AI date planner for couples

Retire “I don’t know, you pick.”

Wing plans the night around what you both love, so neither of you has to.

Plan our next date

Free to start · No card needed · Works solo

Two people sharing bread over pasta and wine at a candlelit tableA couple under a pink knit blanket on the sofa, with tea and a record player glowing

Rapid Fire

Weekend vibe:

Pick one. Wing plans either.

A real Wing plan · River North, Chicago

Literary Whispers & Candlelit Plates

  1. 01after-words bookstoreBookstore5:30 PM
    9 min walk
  2. 02NonninaItalian dinner6:45 PM
    11 min walk
  3. 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.

  1. 01 · You tell Wing

    • Foodies(selected)
    • Arts & culture(selected)
    • Cozy nights(selected)
    • Live shows
    • Outdoors
    • Nightlife

    Hard nos

    • Loud music
    • Long drives
    • Tourist traps

  2. 02 · Wing plans

    123

    Route at a glance

    Literary Whispers & Candlelit Plates

    1. 01after-words bookstore5:30 PM
      9 min walk
    2. 02Nonnina6:45 PM
      11 min walk
    3. 03Cafe Cremerie8:30 PM

  3. 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 date ideas, finally leaving the house.

Twice a week, Wing checks what’s on near you and turns the good stuff into plans.

  • Two cocktails on a walnut bar beside a turntable and shelves of recordsWorth knowing nearby

    Watershed Bar

    River North

    A candlelit, living-room feel made for close conversation.

  • Two cups of drinking chocolate and sugared doughnuts by a fireplace, city lights outsideWorth knowing nearby

    L.A. Burdick

    River North

    Drinking chocolate so rich it’s basically ganache. Get one to share.

  • A couple looking at a large pink and ochre painting in a galleryWorth knowing nearby

    A 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.

A couple dancing barefoot in a warm kitchen at night, mid-spin

Dance together in the kitchen for one song.

No phones, just the two of you.

Watch their favorite movie together, even if it’s not yours.

Sometimes love means “The Notebook” again.

Less deciding. More dating.

Your first plan is free. After that, Wing Pro is $59.99 a year for the two of you.

Plan our next date

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.

  • AI only with your OKWing asks first, and you can change it anytime.

Questions

The practical stuff.