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I Am Inspired By Kind People

Last night I was complaining to a friend about sleeping on a strangers couch in a city I've never been in before and how I've got to do it all over again today.

Then I woke up this morning and she'd sent me this..

[b]relevant!![/b] 😌
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Picklebobble · 56-60, M
I don't understand the last line.
What are you risking by playing it safe ?
And which of the two situations mentioned is supposed to be either ?