He has symptoms of a urinary tract infection (i.e. feels like he needs to urinate when he doesn't and some pain urinating), but he was prescribed antibiotics twice and they unfortunately have not helped the situation. what else could be the issue?

Was a urine culture done? If not, it is time to get a urine culture to find out what the organism is that is growing in the urine and causing the infection. If the urine culture doesn’t grow any bacteria, then the symptoms are not due to a UTI. If this occurs, a urologist should be seen to find out what the symptoms are due to so it can be treated. Good luck to both of you!

There are many reasons which can cause this- stone, anxiety, local irritation etc. If persists needs to see a Urologist for proper management