我昨天得跟一个女生睡在一起,那个可尴尬啊!I had to sleep with a girl yesterday, which was really awkward.

this 尴尬 means “shy” or “a little uncomfortable” ，but it is not insufferable. you can use 尴尬 in the situation that you have to do something although you are self-conscious about this situation， sometimes，at the same time you try to behave naturally and don't want to make this mood obvious. the first sentence should be “我昨天得和一个女生睡在一起，太尴尬了！” in real Chinese.

the second sentence may be have context... if only one this sentence appear i can not understand it‘s meaning.

他的尴尬的错误让他被开除了。His embarrassing mistake got him fired

this 尴尬 means the “错误” was caused distress to the company ，in fact that the company was embarrassed at the result "他的错误" made. 

there are still many subtle meanings，but i can't express them very well……you can ask more questions when you see a particular sentence includes 尴尬. 

good luck~_(:з」∠)_