Hi pitchfork,
Thanks for contacting Apple Support Communities!
We understand that you' re unable to use your headphones consistently with your MacBook Pro.
Do you have access to another set of headphones you can use to test with your Mac?
You can also run a diagnostic test on your Mac to ensure that the audio hardware is functioning as expected to help isolate this behavior further: Use Apple Diagnostics to test your Mac
You can also create a new user account on your MacBook to test your headphones. This will let us know if this behavior is system wide or isolated to one user.
To create a new user account, you can go to the Apple menu > System Preferences, then click Users & Groups.Click the lock icon, then enter an administrator name and password.Click the add button (+) below the list of users.Complete the fields shown for an Administrator account, then click Create Account (or OK).Once you’ve created the new account, go to the Apple menu > Log Out, then log in with the new account.
If you're unable to reproduce the same behavior in a new user account, you can troubleshoot your login items as outlined here: Remove login items to resolve startup problems on your Mac
We hope this helps.
Cheers!