Updated 30 August 2026
Random chat on PineappleChat
Random chat here means a live, one-to-one conversation with someone on the People list — not a noisy public room. If you want a group conversation instead, open Rooms: registered members create rooms, and guests and members can join public ones. PineappleChat is free, 18+, and runs at pineapplechat.com.
How a random chat starts
- Open the site and set a username, age (18+), and location.
- Look at who is online (and who is away for a short grace period).
- Tap a person. You do not need an account for a live chat.
- If you like them and both of you register, you can move to friend chat.
Guests and members in one list
Unlike sites that split “anonymous roulette” from “members only”, PineappleChat shows guests and registered members together when they are in chat. A guest can message a member who is online. To message someone who is offline, you need a registered inbox.
Hidden mode
Turn on Hidden to stay off other people’s lists. You still see others. After you send someone a message, they can see you, receive the message, and reply — even if they are hidden too.