Break the ice by doing something together
A previous post talked about ensuring you appear available, which means not disappearing into your phone while you wait. However, sometimes just sitting and talking can feel intimidating for some people. If you know the person finds this difficult then arrange to do an activity together, such as walking the dogs, playing pool, going to watch a game, doing crafts etc. Doing something together creates an unspoken connection of energy between you beyond words, which as in my previous post, only forms 20% of the communication. It enables you to connect on less intense subjects first building a relationship in which you can eventually deepen the conversation.
Coming together this way can enable somebody to feel less lonely in itself. But it also enables a more relaxed approach to talking.