The Bamboozle Room

This is no ordinary burlesque show. The Night Cap Dinner Show at The Bamboozle Room in Kings Cross will give you and your loved one a taste of Roaring Twenties risqué vintage glamour, with choreographed dancing and live singing interspersed with stand-up comedy and circus. The package includes a two course meal, with shared entrees on intimate circular tables while you watch the show followed up with mains including pan-fried chicken, miso maple marinated salmon or a roast pumpkin bowl. This Gatsby-esque extravaganza is not to be missed: the doors open at 7pm and the show starts at 7:30pm sharp, ending at 9:30pm with an intermission for drinks and dinner. Make the most of the evening with a vintage cocktail from the fully-stocked bar and take in this night to remember together.

Photo credits:

  1. The Bamboozle Room
  2. The Bamboozle Room
  3. The Bamboozle Room

The Enmore Theatre

Tear your sides apart with this outrageously funny comedy special from Joel Creasey on his Messy Bitch Tour around Australia. At his one-night-only show at the Enmore Theatre, he’ll be offering up his trademark sass and unfiltered stories from a life in and out of the spotlight for you and your loved one to enjoy. Having previously headlined the Melbourne International Comedy Festival, New York International Fringe Festival and Edinburgh Fringe Festival, he’s sure to provide lightning-fast wit and satire that will leave you gasping for air. This is blue comedy at its absolute bluest; lewd, crude and unabashedly indecent. No kids are allowed as this is strictly an adults-only event with jokes to match.

Photo credits:

  1. The Enmore Theatre
  2. Live Nation
  3. Live Nation

Seymour Centre

It doesn’t matter if you and your loved one are muggles or master wizards; Potted Potter at the Seymour Centre will definitely put a laughing spell over both of you. Potted Potter was initially created by BBC television hosts Daniel Clarkson and Jefferson Turner as a live action skit to keep London shoppers entertained while they waited for copies of Harry Potter books at a signing event, but through positive reception it quickly developed into a smash hit international show. This Best Of Las Vegas 2019 award-winning comedy condenses the entirety of the seven Harry Potter books into a seventy minute satirical romp. You and your loved one can expect real-life Quidditch reenactments, ghastly makeup and plenty of throwbacks to the beloved series (or overrated tween drama, depending on who you ask- no obsession with the series is required to have a hilarious time). Sessions are available from 22 June to 4 July this year and are filling as quickly as a snitch so get in early and secure your spots.

Photo credits:

  1. Potted Potter
  2. Potted Potter
  3. Potted Potter

Hyde Park Barracks

Once the sun goes down, the school group tours are long gone and the party kicks off at Hyde Park Barracks in the CBD. We’re not talking about the bats in Hyde Park either. You and your loved one will be treated to live music and performances from a variety of acts curated by FBi Radio. Make the night count with a cocktail from the pop-up bar by Archie Rose, or enjoy food and drinks among some of the City’s oldest buildings. The After Dark nights run on Thursdays once a month throughout the year but book ahead to avoid disappointment.

Photo credits:

  1. Hyde Park Barracks
  2. Hyde Park Barracks
  3. What’s On Sydney

1989 Arcade Bar

Are you and your loved one serious gamers? Put all your niche gaming knowledge to the test at 1989 Arcade Bar’s ‘Game Over Man, Game Over!’ Trivia Nights in Newtown. Running on Tuesday nights twice a month, you and your loved one will have the chance to compete for a massive bar tab. The questions cover video games, movies and pop-culture and there’s an obligatory Arnold Schwarzenegger question every time.

Photo credits:

  1. 1989 Arcade Bar
  2. 1989 Arcade Bar
  3. 1989 Arcade Bar

The Running Joke

Enjoy three sets of back-to-back stand-up comedy at The Running Joke’s Triple Headline Fridays in Darlinghurst. You and your loved one will be treated to a triple slate of Australia’s most acclaimed comedians inside a former cabaret club. Mezze plates and cocktails are available delivered to your table so you don’t miss out on the laughs. Rated Sydney’s top comedy club on TripAdvisor, it’s the perfect date night experience for lovers of comedy who want to move beyond the usual Netflix stand-up recordings.

Photo credits:

  1. eventbrite
  2. eventbrite
  3. Tokyo Life

The Rocks Ghost Tours

For a spooky date-night experience, uncover the macabre history of Sydney with The Rocks Haunted Ghost Tours. Held nightly, the guides will take you and your loved one through some of the most cursed and haunted destinations in the city, visiting sites of misfortune and death that are still said to raise the hairs on your backs more than a century after they were first inhabited. Fell spirits still linger in the city after dark; previous guests have complained of hearing footsteps in long-abandoned houses, unusual cold spots in the peak of summer and inexplicable feelings of dread. Not for the easily frightened.

Photo credits:

  1. The Rocks Ghost Tours
  2. The Rocks Ghost Tours
  3. The Rocks Ghost Tours

The Comedy Store

Enjoy a handpicked lineup of the world’s funniest and most provocative acts with The Comedy Store Showcase in the Entertainment Quarter at Moore Park. In this 90 minute spectacle, you and your loved one will witness up to eight comedians deliver authentic stand-up comedy from Australia and around the world. It’s 18+ only, so expect plenty of mature content and adult themes for outrageous laughs. All tickets come with two complimentary drinks for you and your loved one to enjoy, delivered right to your table so you don’t miss out on the fun standing in line while someone in front of you has apparently never used a credit card before.

Photo credits:

  1. The Comedy Store
  2. The Comedy Store
  3. The Comedy Store

Mov’in Boat

If being stuck inside a dingy theatre isn’t your style, enjoy a movie night out on the harbour with your loved one at Mov’in Boat’s Floating Cinema in Darling Harbour. Choose from comfy cabana-style summer beds or a custom-built rowboat with padded seats so you can pick your favourite spot on the water. The films shown include recent blockbusters and old favourites so there’s definitely an option for even the most particular of tastes. Classic popcorn and movie snacks are available, but more discerning customers will enjoy the wide range of wines, beers and cocktails available at the licensed floating bar.

Photo credits:

  1. Movi’n Boat
  2. darlingharbour.com
  3. Movi’n Boat