This Whisky Dating Night Is The Way Sydney Singles Are Mingling IRL

If you’ve ever stared bleakly at your phone while debating whether “hey, how’s your week?” is worth sending for the fourth time, you’re not alone. Dating apps can become tedious, and we’ve forgotten the utter highs of locking eyes with a beautiful veterinarian-model-bookworm from across the bar.

To cure this online dating fatigue, Monkey Shoulder is taking over The Greenwood Hotel in October for a five-week residency called Monkey Shoulder House. The lineup covers everything from comedy nights and cinema sessions to dance floors and gloriously unhinged dating events. 

Plus,  Thursday and Monkey Shoulder are teaming up to flip the script on modern dating. Basically, if your love life needs a defibrillator, this is where it’s happening.

Instead of swiping through filtered photos, you’ll find consummate comedians hosting live matchmaking shows, anonymous ballot boxes collecting your funniest dating confessions, and a crowd that’s as ready to laugh as it is to love.

Pitch Your Mate

The first event of three will be taking place on Thursday 9 October, Pitch Your Mate. Bring your most single and love-lorn mate along, put them on stage, and convince a room full of strangers that they’re the total package.

It’s matchmaking via over-sharing, and it’s guaranteed to be seared into your memory bank until you’re holding hands with your forever person on a rickety rocking chair. 

But the hunt for love doesn’t stop there. The night also features a live dating show where four eligible bachelors try to win over one blindfolded person while the audience helps steer the chaos. Whether this goes to plan is an entirely different story and based solely on the good-natured onlookers. 

THE DETAILS

What: Pitch Your Single Friend
When: Thursday 9 October
Where: The Greenwood Hotel
Cost: $20
For more information, head here.

Sunday Funday

Sydney singles, consider your Sunday plans sorted. No swiping, no pressure—just good vibes, cocktails in hand, and real-life laughs with new faces. Ease into the afternoon with laid-back tunes, cheeky drinks, and a crowd that’s just here to meet, mingle, and maybe make a connection or two. Come for the conversations, stay for the laughs—and leave with a few new stories to tell.

THE DETAILS

What: Singles Sunday Funday
When: Sunday 26 October
Where: The Greenwood Hotel
Cost: From $20-$40
For more information, head here.

Happy Halloween

To honour the spooky season the crew are ending their singles series with a Halloween bash at Greenwood Hotel. Think flirty costumes, spooky vibes, and drinks that lift more than just your spirits. Ghosts, witches, or just here for a killer night out—everyone’s single, so get ready for some spooky sparks.

THE DETAILS

What: Singles Sunday Funday
When: Friday 31 October
Where: The Greenwood Hotel
Cost: From $20-$30
For more information, head here.

So if you’re single, semi-single, or just a fan of watching chaos unfold with a Ginger Monkey in hand, these whisky boasting dating events are your excuse to get off the apps and get back into the real world. Because honestly, humans were made for mixing in person. 

With plenty more mixing and mingling action taking place at the Monkey Shoulder House across the month of October, visit here for how you can get amongst. 

Editor's note: This article was produced in partnership with Suntory Bar. Thank you for supporting the partners who make Urban List possible. To read our editorial policy, click here.

Images: Urban List.