Be careful after dark around Central Station, which is where the vast Sydney Central YHA (youth hostel) is.
Also be EXTREMELY careful in Redfern at night. It can't be stressed enough. Don't go there unless you have a specific reason to. Scan each street BEFORE you start to walk down it. If you see unsavoury people milling about, assess whether it looks/feels safe.
(Redfern isn't any prettier by day, but at night it is very unpleasant.)
Also watch out for drink-spiking. If you begin to feel unusual after someone has bought you a drink, TELL THE BAR STAFF. Don't worry about phoning your silly friends to save your ass, etc, just TELL THE BAR STAFF that you need help.
I have been in Sydney all my life. I love it even though I live in the bad parts and I'm usually around after midnight. (I work until late then go to bars.)
Be cautious around Central Station and its immediate surroundings - including Surry Hills, Belmore Park, Prince Alfred Park, Cleveland Street, Waterloo and Glebe. (Glebe has trendy cafes and a day-time culture, but it also has seedy parts.)
Another popular place for revellers is Woolloomooloo Bay, a dockland area that has lively pubs and even some expensive restaurants. However, it also has a housing estate ('projects') that are dangerous. There are transient people and petty criminals in these areas and it's just a block or two away from the posh restaurants and friendly pubs.
Some Sydney parks can also be risky after dark: for example, The Domain, Prince Alfred Park and Belmore Park, all in the city centre. The latter two are very near Central Station.
Other areas that experience occasional night-time dramas are William Street, Kings Cross and Oxford Street, plus the dark side-streets that border them.
Always keep your wits about you. If drinking, remember that booze can lower your decision-making skills, your alert-ness, risk-assessment, etc.
Australia has an informal drinking culture, but fights can break out when people drink too much, so watch out for hot-heads, too.
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