodoros, whereby you spend the 20 minutes calling your congressional reps and/or phone banking for Get-Out-The-Vote campaigns, followed by 5 minutes of passionate making out. Repeat as desired.
85. 📰Political scandal brainstorming! Think about various political issues you care about and create the theoretical groundwork for lawsuits that would call them to the public attention. For example, if you care about LGBT issues, in what state would it be optimal to legally back someone who recently got fired for being LGBT. If you care about widespread acceptance of non-monogamy, what state would be ideal for reaching out to someone who doesn’t feel safe sharing their relationship status at work and feels like a second class citizen with a gag order.
86. 👩🏻🔬Pick someone one of you knows in a career field that you both find deeply interesting, perhaps a field that one or both of you wanted to pursue but never ultimately did. Ask that person if you can both shadow them for the day, and see how much you can learn together. No making out!
87. 💪🏾Try to convince one of you, or one of your friends, to run for local office. Follow guides from http://runforsomething.net and see if you can not just convince someone to run, but actually get them onto a ballot within 1 day. This may involve a bit of paperwork and door to door canvassing to gather signatures, but you’ll both come away with an untold amount of newfound knowledge and wisdom.
88. 🧙🏻Attend / host a public hexing of Donald Trump (this was actually a thing you could do for $10 at Catland Books in Brooklyn in 2017)
89. 🥣Pick a cause you both believe in, and meet up to volunteer together for 3 hours with that cause. Soup kitchens are wonderful.
90. 👩🏾🎓Take an afternoon to reconsolidate your student loans together.
91. 🎗Pick a charity of your choice, and dedicate 1 hour toward seeing how creatively you could help that charity fulfill its mission. If you can get x number of people to sign up/donate in 1 hour, imagine what that means for anyone else you know who might want to support that cause.
92. 👩🏽💻Find a cozy coffee shop or coworking space, bust out your laptops or other creative materials, and commit to 4 hours of focused time working side by side on projects you deeply care about, like a new blog post, a creative writing sample, a painting, or a song.
93. 💳Create an “Adulting 101” seminar for one another in which you take turns walking each other through how to do various adult activities, like how to optimally pay taxes, how to create a Roth IRA, how to establish credit, how to write a check, and how to register to vote.
NERDY DATE IDEAS
94. 💭Self-mastery, together! Take 3 hours to answer as many personality inventory quizzes as you can, as part of a mutual quest to understand yourselves as fully as possible. Consider MBTI, Big 5, Enneagram, Socionics, Neurocolor, Attachment Style, Love Languages, StrengthsFinder, Belbin, True Colors, Political Compass, and the Harry Potter Sorting Hat.
95. 🧚🏿Find a Dungeons&Dragons dungeon master / venue and join for a night of creative gameplay and nerdy revelry.
96. 🧠Create a mind map together — list out the core pillars of your lives (e.g. mind, body, spirit, friendships, family, tribe, etc.), and keep creating lists to shine additional perspectives on how you view yourselves and your lives. Consider lists like “major energy sources vs. energy drains,” “where my attention lives each day,” “top fictional heroes whose qualities I want to emulate vs. top villains whose characteristics I currently share but want to actively create habits to mitigate.”
97. 📌Create a really fucking good Pinterest board together. If for porn, use Tumblr. [Update: Tumblr banned porn, so uh....got any suggestions for where to curate sexy things these days?]
TASTY & DELICIOUS DATE IDEAS
98. ♞Buy a chocolate chess set and play a game of chess together, eating the pieces that you capture.
99. 🍕Pick your mutual favorite food (pizza, ice cream, etc.) and curate your own walking tasting tour of it. Afterward, see if you can convince passersby to join your tour.
100. 🍷Go to a local wine/alcohol tasting, meet the owners, and learn as much as you can together about the nuances of what you’re drinking, and about the culture around that drink.
• • • • • • • • • •
I’m Steve Dean, an NYC-based dating industry consultant and relationship coach.
You can join my free weekly mailing list where I share dating industry insights, date ideas, relationship tips, new dating apps, founder interviews, and experimental projects and events I’m working on.
I offer customized consultations to individuals who need help with dating & relationships, as well as dating sites who need help with product strategy, partnerships, marketing, and growth.
I like to write and podcast about dating, relationships, and how to get connected to awesome jobs, roommates, and events. If you’d like to keep tabs on what I’m working on, you can follow me here on my website, or connect with me anywhere: