If env ruby is Ruby 2.0 or 1.9, try either:
- Editing PATH or TM_RUBY in Preferences > Variables.
- Changing
#!/usr/bin/env rubyto#!/usr/bin/rubySource > Menu Actions > Comments > Comment Line / Selection.
Or try temporarily deleting bundles. From [TxMt] TM2 error running Comment Line/Selection - Google Groups:
Your bundles are likely messed up.
The TM_SUPPORT_PATH comes from the Bundle Support bundle, so you may have uninstalled that.
You can check Preferences → Bundles or remove ~/Library/Application Support// and relaunch to get back to defaults.
TM_SUPPORT_PATH is something like ~/Library/Application Support/TextMate/Managed/Bundles/Bundle Support.tmbundle/Support/shared. Try running echo $TM_SUPPORT_PATH or env with ⌃R.