Depends on whether or not whomever I'm dating is okay with a mouth full of hair.
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What? Don't give me that look.
Okay, in all seriousness, it depends. Most of the time I just trim it all back. Other times I shave it off completely.
I don't have trouble with razor burn or itchy stubble. I'm quite deft and efficient with my shaving. (ironic, since I don't shave my face much) So shaving it all away doesn't bother me.
I never purposefully let it grow out. I'm a hairy guy. Not to Robin Willians levels but still fairly hairy. Letting it grow out just feels (and looks) gross to me, so I just don't do it.
On rare occasions I decide to have a little fun with it. I'll trim some areas and shave others to create patterns, words, or images. Weird, I know, but almost no one ever really seems them. They're mostly for my enjoyment.