Nobody ever said first dates are easy. Our advice? Pick a place where the cocktails are excellent, the food is good, and the service is outstanding. Why not factor in great views, drag shows, show-stopping drinks or standout locations while you're at it? That way, if all goes well, things can only get better. And if it doesn't...well, it's time to move on.
Did you also know that in addition to excellent drinks, these guys also make their own line of sodas, including a smoked lemonade that they make by putting a tray of ice cubes in the smoker at LP’s Quality Meats? This is a fun fact to impress your date with when you take them to this monochrome bar tucked down a laneway off King Street.
Not only does this neighbourhood boozer serve up vegetarian and vegan-friendly dishes, but the list of beer, wine and cocktails also happens to nail it. Come before or after a movie at the cinema down the road if you wish, or make this fun-loving spot the main event for the night.
Whether it’s the taxidermy, the caravan in the back courtyard, the gender-neutral toilets or the great weekly queer performances, there are plenty of first date ice breakers at this colourful Regent Street bar.
There are more than half a dozen wines by-the-bottle for under $60 at this all-class European-inflected wine bar on Llankelly Place, so you can work your way through a bottle or two along with some buffalo mozzarella, slow roasted pumpkin or cured kingfish.
This Oxford Street cocktail haunt offers attentive (but never overbearing) service, interesting drinks (they're playing with an apocalyptic theme ATM), low lights and minimal noise (there's a great backing soundtrack, but it's never 'What-are-you-saying' loud).
Order up a maple pecan Old Fashioned at this subterranean bar that channels Old Hollywood glamour without an air of pretentiousness. Check out what's screening in the cinema if you want to catch a film while you're at it.
This walk-in wine bar is all about interesting vinos curated by sommelier Julien Dromgool and tasty snacks by Ester's Matt Lindsay. It's as good as his five star Chippo resto, but a bit more casual, making it excellent date night territory.
This airy Pitt Street bar will shake you up a great cocktail, and it's intimate enough to feel special, but not so fancy that it feels OTT for a first date.
The pleasures here are as sophisticated and grown-up as they come: a serious wine list, housemade charcuterie, an ace selection of cheeses, and a menu of more elaborate share plates if things go well. Bonus for points for the sexiest lighting in the city.
If your date's a flop you'll be more than entertained by the nightly drag show, and if it's a success the dancefloor downstairs will serve well as your next destination.
Marrickville is lucky to have this little wine bar, which is home to one of the best natural-leaning wine lists in town. Very friendly staff and very comfy furniture come in very handy, so don't feel like you need to be the one making all the right moves.
Fire! Plastic dinosaurs! Rum! All these drawcards make this bar a novel spot for a first date. The couches are comfy, the interiors are spiffy and many of the cocktails are a spectacle in their own right.
If you take someone here for an afternoon of old-fashioned cocktails, soft cheese and freshly sliced charcuterie and they’re not into it, that person probably isn’t for you.
It’s really hard to take things too seriously if your drink is blue, or full of crème de menthe, or packed with purple liquorice and shaded by a tiny umbrella. That’s the beauty of a drink at Big Poppa’s; they have the skills to master the classics and then get a bit silly with the drinks list.
There’s no denying we live in a really ridiculously good looking city, and this glass-boxed rooftop bar makes the most of our good looks with 360-degree views of the harbour. It's also indoor and outdoor, so even if the weather's average, you can still take in the views.
Bondi has a bunch of great restaurants and average backpacker bars, but not many wine bars. Ode is the remedy to this problem, offering up natural wines and generous plates of pasta in an intimate setting.
Yes, there are toasties. Yes, there are craft beers. And yes, there is a fair bit of everything in between. This is one of Marrickville's best local watering holes, which makes it an easy option should you want to take it slow, grab a couple of drinks and get to know each other.
Keep things real casual at this ol' Chippo boozer. There's deep dish pizzas and plenty of beer on tap to aid your first date nerves, and things kick over into dancefloor mode later on if you feel like a sneaky DF smooch.
We don’t need to tell you how much Sydney loves a rooftop bar, so impress your date at the top floor addition to the East Village Hotel (previously the Darlo Village), which is an A-grade, lofty drinking perch.
We don’t know about you, but we like a little retro-romance on date night, which is exactly why we’re into the idea of sharing a fancy toastie on a candle-lit table out in the enclosed laneway of this inner city bar.
This Pyrmont wine bar has hosted plenty of first dates within in its sandstone walls. It's a stone's throw from the city, but doesn't have the crowds most city bars have, making it a good option for your first date.
Feel like heading somewhere a little more local for your first date? This low-key bar is located in the leafy Lane Cove, and makes for an ideal first date spot for anyone living on the Lower North Shore.
They say half the adventure is getting there, so put that saying to the test and catch a ferry to this sun drenched harbourside pub as a warm-up for your drinks and dinner date.
Need a new date?
These modern-day cupids are doing things the old-fashioned way – face-to-face! We've profiled the best matchmakers in Sydney to find out how they got started, their biggest success stories and what they think of online dating. Plus, we've got a list of upcoming speed dating nights and our top picks for first date bars.