The Playmaker
Let's play
  • It's Friday
    What day is it?
  • Now
    What time is it?
  • Anywhere in Sydney
    Where are you?
  • What do you feel like?
    What do you feel like?
  • And what else?
    And what else?

Neighbourhood Bars and Pubs That Are Perfect Third-Date Territory

Step it up a notch with live music, experimental cocktails and late-night eats.
By Concrete Playground
August 28, 2020
By Concrete Playground
August 28, 2020


in partnership with

Step it up a notch with live music, experimental cocktails and late-night eats.

You've passed the nervous jitters of the first date, and you're feeling good after a follow up rendez-vous, so now what? When you're planning a third date, you'll want to get a few things right. First up, the venue should be easy-going and inviting. You're still getting to know your potential future partner, so it's wise to choose a place that's not too loud or raucous, making it easier to chat. At the same time, you want to be somewhere fun and interesting.

Whether you're after a rooftop bar with killer views, a place to eat with an impressive wine list, or a lesser-known neighbourhood gem with live music, we've teamed up with American Express to bring you this list of places that'll guarantee your catch-up has the right vibe and provides some talking points. Settle in for an evening of people watching, live performances or plates of delicious snacks, all with your Amex Card in hand.

  • 9
    Jangling Jack's

    Potts Point is well known for its prestigious restaurants, but did you know it also has a killer cocktail bar? You’ll find this cool-as haunt on Victoria Street, where the team is shaking up classic cocktails like aviations, martinis, or the bar’s signature banana daiquiri. If a negroni is more your speed, you’ll want to head in from 4–6pm when they’re just $10. You can head here for a late-night date, as the kitchen stays open well after 9pm — there’s romance to be found in steak frites at midnight. When you’re in third-date land, you can talk the night away — and this is the perfect place to do that.

    Image: Diana Scalfati

    READ MORE Add to Playlist
    Want to start building your ultimate playlist?

    Start creating a personalised itinerary — or add to an existing list. Save it, share it and take it with you on your next local adventure.

  • 8
    Nick & Nora's

    Parramatta’s very own glitzy cocktail bar has old-world glamour down pat. The bar pulls out all the stops, from liquid nitrogen-fuelled martinis to a brass telescope propped up on the balcony. That balcony really makes the most of its 26-floor location, too, with panoramic views across western Sydney to the Blue Mountains and the city skyline. With its impressive bells and whistles, this bar is a good location when you’re out to impress a certain someone. And you don’t have to worry about a taxi bill home if you live in Parramatta or its surrounds.

    Image: Jiwon Kim

    READ MORE Add to Playlist
  • 7
    Bulletin Place - CLOSED

    Begin your adventure by winding stairs up to this elegant Circular Quay cocktail den. Its ever-changing roster of cocktails is dreamt up by BP’s gun bar team, led by owner Tim Philips-Johansson, who took home the gong for World’s Best Bartender back in 2012 and has been scoring accolades and industry respect ever since. Order one of the left-of-centre tipples, which change almost daily and feature inventive riffs on the classics. Add in excellent service and a cheeseboard and you’ve got an ideal date night in our books.

    Image: Cesar Echeverri

    READ MORE Add to Playlist
  • 6

    Excellent vino can make a date that little bit better, and Fix Wine Bar knows a heck of a lot about fine wine. It has been in the game since 2006, and this great little bar comes without the usual pretentiousness of a run-of-the-mill wine den. So whether you’re a vino buff or just want to explore some different options, its super-friendly staff make this spot an ideal place to bring someone you want to get to know better. Staff will help you to work your way through the 38-page wine list without judgement or snobbery. If you’re both working in the CBD, its city location and European-leaning menu also makes it the perfect afterwork spot for a weeknight date and a bite to eat.

    READ MORE Add to Playlist
  • 5
    Golden Age Cinema and Bar

    Going to the movies may have been suitable date night material when you were a teenager (and, honestly, we still love a night at the cinema), but now you’re a little older and wiser, it’s time to step things up from a trip to the multiplex. Golden Age Cinema & Bar is where you’ll get cutting edge cinema programming alongside a slick cocktail bar offering. You can even order drinks to be delivered to your cinema seat midway through the film. Housed within the heritage-listed Paramount Building, the cinema itself only seats 56 people, so it’s a more intimate way to catch a film. The bar, which you can visit whether or not you’re going to a screening, does an ace highball and toasties. Of course, there’s plenty of popcorn to share, too.

    Image: Cassandra Hannagan

    READ MORE Add to Playlist
  • 4
    The East Sydney Hotel

    This corner boozer has probably seen more dates and poured more pints than any other bar in Sydney; it’s been serving cold ones since opening in 1856. It’s a classic pub — there’s darts to entertain yourselves, a cosy vibe in the front bar, and an open fireplace when you want to snuggle up. The place has plenty of character, and Sunday is the day to pop in as there’s live jazz music to liven up the mood. For now, Sunday jazz evenings require bookings in advance and tickets cost $10 a head, but we think it’s a small price to pay for a memorable evening at the pub.

    Image: Cassandra Hannagan

    READ MORE Add to Playlist
  • 3

    This intimate Redfern bar may specialise in gin, but it’ll show you a great time no matter your choice of spirit. Swing by on Tuesday or Sunday nights to make the most of the bar’s free live jazz performances. You’ll hear sultry sounds of the Squares — a Sydney four-piece bebop jazz outfit that plays renditions of jazz greats like Miles Davis, Charlie Parker and Thelonious Monk. The bar also does $10 negronis on Sunday night to help you see out the weekend in style.

    Image: Steven Woodburn

    READ MORE Add to Playlist
  • 2
    Peg Leg Tavern

    Pyrmont has never been known for its hopping bar scene, but that’s half of what makes Peg Leg so fun. This surreptitious pirate-themed bar is big on fun, whether you’re after a blue-hued tropical cocktail, a tiki drink served in a skull, or just a tin of craft beer. The party-shirt sporting staff will be sure to pull out all the stops to make your third-date a breeze. Also, this is a good spot for vegans and pescatarians, with plenty of plant-based and seafood options on the food menu, to go with your colourful drinks.

    Image: Cassandra Hannagan

    READ MORE Add to Playlist
  • 1
    The Crow Bar

    On the north shore, this easy going date spot is an excellent place to step up your date nights. On Sundays, it has live music, which will add the perfect soundtrack to your evening out. Its extensive menu makes it a crowd-pleasing dining option, too. Opt to share tapas-style plates of chorizo, zucchini frites, chicken wings, oven-baked haloumi and wild mushroom risotto balls. Or if you’re not quite in sharing territory yet, go for the pie of the day or a beef burger.

    Image: Cassandra Hannagan

    READ MORE BOOK A TABLE Add to Playlist

Support the places you love and shop small at the local stores that make Sydney so great. To learn about American Express, its Shop Small initiative and current Shop Small offer, which ends on August 31, visit here. Then, head this way to find more must-visit spots.

Top image: Cassandra Hannagan

  •   shares
Tap and select Add to Home Screen to access Concrete Playground easily next time. x
Counter Pixel