Nobody ever said first dates are easy. Our advice? Pick a place where vibe is king and ace cocktails, first-rate snacks and excellent service are all talking points, too. Why not factor in great views, drag shows or standout locations while you're at it? That way, if all goes well, things can only get better. And if they don't, well, it's time to move on – and you can't say you didn't give it a red-hot go.
Where to bend the elbow and break the ice...
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.
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.
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.
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.
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.
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.
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 giant Buddha's head, the hi-res waterfall mural, or the all-out lost-in-the-jungle atmospherics, there's plenty to feast your eyes on at Saga Bar. Bottom line: you definitely won't be short of things to talk about here.
When you pull up to the Cove Deli, just off the Corso in Manly, your plus-one might have some questions. When you open the upcycled vintage fridge door at the back and descend the spiral staircase into Sydney's snazziest speakeasy, you'll prove you have the answers.
The thought of Paris in the 1920s conjures plenty of romance, and Merivale channels it elegantly and imaginatively at this petite cocktail parlour in the Ivy complex. The lights are low, the drinks are stiff and the mood is just right.
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.
There's no need to worry about anything at Earl's. The natural wine selection is just as good as the range of craft beers, and they're both on par with the excellent cocktails. Now for the hard part: a seat up at the bar, against the wall or a table in the back?
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.
The journey down the stairs and through the winding corridor is a perfect way to settle all those butterflies. Once you've finally reached this cosy little cubby – which feels further underground than Town Hall Station – grab a well-deserved cocktail, find a poky corner and get acquainted.
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.
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.
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.
One of Sydney's OG small bars is still one of the smallest, which makes this self-appointed "retro-sexual" haven an optimal spot for a party of two. Pro tip: the signature peanut butter colada is an epic cocktail to finish the night with.
Feeling comfortable goes a long way when it comes to a successful maiden outing, and what's more comfortable than a few pints of lager in Arcadia's world of upcylced timber furniture, exposed brick, fairy lights and framed vintage cross-stitch? This is unpretentiousness at its peak.
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.
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.
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.
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.
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.