I dare say is defined on Dictionary.com as:
to venture to say (something); assume (something) as probable.
I've also heard of the expression dare I say it as well; however, I was unable to find a definition of it. Do they mean the same thing?
Although I understand the definition of I dare say provided, I'm not quite sure how, and in what context do you use it, and what does it convey.
Answer
They are closer to opposites. "I dare say" is a statement, meaning you are confident enough in what you are about to say to dare to say it.
"Dare I say it" is a question, because you believe what you are about to say will be regarded as controversial or may offend the sensibilities of the listen.
Example: "They made the first-ever matchup between unbeatens in the national title game — dare I say it? — a little bit boring." (source) In this case, the author is making the controversial statement that an important basketball game is boring, so she softens the shock of her words and reassures the reader she is still using good judgement by interjecting the "dare I say it?"
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