No one is saying first dates are easy – there’s the reasonable fear you might insult them, bore them or that they may turn out to be secret racists. And it’s worse still if you think you might like them – so many expectations to manage. Do yourself a favour and pick a location for that first meeting that matches your vibe, be it low key and local or a litmus test for how they feel about the things you love best – namely wine.
Continental Deli Bar Bistro
It can be the little flourishes that make somewhere a great date spot. This fully licensed delicatessen is the sort of place where they’ll present you with a tray of beautiful French tins of sardines so you can choose your flavour. They’ll also put your Martini in a tin, which means it arrives chilled and perfectly dilute, ready to be poured into a glass. 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.
This Must Be The Place
One of the rookie errors you can make on a date is accidentally getting a bit wastey pants. And it’s easy to do, especially if you’re drinking through the awkward silences. That’s why you want to make tracks to this light and bright Darlinghurst cocktail bar where they specialise in lower alcohol concoctions that do not compromise on taste. They’ve got a rockstar bar team here so don’t be afraid to order adventurously off the Spritz menu, but for a guaranteed crowd-pleaser you want the Gloss, made with fresh strawberries, citrus vodka, watermelon infused Riesling and rosewater. It sounds super sweet but is fresh and restrained.
This lauded wine bar and restaurant is a great place for a low-lit tryst. You can sit up at the bar, order amazing wines by the glass and perhaps a beautiful, earthy steak tartare and pretend you’re in a Parisian noir film. And if it all goes pear-shaped it’s only a short jaunt to the station or to a second venue to meet a friend and decipher where it all went so wrong.
A fairly large swathe of Sydney works in and around the CBD so if you’re both in the city at 5pm, it makes sense to grab a drink nearby and save everyone unnecessary travel time. Happily there is a slick new ’40s-themed cocktail bar right in the heart of the financial district. Get in right after work or hang back a bit for your best shot at two empty seats and then order up rum cocktails to break the ice. They even provide entertainment in the form of the bar’s business card, which is actually a little paper plane you can pop out and assemble yourself.
You know what, 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. The hip hop lyrics printed over 15th Century frescoes are also great talking points, and if things are going really well you might even opt for a late supper of extra cheesy baked eggplant and the tender house ragu.
Since I Left You
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 place is a hidden gem where you can order carafes of house wine, crostini and after-work Spritzes and feel like you’re miles away from the CBD.
Did you know that a photograph of the cocktails at this inner city bar was turned into a print used by Romance was Born in a recent runway show? 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? These are all fun facts to impress your date with when you take them to this monochrome bar tucked down a laneway off King Street.
Beaches make great date spots. They are good for active people who want to body surf, paddle board and play volleyball, and they are also good for the sloth-like crowd who prefer basking in the sun. But come dusk you need a second destination and Neighbourhood is the place to go post-Bondi bathing. It’s casual so you won’t need two outfits; they know the romantic capabilities of a bottle of rosé; and the menu features date-friendly fare like burgers and toasties – no pesto here, folks.
A pub is a good entry-level date spot. There’s always a crowd so you have pack-safety (just in case they’re more Freddy Krueger than Freddie Prinze Jr); it’s a relaxed venue so the pressure is off to dress up or spend big; and they’re full of good distractions if conversation falters. In addition to televised sport (perhaps you’re both Swans fans?), at the Erko you’ve also got a jukebox and pool tables to play with. Plus the dinner menu covers all your bases: devoted carnivores can go HAM on the smoked meats menu and vegos are all sorted with the juicy mushroom burger.
This bar is a great shout for anyone who doesn’t like being crowded into a space where people can hear your conversations – you’re working hard at being charming and you don’t need an audience. Lock down a set of the luxurious metallic velour armchairs that are spaced a comfortable distance from other seats and provide good personal space for you too. They keep the music low here so you don’t have to yell or repeat yourself, and table service means you don’t need to interrupt your flow to get another drink or order up some high-end sushi if things are going well.
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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.