(Actually) Unique Date Ideas
Not the same ones you’ve read a million times.
♥ ♡❦
Good morning friends and lovers.
We hope you enjoyed our very first letter, Single in a World of Couples, which was published last week. It was an introspective piece which captured a complex feeling that might be familiar to single readers.
We also heard your feedback: three readers found it relatable; two felt that the piece leaned too heavily towards the pessimistic side of being single; one found that it made them quite sad (sorry); another said they felt more empowered in their single life after reading. Quite a spread! We love to hear all the feedback — negative, positive, whatever. We’re still finding our footing for First Impressions, but one thing we’re sure of is that it’s NOT a one-way channel
Today, we picked a topic that’s much lighter, with a more practical focus.
Our goal for this list is to share some TRULY unique options to break you out of the boring date cycle. Note that some of these ideas are fairly… involved; they might be nerve-wracking to introduce, especially to a total stranger. Others are quick ideas that could be brought up spontaneously during a normal date to liven things up. Keep the latter in your back pocket.
Many of the options will take you and your dating partner a little outside of your comfort zone, but if they didn’t, this list would be the same old boring stuff you’ve already read. These will help to break down barriers and get you past that third date lull. Let’s spice things up!
We’ve broken the ideas down into First to Third Date territory, where you might want to play it safer, and Fourth Date onwards, where you can get more freaky. Of course, these are arbitrary guidelines. You’ll know what works best for you.
First to Third Date Territory
🎥 Movie in the park. Starting with a super safe one that’s not unique, but SO underrated. Every city has these! Bring olives, cheese, and a bottle of something nice. Here is a list of ones available in NYC:
🖼 Attend gallery / museum openings and book release parties. Again, on the safe / unoriginal side, but there are countless of these almost every night in NYC, and it’s great to support your local arts scene. Also, they serve as great icebreakers: low pressure, open-door policy, something to look at and discuss, often free wine. Great people watching as well. If you’re nervous about having something intelligent to say about the art (which is NOT necessary), do some quick research on the show(s) you’re planning to attend.
🪄Show & Tell. Once you have an idea of mutual interests, set up a date where each of you brings a beloved thing within the category of mutual interest you have. Ideally whatever is brought can be consumed, or at least presented in some way, during the date. For example, records, wine, video games, a passion project. Leave some space for each person to explain the thing they brought. Why they love it, the story behind it, etc. Listen and ask questions!
Sample message: I feel like when you were talking your app idea last night you didn’t want to bore me… but I found it so interesting! I was thinking for our next hang you could show me your initial designs and tell me more about it? I’ll even do the same with my little side hustle.
🃏 Get a Tarot reading done or visit a mystic together. This is guaranteed to prompt some interesting conversations when you debrief after. If you’re feeling brave, ask them to interpret your dating future(s).
📝 Errand dates. Highly underrated because, let’s face it — we’re all busy. Go about your normal running of errands with someone in the early stages of dating. It takes a lot of pressure off the date as you can just chat and they can see you in your natural environment. AND you get shit done. This might sound exploitative on the surface, but the invitation can actually be very charming, as it feels like you’re letting the person into your life. Remember — if you can have fun with them doing mundane stuff, it’s a very good sign.
Sample message: I’m doing groceries in a few hours and think it would be so much more enjoyable if you came along!
🛋 Go to estate sales. Especially in cities like NY where there are so many eclectic characters around, you can find estate sales of every kind in your area. And yes… an estate sale is a liquidation sale of someone’s property after they pass away. But it’s not morbid! This is more of an adventure than your typical shopping or thrifting date, as you’re entering someone’s space, perusing often personal objects, getting to participate in auctions, and (sometimes) walking away with incredible + affordable finds.
Fourth Date Onwards
🛣️ Night drive. Pick an album you want to listen to, front to back, and go for an aimless drive. Don’t make a plan for stops, just pick a direction and go. Ideally a route neither of you take very often. When you’re staring at an open road ahead of you, conversation has a habit of opening up and being more intimate. And perhaps you’ll make some spontaneous stops along the way that will be memorable. Carshare programs should allow you to do this pretty affordably if you don’t own a car!
Sample message: Hey, last time we hung out you were telling me about the new FKA Twigs album. Haven’t listened yet, but I was thinking tomorrow night we could go for a drive and listen? We can stop for dinner or snacks or a picnic or whatever.
🧑🏽⚖️ Night bosses. Break the date into two segments. One person is the boss of the first segment, the other is the boss of the second. Alternatively, you can alternate being bosses for separate dates. The boss is responsible for ALL plans during their segment, is in charge of vibes, and has final say on every decision. This helps with indecision during the what do we do next? phase. With strong communication and ground rules, this can be taken back to the bedroom.
Sample message: I love our democratic date planning, but in the spirit of 2025, lets dabble with some authoritarianism. I’m electing you as night boss for our next date. You can pick anything you want to do, and get final say on every decision for the night. If it goes well, I’ll take over next time. Shall we try? 😈
🔪 Iron chef. Each person buys a secret ingredient for the other (make sure to set a budget first!), then reveals it at the start of the night, for the other to cook a single dish with the ingredient chosen for them. Combine your dishes for your dinner date. No recipes allowed, just whatever ingredients are in the kitchen. A great way to find out who's a more creative and intuitive cook! If this is too stressful, the same can be done for cocktails.
👤 Pretend I’m not here. One person goes about their night exactly as they would if the other wasn’t there, and the other person just tags along. This is the Errand Date on steroids. It’s not only revealing of what a person is like behind closed doors, but it adds a layer of intrigue to what would otherwise be mundane. Remember — if you can have fun with them doing mundane stuff, it’s a very good sign. Plus, it’s simple and low pressure.
Sample message: Weird idea… but can I just like, chill with you while you go about your regular weeknight routine? I love our high effort dates, but can tell they take a lot out of both of us with our schedules. Would love to just see you exist the way you do without me around!
👗 How would you dress me? Give the person access to your wardrobe and get them to put together what they consider the best outfit available in your collection. And vice versa. Great way to see the differences in your tastes. And who doesn’t love a game that involves dressing / undressing?
💗 Volunteer at a soup kitchen, or a park clean-up, community garden, or similar. Dating tends to be very consumption-oriented. It can be a fantastic change of pace (and romantic!) to give back to the community.
Sample message: Hey, I’m planning to volunteer at the Food Bank next week. I try to go every couple months and it’s actually such a fun group of people. Would love for you to join!
🖌️ Sketch Each Other, No Matter Your Skill Level. Bring notebooks to a bar, café, or park, sit across a table, and attempt to draw each other. Guaranteed you will learn something new about the other person’s face. And you better believe that staring at each other for a while will build some (good) tension.
That’s all for now!
Did this list get your creative juices flowing??? Or have an idea that we missed??? Share your ideas and thoughts in the comments, or by replying to this email, and we’ll feature them in a future post and credit you ofc :)
Happy dating,
- Cheers
♥ ♡❦
