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FOOD & DRINK

Sydney's Least Awkward Spots for a First Date

Because first dates are nail-biting enough without the added challenge of picking a good place.
By Yelena Bidé
November 10, 2020
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By Yelena Bidé
November 10, 2020
  shares

SYDNEY'S LEAST AWKWARD SPOTS FOR A FIRST DATE

in partnership with

Because first dates are nail-biting enough without the added challenge of picking a good place.

We've all been there. The flirting has been successful and you've locked in a first date (score!), but the excitement about your upcoming encounter is quickly dampened by the stress of deciding where to go. And as anyone who's ever been on a first date knows, picking the right spot for that initial rendezvous ain't easy. You want somewhere with good drinks and buzzy vibes but where the getting-to-know-you chats aren't going to be drowned out by the music. And that's just the beginning of the requirements. Long story short, there's a lot to consider and, while our fair city is filled with great bars and restaurants, they're not all created equal when it comes to being solid first date material.

Because first dates are nail-biting enough without the added challenge of picking a good place, we've partnered with American Express to round up seven spots that are perfect for that initial encounter. These places are all casually trendy, not too loud but also not awkwardly quiet, and with stand-out drinks and food offerings to fuel the evening. Plus, they all accept Amex so you can stock up on some extra points. Browse the list, pick a place and spend the rest of that pre-date time choosing a killer outfit and brushing up on those scintillating conversation skills.

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    This Kent Street gem has all the trappings of a great first date spot: a central location, outdoor seating, regular live music and an attractive cocktail list. Grab your date and head out into the lively urban courtyard decked out with a huge mural, twinkly lights and hanging plants. Despite the excellent live music (expect soul, funk or hip hop beats depending on the night), SILY is still somewhere you can hold a proper conversation without having to shout. Order a few drinks — the Shirazzle Dazzle is particularly good — to help the conversation along and, if things are going well, extend the evening by ordering one or two of the moreish toasties.

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  • 5

    Hidden up a flight of stairs on Oxford Street, Bitter Phew is the place to go when you want to treat your date to an insanely diverse range of beer. The drinks list is 300-plus names strong and includes everything from stouts to sours, along with a 12-strong craft beer tap rotation. While the drinks are fantastic, we’re especially in love with this spot for its collection of board games, because there are few things that take the pressure off a first date better than some friendly competition.

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  • 4
    Archie Rose (Sydney) — Shortlisted for Best Australia and Pacific Bar 2015

    Save this one for a first rendezvous that seems especially promising, because the glory that is the Archie Rose Distilling Co. is not to be wasted on a meh date. Sydney’s first commercial distillery in 160 years, this Rosebery locale is both an operating distillery and an adjoining bar. Before settling into one of the bar’s barrel-inspired booths, impress your new flame with a tour of the distillery, where you’ll learn how the gins, whiskies and vodkas you’ll be imbibing later are produced. For $30 a head, you’ll get a tour of the space, followed by a tasting of their core spirits. Once you’ve decided on your fave, head into the bar — with its stunning old-world fit-out — to get some more of the good stuff, paired with a range of bar snacks and sharing platters.

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  • 3

    Tucked away on a sliver of Manly’s Market Lane, Donny’s works the industrial warehouse chic vibe to the fullest with exposed brick walls, lofty ceilings and glass bottle light fixtures. Start your date with drinks on the ground floor (the rich Hibiscus Chilli Margarita is a firm favourite) and then, if things are going well, make your way up the spiral staircase to the foodie heaven on the second level. Expect uber-fresh ingredients, impeccable presentation and incredible seafood. Happy hour runs three nights a week, while Wednesdays offer the date-friendly special of half-price meals.

    Top image: Katje Ford.

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  • 2

    If it’s a classy first date you’re after, make your way over to CBD fave, Kittyhawk. Slip into one of the green leather booths along with the rest of the post-work crowd and get ready to imbibe some old-world luxury vibes. This bar — with the very niche theme of ‘the Liberation of Paris on August 25, 1944’ — serves up custom cocktails and French bistro fare so good they deserve a medal. With bar food at the very top of its game, there’s gruyere cheese doughnuts, braised beef short rib, and bone marrow toast with XO sauce. Meanwhile, the cocktails are all about the rum and rye. Don’t miss the Last Post, blending shaved dark chocolate, Wild Turkey bourbon, and a date and peanut butter syrup. And though it would be a shame not to sample at least a few of the excellent cocktails on offer here, if it’s wine you’re after, the lengthy list of Aussie, French and Italian drops will not disappoint.

    Kittyhawk is currently closed until further restrictions are lifted.

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  • 1

    For a first date venue that feels more like sitting in the living room of a vibrant share house than a bar, The Bearded Tit is your best bet. With its warm, arty vibes — fruit chandeliers, a taxidermy warthog playing the trumpet and framed portraits of Jesus in the bathrooms are just the beginning — this is a spot where colourful characters flock in droves. Hook yourselves up with a few classic cocktails from some of Sydney’s friendliest bartenders, and then settle down at one of the wooden booths for what’s guaranteed to be a good night. While the in-house food offerings are somewhat limited, when hunger hits you can order in from nearby Wah Fung or Lorentto Pizza. The Bearded Tit also puts on a range of live shows that’ll provide ample material for you and your date to chitchat about.

    The Bearded Tit is currently closed until further restrictions are lifted.

    Image: Katje Ford.

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FYI, this story includes some affiliate links. These don’t influence any of our recommendations or content, but they may make us a small commission. For more info, see Concrete Playground’s editorial policy.

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