Planning dates is pretty hard thing to do. Sure, it’s easy to just randomly pick a place and time and say “let’s meet here and do this”, but planning dates with strangers is rarely that easy. You might have a list at hand for things to do or see when a friend wants to hang out, but planning a date can be a bit more nerve-wracking. You’re navigating around the perceived preferences of a relative stranger to plan something you hope will, maybe not impress them, but at the very least give off a good impression. If my description gives you more anxiety, sorry about that. The good news is, I’ve got some date ideas I think you’ll love.
Your mileage may vary based on the city you’re in, the abundance of nightlife or cultural options, so feel free to adjust these ideas as you see fit. Think of this less like specific recommendations, and more like ideas that should work as a framework for planning future dates.
First, some basic guidelines for what to do on first, second, and third dates.
This is what you should shoot for on a first date. An activity or venue that allows for communication, one that will leave a good impression that reflects you as a person, and something you’ll be comfortable doing. Avoid movie dates or anything else where you can’t really talk, avoid spending way more than you can afford on a first date, and avoid doing something that makes you so uncomfortable you have a bad time.
A second date should build on the first date, though what you do on that date is entirely up to you. Communication, good impression, doesn’t make you uncomfortable. What you do isn’t nearly as important as continuing to set a good precedent, and figuring out whether you like the person you’re on a date with.
Third date is the milestone for when you can finally mix things up a bit. By this point you probably have a good idea as to whether you like them, and they like you, so throw the rules out of the window.
So with that out-of-the-way, let me give you some date ideas that I think you’ll love:
The Cocktail/speakeasy date
Confession for you, I’m not the biggest fan of “speakeasy” style bars. My annoyances with how contrived they are aside, cocktails/speakeasies tend to make for great date venues. Primarily because they’re not rowdy, you can usually find somewhere to site, and while the cocktails tend to be a bit pricey, they’re not exactly “buying bottle service” level prices.
If you happen to be in NYC and want to go on a cocktail date, I’d recommend Weather Up. Either the Brooklyn location, or the Manhattan location.
The Hidden Gem date
While a cocktail speakeasy date is one that is likely to impress your date, it probably wont tell your date much about you. A hidden gem date should accomplish this. Planning a date around a place you consider a hidden gem is a great way to show your date a bit more about your personality.
It’s hard to call any successful bar or restaurant in NYC a “hidden gem”, but bear with me. Mission Dolores, Pig Beach, Lavender Lake, and Livingston Manor are maybe not hidden gems, but not so popular that you can’t walk in and grab a drink.
“This place has the best…” date
This type of date is less about impressing your date with the ambiance of a place, and more about impressing your date with the quality of this place. That quality can be the food, the music, the drinks, the coffee, whatever you think is appropriate. This sort of date works especially well if someone mentions something that they like that corresponds with a place that you know that has the best version of that. If the place that has the best version of something isn’t the best venue for a date. If that’s the case, plan a second stop for your date and let your date know. i.e. I remember you telling me that you love pizza so let’s go here since they have the best pizza, then we’ll grab a drink afterwards.
Here are some of my recent favorite “this place has the best…” spots: Taqueria St. Marks in Manhattan. Their suadero taco is the best taco I’ve ever had, bar none. ALSO: Bunsmith in Brooklyn (both in Prospect Heights and in City Point) has the best damn pork jowl bun I’ve ever had, and they carry one of my favorite beers, Stillwater Artisanal Extra Dry Sake Style Saison.
The walking/cultural institution date
The walking/cultural institution date might be harder to pull off in some places compared to others, but it’s a good one. And no, it doesn’t have to be a last resort date because you’re broke. You can plan a date that involves walking around, or hanging out at a cultural institution (museum, park, etc.) and not have it seem cheap.
Here’s a few ways to pull it off in NYC. Pair a walk on the High Line with a trip to the Whitney (it’s right next to it and costs $25). Or do a walk up the High Line and then go to Frying Pan for drinks. Or take a walk around Prospect Park, pop into the Prospect Park Zoo (it’s like $8), then head into the Brooklyn Botanic Garden and then the Brooklyn Museum of Art ($25 ticket for both). Or, create your own brewery crawl in LIC by hitting up Big Alice, Transmitter, Rockaway, and LIC Project, then take a walk through Gantry Plaza State Park.
The Seasonal date
I have no clue what the weather is like where you live, but up here in NYC, as of the date of this post, it’s getting very autumnal. The perfect weather for dates in bars with fireplaces, or walks through nature to see the changing leaves, apple-picking, and so on. In the summer, go for dates on rooftops or other outdoor spaces.
So there you have it. Now go forth and plan a great date.
Good Luck Out There.
Also published on Medium.