I think you may be overthinking it a bit as usually someone willing to live in a basement will understand the potentially awkward situations you are describing.

It may seem awkward, but she now pays me $500 rent every month, and it has actually made things better between us.

It can be more difficult or awkward to infiltrate and you can often become "that guy" awkwardly standing on the outskirts, nodding in agreement (ask me how I know that :) ).

No thanks - I would rather poke my eye out with a rusty spork.It also means that I really like to communicate through text and email, but I always feel really awkward on the phone.Some day, I will figure out how to overcome all of this, but today is probably not that day.

Its just a very awkward thing to do is tell someone you smell so bad its offensive.

Now neither the attorneys that market these awkward, convoluted, expensive and administratively burdensome constructs, nor their victims who can't wait to jump into them at any price to prove to the world that they are a chest thumping real estate "player" would ever even begin to contemplate risk mitigation through the excercise of basic business due diligence activities. 

Made for an awkward ride home.

It has been very unsettling, I didn't get much sleep last night and I felt pretty awkward around his parents.

@Danual Berkley it feels awkward, but just do it!

It would just make for awkwardness if one party does not leave.