Hi arieve,
Thank you for contacting Microsoft Community.
I can understand the frustration when things don't work as expected.
Just a few questions first, to get a clear picture of the issue;
- What is the Make and Model of the computer?
- Did you try headphones on any other system installed with Windows 8.1?
- Did you try to plug a different headphone to make sure that Headphone jack is working?
- What is the Make and Model of the headphone?
I would suggest you to follow the methods and check if these methods help in resolving the issue.
Method 1: Try running the hardware and devices troubleshooter
- Press Windows Logo + "W", type in "Troubleshooting" and press enter.
- On left pane click on View All.
- In the list, click on Hardware And Device to run the trouble shooter and follow the instructions.
Also I would suggest you to refer the link from Anshul Khanna replied on January 24, 2013for the same issue
Please do let us know if you need further assistance, we’ll be glad to assist you.