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I would recommend Prague for sure, honestly I wouldn't live anywhere else in Europe but in Prague. It's a lot of fun, very diverse with a lot going on, extremely vibrant and liberal and fairly easy to settle in and get a job.
So, since you speak Italian, why not go to Rome or Milano?
He seems to be looking for more exotic locales. The more exotic, the more un-boring. Italy would be too familiar. Russia should give him a run for his money.
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