Paddington Pleasures 

Paddington is a suburb where the saying there’s a pub on every corner is actually a reality. Crammed full of amazing places to get a drink, picking a favourite pub in Paddington is like asking the Date Knight to pick a favourite child…..

Luckily, (touch wood!) the Date Knight has parented zero kids (that I know about). So, moving right along. The heat is now on to deliver the perfect pub to start this hard-hitting date suggestion.

Rooftop Drink @ The Light Brigade in Paddington

Thanks to recent renovations, The Light Brigade now boasts one of the best rooftops in Sydney. It’s 83 metres above sea level to be precise!

If the sun is shining, you are in for a real treat. The Light Brigade has Frosé available! Yes, you read that correctly. If you don’t trust yourself around the delicious pink nectar of the gods (last Saturday’s drinking intervention springs to mind), enjoy a Pimm’s Jug as your eyes devour the spectacular view of Sydney, and hopefully the spectacular view of your date!

If you are feeling especially peckish and need to eat before the next venue, share a wood-fired pizza.

Dinner @ The Wine Library in Paddington 

Drinking wine in the library. That thought will take you back to a better time and place when you were in University…. Not! No one actually drinks in the library, that doesn’t make sense. If you did, I’m glad we weren’t friends.

Luckily, you can drink at The Wine Library without judgement. This venue is an elite date location. With quality comes cost, so skip your second coffee all this week and treat yourself to a Charcuterie & Amigos instead. Don’t know what that means? Neither do I, but I think it’s Italian for deliciousness.

As the name suggests, there is an excellent range of wine available. Over 500 wines, with the majority of these coming from Italy and France. Don’t let the choice scare you off. Just pretend to know something about wine and then order the second most expensive bottle like you always do. Bon temps!

Drink @ The Phoenix Woollahra or Woollahra Hotel In Woollahra

The end of this date is like a choose your own adventure book. The Date Knight has been so kind to provide two options for an end of dinner drinky-poo.

The Phoenix has a range of cocktails that will ensure you wake up at least 25% more hungover than you had planned. The aptly named Phoenix Rising is a cocktail that celebrates the venue’s charm or throwback back to the year Y2K and order the Greek Island Ice Tea.

Alternatively, the Woollahra Hotel terrace has you covered on all occasions, with a rooftop ideal to enjoy a warm evening or a fireplace to enjoy a before-bed glass of red on a cold night (go for the Xanadu Cabernet Sauvignon).


Recommended days: Any night of the week

Total date cost: Approx $160 total

Romantic rating: 4.5/5

Spiciness rating: 2/5


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