Update, after looking everything over we didn't see any problems so we decided to give it a firm push to the left and it did lock. I rode the bike to my friends house and everything felt fine. Thank you everyone for your comments.

 

The old saying goes something like; Locks are only meant to keep the honest man honest.
The barrel locks on our bikes are not that hard to defeat/pick. Amazon and/or ebay sell the tools and youtube has plenty of how to videos.

 

The first picture shows the lock hole (with no lock in it) and how it doesn't align with the bottom hole. The second picture is when you apply pressure (to Compress the rubber stop) the hole aligns with lock for proper engagement.
When you try to unlock it without putting pressure on the bars to the left it binds the locking pin and damages the lock.
I'm switching this one because of that reason. there's a small pin in the lock mechanism that raises the locking pin and it's easily broken.