So I have some decent headphones that, when connected to my phone

>>49261
Make sure there's no debris in your phone jack. Blow it out with a bit of compressed air. All else fails, get a new phone

or bring your phone to service center to replace your female headphone jack

>>49281
This, also try isopropyl alcohol and a pipe cleaner, be careful with this tho, you just want to get it clean but the jack internals are fragile.

File: 21kjHQ7i0mL._AA200_QL65_.jpg (4KB, 200x200px) Image search: [Google]

4KB, 200x200px

Have you tried using a short extender?

Dust and sand was my issue a couple of times so def try to blow it out or shake it.

File: Female jack off - Closeup.jpg (72KB, 1024x768px) Image search: [Google]

72KB, 1024x768px

>>49261
If it's not dust, try to use a needle as a lever to make sure the prong inside the female jack makes contact with the male one. It can sometimes be flattened to the side. See pic.

>>49362
This. It could also be a dodgy solder bond on the headphone jack. If it is a consistent problem no matter how many sets of headphones you throw at it and it has warranty, jump on it. Remember to back it up and factory it before you hand it over.