Is it really awkward to encounter someone you know outside of the context in which they are more familiar? It would be awkward to walk up to the girl just as she was saying to another student how much she hates me. That could be an awkward conversation. No, I would think, "Well this is a coincidence" would be more fitting of such an encounter.
Kids use this word so much it has lost all meaning. If there is a pause in the conversation: "AWKward" (in a sing-song tone). Something strange or unusual: awkward. Awkward, awkward, awkward.
I wouldn't bring it up, but i just discovered the word in the writing of someone I consider to be quite a wordsmith. Perhaps it was used correctly, but now it bugs me so much that it rubs me the wrong way whenever it is used.
BUT...I do have something particularly AWKWARD to share.
This is a neighborhood not unlike many others in suburban America. It becomes an awkward neighborhood, however, when the points are explained. (A) represents my house. This is the house Heather and I lived in before the divorce. (C) represents Heather's new house. It's a logical enough choice, I suppose, given that she wanted a place that wasn't far from the area the boys have lived in for so long. It's only a couple blocks away from my house. That's not terribly awkward, since we get along pretty well and don't see each other all that much despite the proximity. It's even convenient in many cases. No, it is awkward because (B) represents Brandi's house. That's right: she's smack dab in the middle of it (often in many more ways than one!). It sometimes strikes me that it's a bit awkward (odd, curious, etc.) that the woman I used to be married to and the woman I am currently dating live, quite literally, a stones throw away from each other.
So when you think something might be considered awkward, stop and consider if it's similarly cringe-worthy, or if another adjective might do.
