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.

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Do people in the UK use the phrase 'round the block'?
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December 1, 2020
around the block | WordReference Forums
Hi If somebody says: The shop is around the block from the restaurant, it means you have to leave the restaurant, pass one block and there you'll find a shop? More on forum.wordreference.com
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November 25, 2010
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"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 More on italki.com
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October 23, 2017
What does "she's been around blocks. She's a beautiful mass" mean?
been around the block General: You have experience. Insult: You have had many sexual partners. beautiful mess You are unorganized, currently not at your best More on reddit.com
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November 21, 2019
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TheFreeDictionary.com
idioms.thefreedictionary.com › have+been+around+the+block
Have been around the block - Idioms by The Free Dictionary
To have experience, either in a particular area or in one's life overall. Yes, the new hire is young, but she's been around the block. She was managing a whole department at a prominent PR firm before she came here.
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Reddit
reddit.com › r/askuk › do people in the uk use the phrase 'round the block'?
r/AskUK on Reddit: Do people in the UK use the phrase 'round the block'?
December 1, 2020 -

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...

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WordReference
forum.wordreference.com › english only › english only
around the block | WordReference Forums
November 25, 2010 - In standard American English, if something is around the block (for a square or rectangular block) it means you make two turns and wind up on the opposite side that you started from. Around the corner is only one turn.
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Merriam-Webster
merriam-webster.com › dictionary › block
BLOCK Definition & Meaning - Merriam-Webster
5 days ago - 15th century, in the meaning defined at transitive sense 1a · Time Traveler The first known use of block was in the 14th century · See more words from the same century · been around the block · big-block · block and tackle · block capitals · block copolymer ·
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Quora
quora.com › What-does-I-ve-been-around-the-block-a-few-times-mean
What does “I’ve been around the block a few times” mean? - Quora
Answer (1 of 9): Hey, Chelsea. Come on, you’ve been around the block a few times and you want me to believe you do not know what it means. Or maybe, you are a guy but then you guys get around a lot too. Okay, I shall take your word for it. So, the form: the subject has/have been around the bloc...
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Cambridge Dictionary
dictionary.cambridge.org › dictionary › english › block
BLOCK | English meaning - Cambridge Dictionary
1 week ago - My friend and I live on the same block. ... I took a walk around the block.
Find elsewhere
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Urban Dictionary
urbandictionary.com › define.php
Urban Dictionary: around the block
October 14, 2007 - around the block: A term for a woman who has sexual experience.
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Cambridge Dictionary
dictionary.cambridge.org › dictionary › english › new-kid-on-the-block
A/THE NEW KID ON THE BLOCK - Cambridge English Dictionary
1 week ago - A/THE NEW KID ON THE BLOCK definition: 1. someone or something that is new in a place, organization, or situation, usually one in which…. Learn more.
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Reddit
reddit.com › r/englishlearning › what does "she's been around blocks. she's a beautiful mass" mean?
r/EnglishLearning on Reddit: What does "she's been around blocks. She's a beautiful mass" mean?
November 21, 2019 - It is "She has been around the block" which means that she is experienced, but it has a somewhat bad connotation to it, as in she is used up.
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Plain English
plainenglish.com › home › lingos › around the block
Around the block | Expression in English
April 25, 2024 - This means that he has a lot of experience in politics; he’s not a newcomer. When you want to say someone has experience and knows what he or she is doing, you can say that person has been around the block.
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GRAMMARIST
grammarist.com › home › idiom › been around the block
Been around the block Idiom Definition
September 14, 2024 - The idiom originated in the 1960s, probably in America, where neighborhoods are organized in blocks, which are squares or rectangles of land with evenly spaced houses. Be careful when you use the term been around the block. In some circumstances, the phrase means the person in question is sexually experienced.
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UsingEnglish.com
usingenglish.com › home › grammar reference › idioms › b › been around the block a few times
'Been Around The Block A Few Times' Meaning - UsingEnglish.com
Someone who says they've been around the block a few times is indicating that they have life experience relating to the topic at hand. It is not necessary to discuss the introductory aspects of the topic or give beginner level advice.