Bars & Pubs

The Single Guy’s Guide to First Dates in Sydney

By Daniel Colasimone
11th Sep 2014

Chaps always talk about how good it is to be single, but 87% of the time they are actually lying.

Sure, going to bars and clubs with your mates and hitting on women sounds like a blast. More often than not, though, those nights end with you alone in the line at Maccas and result in hellacious hangovers and a pillow that's soaked with the salty man-tears of despair and defeat.

The chances of meeting a lady you genuinely like are slim. The chances of ending up at an ear-drum-burstingly loud club wall-to-wall with dudes, spending all your rent money, embarrassing your friends, and waking up to the taste of kebab-with-tabouli-and-garlic-sauce in your mouth are high.

Let's face it. Unless you have the looks of Michael Fassbender or the charisma of Larry Emdur, girls are most likely to be repelled by your gawkish attempts at pitching woo.

Unless you're mega-rich like Mitt Romney, or have a glamourous profession like 'Urban List writer', you are going to have to spend a huge amount of time and effort just to convince some random mademoiselle that you are even worth talking to, let alone going on a date with.

But say you actually meet a nice girl, perhaps at Book Club or in your life drawing class, and she agrees to go out with you? The whole dating thing can be a bit of a chore, too. That sounds very cynical. It can also be joyous and life-affirming. But it can also be a chore. If you realise early on that there is no spark between the two of you, the whole situation can get plain awkward. If only there were some magical third party that could come in and sort out your date night, and your friends could come too, and they'd shout you a round of drinks. Oh wait, there is – Winger. Don't know it? You should. It's bloody awesome.

Anyway, back to this girl you met in rehab. You want to take her out somewhere fairly casual for a first date, without the pressure of the whole fancy dinner-and-a-show thing. You still want to impress her, though.

Here are a handful of locales in Sydney that hit just the right tone for a first date.

Baxter Inn | CBD

If you'd like to take your special lady to a saloon that reflects both your virile masculinity and effortless class, take her to Baxter Inn. One of the city's trendiest bars oozes so much charisma that some of it is sure to rub off on you. You can't help but come across pretty damn smooth when they're playing the blues and you're holding a single malt whisky. 

Bondi Hardware | Bondi

A funky bar located within skipping distance of the beach, Bondi Hardware boasts a heap of awesome menu options and some tasty drinks, too. These guys have made a splash on the Bondi scene despite only having been around for about three years, and it is easy to see why punters are drawn to the place. As a first date spot, it is relaxed and inviting.

The Winery | Surry Hills

This uber chic Surry Hills bar sets the right mood for a romantic encounter with its sultry ambiance. As the name suggests, the wine list is extensive and prices are more than reasonable. The dining options are not too shabby either, and it always seems to be full of attractive Sydneysiders. Depending on how good looking you are yourself, you can take that as a positive or negative.

The Crow Bar | Crows Nest

A bar with super-friendly staff who really know their stuff is always going to be a great date destination, and Crow Bar certainly fits that bill. Grab some tapas and let the guys guide your drink selections as you sit back and enjoy the conversation in this stylish little Crows Nest locale.

The Commons | Darlinghurst

This place really does tick all the boxes. The atmosphere is warm and intimate (whether you opt for indoor or outdoor seating), the menu is uncomplicated but perfect and the Downtown bar has a Jazz Age-inspired charm that should have your date cooing her approval. 

Mojo Record Bar | CBD

Into music? What better place for a meet up than Mojo Record Bar, which is spattered with thousands of vinyls, dozens of classic posters, and a million talking points? This former record store is more than just a concept, though. The range of craft beers is impressive and the cocktails are very well made, indeed.

The Botanist | Kirribilli

'Cosy' is the first word that comes to mind to describe this Kirribilli cubby house, and while botanist, Gerard Fothergill might seem a strange thing to theme a bar after, somehow it just works. When you understand that the man himself studied spices and herbs that could be used in cooking, the concept becomes a little clearer. Shared plates and share cocktails make The Botanist perfect for groups, so if you're on a Winger, you're all set. Oh, and don't leave without trying the Juniper Tea Party cocktail.

Need help in the dating department?

Speaking of dating… need some help in that department? Think I should be punched in the nose for suggesting all these great places when you still CAN'T GET A DATE to actually take to them? Well, what if I told you we could organise a great night out for you and two of your mates, match you up with three cute chicks, and send you to one of the best bars in town? You'd be keen, right? And we haven't even told you that we're shouting the first round. Girls + drinks + more girls + mates + fun. Why are you still reading this? Click on over to Winger and register for one epic party.  


Image credit: Warner Bros. The Winery

Get our top stories direct to your inbox.

Unilever tracking pixel

You May Also Like