I might just upgrade arduino to the latest version and hope for the best. I thought this might have been a known thing i couldnt find
Well, there is a known problem where 1.33 doesn't install/update the serial driver on some Windows 7 & 8 machines. The 1.34-beta installers fix this issue. There's also a mysterious problem that sometimes comes up with Macs. Missing driver on Windows results in no serial monitor communication, but you can still upload (all uploading is done by HID protocol, not serial). The Mac mystery causes partial data loss, but some/most of the data Teensy sends does seem to end up in the serial monitor.
But we can't tell if you're running on Mac, Linux or Windows, and if Windows, whether you've got 7, 8 or 10. We have no clear idea of the problem you're seeing, only "will sometimes work but most of the time not". We can't tell if your problems are only with getting text into the serial monitor, or if uploading code is also problematic. I want to help you, but you're really keeping all of us in the dark which makes it almost impossible to offer any helpful troubleshooting advice. Hopefully this first paragraph at least answers your question.
If you want useful help, you really need to understand this isn't how we do things here. You can see in many prior threads we have a pretty good history of figuring out problems on this forum, but the process involves posting very clear and complete info about what's really going wrong. We can't see your screen and can't know exactly what steps you're trying, unless you show us. It's important to SHOW us (as opposed to merely telling us) what you're doing and really seeing, because the insight into problems almost always depends on the small details.