Same thing is happening to me since last week. Maybe it has to do with last update of the watch? It connects and I can use the control of the headphones for playing, pause... but no sound.
I had this problem, too. When I went in, maxed my headphones and also amped up the volume on the FR645M music screen, I had more than enough volume. My different headphones seem to interact with the music source differently.
This has happened to me since 3.10 & now in 3.40. Rebooting watch temporarily solves the immediate problem of no sound but does not resolve the underlying glitch in the software. Garmin has yet to respond to any comments on this particular issue. I even sent an email to garmin that went unanswered.
The continued beta testing on this $500 watch is seriously grating.
Same problem this morning with my 465M fw:3.40. - My headset (Divacore Antidots) where successfully connected, but no sound. - Action on my headset (pause, next song..) worked, but no sound - The Sound menu was "strange", text like "press + or - to change volume" but no gauge. Because I was in the midle of my training, I couldn't reboot ... -> Ok now after reboot Hope it will not happen again !