This is intentionally only included in Forum-mode chats in Briar. Over direct message, leaking contacts is considered a breach of security. (Your definition of "leak" may differ.) In group messages, only the group admin is considered trusted, and every message must go directly to or come from them.
In every security tradeoff, Briar chose the option that maximizes security, even considering how the airwave transmission times might be fingerprintable as Briar traffic.
Not saying any of this is a good way to make a useable app for wide adoption, but it is intentional and highly opinionated.
The use case for allowing 1:1 DMs to be exchanged via courier is to maximize OpSec for whatever messages are being exchanged - I may trust Bob to deliver a message, but Bob may not need to know the message content.
The feature could include marking "approved couriers" per contact, perhaps? Both Alice and Charlie would have to set Bob as an approved courier for message exchange to each other.