Date nights, handled for you
Retire “I don’t know, you pick.”
Wing plans the night around what you both love, so neither of you has to.
Free to start · No card needed · Works solo
Rapid Fire
Weekend vibe:
Pick one. Wing plans either.
A real Wing plan · River North, Chicago
Literary Whispers & Candlelit Plates
- 01after-words bookstoreBookstore5:30 PM9 min walk
- 02NonninaItalian dinner6:45 PM11 min walk
- 03Cafe CremerieGelato by the fireplace8:30 PM
Why Wing picked this
An unhurried, calm start that matches your preference for quiet, cultural places over noisy hotspots.
$140–200 · 3 stops · About 3 hours
Tell it what you love. And what you’d never do.
01 · You tell Wing
- Foodies(selected)
- Arts & culture(selected)
- Cozy nights(selected)
- Live shows
- Outdoors
- Nightlife
Hard nos
- Loud music
- Long drives
- Tourist traps
02 · Wing plans
Route at a glance
Literary Whispers & Candlelit Plates
- 01after-words bookstore5:30 PM9 min walk
- 02Nonnina6:45 PM11 min walk
- 03Cafe Cremerie8:30 PM
03 · You go
Friday? 👀
omg yes. I’ll book Nonnina
Send it as a link. They don’t need the app to open it.
- Stops checked on Google Maps
- Walking times from Google
- Reservation links included
- Swap any stop you don’t love
Your saved ideas, finally leaving the house.
Twice a week, Wing checks what’s on near you and turns the good stuff into plans.
Worth knowing nearbyWatershed Bar
River North
A candlelit, living-room feel made for close conversation.
Worth knowing nearbyL.A. Burdick
River North
Drinking chocolate so rich it’s basically ganache. Get one to share.
Worth knowing nearbyA gallery stroll
River North
Fits your love of arts and culture, and the walk between galleries is short.
And for the nights you stay in.
Quick games, small dares and a few memories worth retelling. Most of it is free.
Rapid Fire
Pet preference:
Pick one to see what they said.
100 questions. Answers stay hidden until you’ve both picked.
Dance together in the kitchen for one song.
Watch their favorite movie together, even if it’s not yours.
Ideas for the night you’re actually having.
Rainy, last-minute, kids asleep, or an anniversary coming up. Start with ideas, then let Wing turn one into a plan.
- How Wing plans the nightWhat a good plan includes · How Wing builds a plan
- The app for couplesWhat to look for in a couples app · What you can do in Wing
- Beyond dinner and a movieOut on the town, done differently · Make something together
- Fall, while it lastsGet outside while it lasts · Only in October
- AnniversariesCallbacks to your story · A proper splurge
- Nights out under $25Free or close to it · Under $25
- Nights inDinner that feels like an occasion · Play
- For parentsThe two-hour sitter window · Out during the day
- Tonight, no reservationFood without a booking · Things that are open late
- Rainy daysBig indoor spaces · Something active
- ReconnectingBe beginners together · Go into each other's worlds
Less deciding. More dating.
Your first plan is free. After that, Wing Pro is $59.99 a year for the two of you.
Free to start · No card needed · Works solo
Start soloInvite your person with a link or code, whenever.
Private by defaultYour answers stay yours unless you share them.
Nothing personal without your OKWing asks before using your answers to plan for you, and you can change it anytime.
Questions
The practical stuff.