Earlier quoted context omitted.
> but I refuse to let anybody know that I want to communicate with Bob That's not the problem though. You're not trying to stop an eavesdropper knowing you're communicating with a particular server, but rather which hostname you're talking to them as. To extend the Bob analogy; you're not trying to hide that you're communicating with Bob, but that you're speaking to each other as members of Fight Club. It's certainly…
You say "difficulty", the evidence seems to suggest impossibility. I am 100% certain that if you have an actual plan for how to do this without an extra round trip the TLS WG wants to hear about it (but please read the draft with the problem statement first so that you don't embarrass yourself and propose something that doesn't actually solve the problem) In order to be sure we're talking to Bob, so that it's OK if B…
Of course, this approach would require the DNS record is authenticated, so DNSSEC is a must, added to which the DNS resolution must be encrypted, so DNS over HTTPS, DNSCurve, etc.