Nail That Crucial Third Date with These Memorable Date Night Spots in the CBD

For a lively spot that blends history and flavour with a joyous mariachi band, look no further than this converted printing press turned two-storey Mexican restaurant. Indulge in traditional delicacies with a modern twist, from al pastor tacos to yellowfin tuna ceviche.

The bar and restaurant offers an extensive spirits collection — it claims to be home to the largest collection of mezcal and tequila in Australia. The space takes inspiration from the underground basement bars of Mexico City and the building’s art deco history with preserved heritage aspects and a floor-to-ceiling mural. With its intimate ambience and culinary delights, Esteban is sure to impress your date, especially if they love tequila and mezcal.

Image: Steven Woodburn

If your date is a country music fanatic, your third date should take place at Jolene’s. This Nashville-inspired bar has booths named after famous country stars, so you could spend your night in the Chris Stapleton, Johnny Cash or country music star and icon Dolly Parton booth.

There are more than 150 different whiskies in its collection, including 100 sourced from American whiskey distillers. Or, opt for one of the exciting cocktails — the Love Story, featuring Bombay Gin, watermelon, lime and mint, seems fitting for the occasion. Pair with the venue’s southern fare boneless buffalo bites, Nashville sandwiches and pulled pork loaded tater tots.

But what you’re really here for is the live music. Local country and rock musicians perform on Thursday to Saturday from 8–11pm, so you and your new person can get the country music spirit flowing.

Treat your date to a more refined experience by heading to the hatted restaurant Kuro Bar and Dining. Here, high-quality Australian produce and native ingredients are treated with traditional Japanese techniques.  

Chef Teramoto previously worked at Michelin-starred Restaurant Pages, Paris and Florilège, Tokyo. He draws on this culinary experience and his Japanese heritage to create the venue’s signature dishes, best enjoyed with a drop from the 200-plus-strong wine list courtesy of sommelier Wanaka Teramoto. The focus is on boutique, minimal-intervention Australian producers.

There are also Japanese beers and an extensive range of premium Japanese spirits, sake and umeshu (Japanese plum wine) on offer. You can elevate your date night even further with the cocktail omakase experience — the first of its kind in Sydney. Sit at the bar and enjoy a carefully curated selection of cocktails, expertly paired with delectable snacks from the kitchen.

Japanese touches can be found all over the venue, from the chandeliers to the kintsugi-inspired gold flakes in the concrete floor’s cracks, making it the perfect venue to broach the idea of a couples’ trip to Japan (too soon?). Planning a daytime date instead? Kuro’s sister venue Kahii is mere steps away.

We’ve suggested Japan, and now we’re (symbolically) heading to the other side of the planet: Great Britain. Those brave enough to mosey down a darkened alleyway off Clarence Street in search of a stiff drink will be rewarded. The unassuming courtyard is home to this 1800s-style British tavern, somewhere Charles Dickens might have penned Great Expectations over a couple of ales and a pork pie.

It’s a cosy spot with a fireplace and moreish food options from a Sunday roast (available daily) to a classic fish buttie sandwich. If your date is a Pom yearning for home or has recently returned from the quintessential Aussie sojourn to the UK, this hidden tavern will have them transferring all those warm affections onto you. Snuggle up by the fireplace with a pint and feel like you’re stepping back in time.

Image: Kitti Gould

It’s date three and you’re both a little obsessed with each other. This laneway locale, lit by soft lamps and natural light from the large streetside window, is a great place to make googly eyes over the table while sampling from an outrageous collection of mezcal.

Dinner time offers contemporary Oaxacan deliciousness via an extensive a la carte menu. There’s a raw bar offering ceviche and fresh oysters, five types of taco, four iterations of traditional moles and a range of share plates, including lamb shoulder barbacoa, smoked duck breast and charred prawns. There are also two set menus if you and your new special someone want to avoid making decisions and instead focus on making your way through the six margarita styles.

It’s normal for things to still be a little awkward on date three. Cut through the tension by hitting up this new subterranean bar by the Door Knock team, which has a regular rotation of live music, DJs and themed nights to keep things interesting. The venue is majestically decked out with plush floral seating and wallpaper adorned with ferns, so whimsical you’ll soon forget you’re underground in the busiest part of Sydney.

The venue boasts a solid cocktail and wine offering across its two drinks lists — aptly named ‘Now’ and ‘Then’. The snack menu features dishes like the panko-crumbed ham hock croquettes, lobster and prawn vol-au-vents, devilled eggs with black bean salsa and pomme dauphine with smoked trout. There are also daily specials for only $12.

Image: Natalie Ng

Underneath The Charles Grand Brasserie and Bar, you’ll find TIVA, a sophisticated lounge bar that made our list of Sydney’s most romantic venues. Head down Wednesday through Saturday to find a roster of curated nights, which includes ‘DJs and Bao’s’ on Wednesdays, Mixer Thursdays, TIVA Fridays and Reve Saturdays.

Once you’ve found your table or booth, your attention can turn to what you’ll pair the night’s playlist with — think wasabi margaritas, mandarin gimlets or lemongrass cosmos.

If you want to pull out all the stops, ask for TIVA’s extensive champagne list.

As for food, TIVA takes cues from its upstairs sibling by serving a French-inspired pan-Asian array of eats created by executive chef Billy Hannigan. The menu features showstoppers such as the stuffed chicken wing with prawn, spanner crab and ginger and mini confit duck spring rolls with a spicy sauce made using the same technique as its sister venue, The Charles’, famous duck a la presse.

If your third date is going really well — so well, in fact, that you want to make it last even longer — we know a place you should check out. The Little National Hotel Sydney is everything you want in a city hotel: compact, luxurious and overflowing with amenities including a luxe rooftop terrace. While away the rest of your evening in front of the large open fireplace with a delicious cocktail in hand or make your way to one of the stylish guest suites.