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Ava, 27 Verified
River North ·
Online now
ArtArchitectureFine dining
Art curator with a weakness for architecture and late cocktails on the Riverwalk.
You mentioned the Art Institute — I was there Sunday. Impressionist rooms or straight to the modern wing?
Impressionists, always. Then coffee somewhere on Michigan before the crowds arrive.
Correct answer. There’s a rooftop two blocks from there that’s much better in the evening if you ever want to compare notes properly.
Your profile says you’re working through Randolph. How far down the street have you got?
About six places in. Still arguing with myself about the best one.
Thursday works if you want to settle it. Do you know the bar on Rush? Quieter than it looks and easy to get to from your side.
Genuine question — best new opening this year, and you can only pick one.
Anything on Randolph, honestly. I’m not helping, am I.
Not remotely. I’ll pick then, and you can tell me I was wrong afterwards.
You’re in Streeterville too? I walk the lakefront most evenings before it gets dark.
Ohio Street Beach end, usually. It’s the best view in the city and nobody agrees with me.
They’re wrong. The harbor looks best around seven, when everything goes gold.
Gallery openings in River North on a Friday — worth it, or too much of a scene?
Both. Which is sort of the appeal.
I’m five minutes from all of it, so yes. But I’d want a proper drink afterwards somewhere quieter.
You said unexpected first dates. Give me your best one.
Second City on a Tuesday is underrated. Half-empty room, much better show.
That is a genuinely good answer. I’d have said the conservatory in February, but I’ll concede.
Jazz on your profile — are we talking Green Mill, or the polite version?
Green Mill. Sunday, ideally.
Only if we’re there before the set starts. Walking in halfway through is a crime up there and I will not be part of it.
Restaurants on your profile. Am I allowed to ask where, or is that your whole personality?
It’s most of it. West Loop, mostly, and I’m stubborn about pasta.
I’ll never argue with someone about pasta. There’s a room in River North I think you’d like — no scene, very good kitchen.
The members shown here are illustrative examples of how profiles and conversations appear once you have signed in.
Discovery
Finding People Who Are Actually Nearby
Chicago is a city where twenty minutes in the wrong direction can end a connection before it starts. The chatroom is built around that reality.
Filter by neighborhood first
It is the most useful filter on the platform. Someone in Lakeview and someone in the West Loop are not going to meet on a Wednesday, however well the conversation goes. Start with people you could reach in half an hour.
Then by role and age
The role toggle splits the list into sugar daddies and sugar babies. Age filters narrow it further. Most members set a range rather than a number, which produces far better matches.
Sort by who is online
A green dot means they are in the app now. Messages sent to someone online get answered several times more often than messages sent into an empty inbox.
Look for the verified badge
Verification confirms that the person in the photos is the person in the conversation. It is optional, but unverified profiles are worth a slower approach.
Search by interest
Interests are the best predictor of a conversation that goes anywhere. Searching “jazz” or “architecture” finds people you will have something to say to on the first message.
Block and report from anywhere
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Opening well
How Conversations
Actually Begin
Almost every good conversation on this platform starts the same way: someone reads the profile properly and responds to one specific thing in it. Not the photos — the profile.
It works because it is rare, and because it gives the other person something concrete to answer. “Hey, how’s your week going?” requires them to invent the conversation. “You said the Green Mill — Sunday or Friday?” hands them half of it already written.
Keep the first message to two sentences and end with a question. Long opening messages read as effort pointed in the wrong direction, and they are much harder to answer.
A useful rule. If your opening message could be copied and pasted to anyone else on the platform without changing a word, it is not ready to send.
What a good opener looks like
EthanYou mentioned the Art Institute — I was there Sunday. Did you make it to the Cézanne prints? I thought the early still lifes were badly underrated.
AvaI did, and I completely agree — everyone walks straight past them. Are you a museum morning person or an afternoon one?
EthanAfternoon, always. It gives me an excuse to find decent coffee first. Any recommendations near the Loop?
Specific reference → genuine response → open question.
Before you meet
Four Things Worth Settling in the Chat
None of these are difficult conversations. They are only awkward if you leave them until you are already sitting across a table from someone.
Where, when, and how you both get home
Agree the place together rather than announcing it. Pick somewhere public and reachable for both of you, and arrange your own transport in each direction. Chicago evenings are much easier when nobody is depending on a lift.
How much you are each sharing
Plenty of members meet for the first time knowing only a first name and a neighborhood, and that is entirely normal here. Say what you are comfortable sharing and let the other person do the same.
Anything that is not up for discussion
One clear line stated in the chat saves an uncomfortable moment later. Anyone who argues with a boundary in writing will argue with it in person — which is useful to learn before you have committed an evening.
Green lights
- They answer questions directly, including the awkward one
- They offer a choice of public places rather than one location
- They accept a slower pace without commenting on it
- They agree to a short video call before meeting
Report and block
- Any request for money, bank details or gift cards
- Pressure to move to another app immediately
- A private address proposed for a first meeting
- A bad reaction the first time you decline something
Coverage
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