In gay chat, "live" or "real" means a real meeting, usually for sex.
Those who chat with each other and at some point decide that it would be exciting to meet live, plan a real date of the face-to-face variety.
Depending on the context and chat portal, "live" can mean either a classic date, a rendez-vous or a One Night Stand be understood.
Accordingly, it is always useful to briefly check what the other person is planning before the live meeting.
To get a little taste of the live date, it can be worthwhile to go live beforehand in another form - namely via webcam. Here is from standard conversations to Dirty Talk or masturbate (depending on the platform) just about anything is allowed.
In order to actually be convincing on a live date, it is important to observe a few rules. For example, no one should be particularly surprised by their counterpart at the real meeting. If you claim to be "extremely funny", "sporty" and "witty", you should also be able to keep these high standards at the real meeting.
The places that are suitable for meeting live can be of many kinds. Some prefer a restaurant, others an abandoned car park. The different locations make it easy to draw conclusions about the direction the evening is likely to take.
However, there is usually no fixed period of time after how many chats a live meeting should take place. As is so often the case, the famous gut feeling is decisive in the last step.