Probably depends what country you're living in - in the UK, 'been around the block' is now an urban phrase which refers specifically and most commonly to sexual activity, although originally, I believe it was intended to be used simply to mean you've had former experience of other particular subjects. You might more easily say 'I know you've been around the block a few times, so you know what this task involves?' which is less stilted, but if you're in the UK, particularly in London UK, probably best not to use the phrase at all.
Answer from Bamboo on Stack ExchangeProbably depends what country you're living in - in the UK, 'been around the block' is now an urban phrase which refers specifically and most commonly to sexual activity, although originally, I believe it was intended to be used simply to mean you've had former experience of other particular subjects. You might more easily say 'I know you've been around the block a few times, so you know what this task involves?' which is less stilted, but if you're in the UK, particularly in London UK, probably best not to use the phrase at all.
In the US this is a very common expression to describe someone who has had plenty of experience, and especially someone who has seen the various ways that things can go awry, and so is not surprised or put off by them.
http://www.macmillandictionary.com/us/dictionary/american/have-been-around-the-block-a-couple-of-a-few-times
...or...
http://idioms.thefreedictionary.com/have+been+around+the+block
...I've heard this expression countless times so I'm a little surprised at some of the comments that express unfamiliarity with it. FWIW, I'm in the US northeast - New York / Boston axis.
Do people in the UK use the phrase 'round the block'?
around the block | WordReference Forums
what does"around the block"mean?
what does"around the block"mean?
The translation here says"it means you are really experienced in some fields"
The full sentence is"I know you've been around the block before and I know you've tried a lot to improve, I get it."
but I think it means "you are in difficulties"
What does "she's been around blocks. She's a beautiful mass" mean?
For context, I have one American parent and one British parent. They both use this phrase meaning going around a block of houses in one area. eg. 'I'm just going for a walk around the block' or 'There's no parking spaces here, we'll have to go round the block one more time'.
I grew up in England and I don't think I've ever heard any of my friends, acquaintances or generally people outside of my family use this expression so am wondering if this is something my American parent has passed on to my British family or if I am just ignorant...