Whenever I send a private message on this site, I'm never able to read them again or find them in the 'Sent Items' section of the messaging part. Does this mean my messages aren't sending at all or just aren't showing up there. Is there an option to enable this? Any help would be appreciated..I'm mainly just wanting to make sure my PMs are actually sending.

Thanks!

They're probably sending, you just need to tick the box that says "Save a copy of this message" before you send it. See screenshot:

oooh, you're probably right, I never noticed that before, how stupid of me lol.