Sydney’s beloved rum bar Old Love’s is set for a major expansion, with owner Dre Walters revealing plans to transform the neighbouring former Since I Left You site into a larger venue complete with a New York-inspired courtyard bar, and significantly increased capacity.
The project, which quietly begun trading last week, will almost triple the venue’s capacity from its current 40-44 guests to around 120 once complete.
Walters said the opportunity came after taking over the former Since I Left You premises, which sits directly behind Old Love’s and connects via a rear laneway.
“We’ve taken over the space that used to be Since I Left You, which backed onto Old Love’s,” Walters said. “We have a back door that opens into the alleyway and through to our bar. Originally it was only used to take rubbish out, but in hindsight it became the catalyst for why we took over the space.”
The expansion has not been without its challenges. Shortly after work began, scaffolding was erected by a neighbouring building that shares the laneway, temporarily limiting plans for the outdoor area.
“It’s a slow project because we share the alleyway with the neighbouring building, who conveniently started putting scaffolding up once we took over,” Walters said.
“There’s nothing we can do apart from wait, but we’re happy to play the long game because we really love the space. The vision we have for it will be something quite unique. I don’t really know of anything else like it.”
Rather than delay opening entirely, the team has opted to trade while renovations continue, with improvements being rolled out week by week.
“We opened earlier last week and there was no scaffolding. The next day there was scaffolding. Last week the courtyard lights got an upgrade, next week the toilets get some love, so every week something new is getting added,” Walters said.
“It’s quite fun trying to trade while getting it all done at the same time. When we took over the lease there wasn’t a rent-free period, so you have to keep ticking over.”
Once complete, the centrepiece of the expansion will be a landscaped outdoor courtyard inspired by a memorable visit Walters made to New York City.
“The courtyard is designed to be a New York-style oasis in the city,” he said.
“The last time I was in New York I stumbled across this alleyway bar that felt like a jungle, surrounded by old brick walls and fire escapes. It just felt like you were somewhere else, and that really stuck with me.”
“Aussies love drinking outside, so it’s going to be a great addition to Old Love’s.”
The redevelopment will also see the former Since I Left You indoor bar refurbished into a premium function and activation space, including a dedicated rum room designed to mirror the aesthetic that has made Old Love’s a favourite among Sydney’s rum lovers.
“The grand plan is to put another bar in the courtyard along with a small upgraded kitchen once the scaffolding is gone,” Walters said.
“We’re also renovating the Since I Left You bar space so we can use it as a higher-end functions and activation space. We’ll be adding a little rum room that matches the décor and feel of Old Love’s itself.”
For now, the outdoor area remains unavailable for private bookings as construction continues.
“You can’t book out the courtyard yet because every week it’s changing little by little,” Walters said. “But the place will take shape.”
While still very much a work in progress, the expansion marks a significant next chapter for Old Love’s, allowing the award-winning small bar to grow without losing the intimate character that has defined it since opening. With its blend of indoor and outdoor spaces, dedicated events offering and ambitious design, the project is set to create one of Sydney’s most distinctive rum destinations once complete.