Usage of the idiom "around the block"

Question

I know of the idiom around the block, but I'm having some doubts as to whether I can use it in certain ways. More specifically:

1. Can I use it in a phrase like "This is not your first time around block", to indicate that the person has done this before?
2. If yes, then how informal is it? I mean, can I write to a colleague about a certain task something like "Since this is not your first time around the block, you know what this task involves"? To give you some context, in our workplace we're quite friendly and not too formal with each other.

Answer 1

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 2

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.

Answer 3

I feel it's something people 50+ would be more likely to say. To me it means "experience", but at least one person in New Zealand who heard me use it thought I was referring to prostitution...