It usually doesn't doesn't, which is likely why he apologized for joking during the conversation at the same time Reddit apologized for misinterpreting what was said on multiple levels (both in the same audio clip). The point wasn't it was the best tactic that could have been used, just that it was clearly not a serious ask on his part where he expected them to actually buy it.
And I don't like to talk to people uncomfortable with the idea I can verify what they said to me. Surveillance is one thing when it's a third party, but it's a completely different thing when it's the person you're already sharing the information with. In the former problems about who you intended to communicate with and a third party with more power than that initial two come into play, in the latter those don't exist (unless your goal is to publicly lie about the conversation and push the recording to be shared, as was done here, in which I have little sympathy for lamenting you can't rely on doing that with me). But yeah, not everyone agrees on this one. Even the law is highly varied in this regard.