Difficult to use, do, or deal with2
“I need to have an awkward conversation with my boss.”
“It was an awkward negotiation, but we figured it out eventually.”
“He’s an awkward customer” (a difficult person to deal with).
2 Causing or feeling embarrassment, worry, or inconvenience3
“You have put me in a very awkward position.”
“Her suggestion was followed by an awkward silence.”