ThroughFriends
A mate rang me on a Wednesday last year, genuinely stressed about where to take someone the following night. I started saying "somewhere on Crown Street" and then found myself explaining why one particular place rather than another, and realised I had opinions about this I did not know I had.
So this is those, written down. It is not a list of the best bars in Sydney, and I am not the person to write that one. It is a list of places I have had good nights in, with a bit about why I think some rooms make meeting a stranger easier than others.
I should say up front that I am going off my own experience and the experience of people I have talked to about it, which is not a large sample and is not a science.
What I have noticed about the ones that work
The thing that surprised me most is how much of it is noise.
In a very quiet room, a three second gap is an event, and you both have to do something about it. In a room with a bit going on, three seconds is nothing, you have a sip of your drink and think of the next thing and nobody notices. I would not have guessed that mattered as much as it seems to.
The second thing is being able to leave. Not because anyone wants to, but because knowing you could seems to change how you turn up. A booked three course dinner is a two hour promise made by two people who have never heard each other's voice. A bar with stools and no reservation is a door left open, and as far as I can tell it is the open door that gets people staying till closing.
Third, having somewhere to go next. The best version of one of these is that neither of you wants it to end and there is an obvious next place five minutes up the road.
And last, something to look at. A bartender doing something daft with ice, an open kitchen, a bad painting, a dog under a table. Anything that lets one of you say a sentence that is not about your job. I think it is why walking beside someone is so much easier than sitting opposite them.
Surry Hills and Darlinghurst
Where most people end up, and I understand why. Everything is eight minutes from everything else, so a good night has somewhere to go and a flat one has an easy way out.
Golden Age Cinema and Bar
The bar underneath the old Paramount building on Commonwealth Street, and probably my favourite room in the city for this. You can have a drink downstairs and there is a film upstairs if you want one, and having that sitting in your back pocket takes a surprising amount of weight off the drink itself. It is dim and lovely and does a lot of the atmosphere for you.
Poly
Dark, tiled, a bit sharp. Wine by the glass without anyone making a ceremony of it. The thing I like about it here is the bar seating, because you end up side by side instead of staring at each other over a small table, and I think that changes a night more than it sounds like it should.
Dead Ringer
A terrace on Bourke Street with a courtyard out the back, and staff who seem properly good at spotting a table that needs a hand. The food is snacky, so you can eat a bit without the whole thing becoming dinner.
The Winery
Up the top of Crown Street, mostly outside under the trees. It is not the coolest place in this postcode and I am fond of it anyway. It is big and pretty and nothing you say can be overheard, and it is one of very few places around there that is just as good in the afternoon.
Vasco
Loud, dark, rock and roll on, cheese and salami. It fixes the awkward pause by making pauses impossible, which is not subtle, but I have never seen it fail. Good first, better second.
Tio's Cerveceria
Small, red, no bookings, a wall of tequila and mezcal and no interest at all in being taken seriously. Ask the staff for something neither of you has heard of and you have just been handed fifteen minutes of conversation you did not have to come up with.
I ended up with more to say about this area than fits here, so it got its own piece.
Newtown, Enmore and the Inner West
Cheaper, looser, much less like a performance. If either of you is worried about a first date feeling like a job interview, I would come here instead.
Earl's Juke Joint
King Street, barely a sign, almost always full. You will probably be standing, and I think standing is underrated for this. Easier to move, easier to lean in, easier to go.
Continental Deli
Martinis in tins and tinned fish and a running joke through the whole place. Good if you are worried about looking like you have tried too hard, because the venue has already decided not to.
Mary's
Burgers, metal, very dark. I have never seen anyone be self-conscious in Mary's, because you cannot hear yourself think, let alone worry about what you just said.
Young Henrys
The brewery in Newtown, drinking beside the tanks in the middle of an industrial block. No booking, and Enmore Road is right there afterwards. A Saturday afternoon is an underused format and this is a good place for it.
Bloodwood
If you actually want dinner but you want it to stay casual. Sit at the front, share a few things, and you have something to work out together in the first ten minutes, which I think is a gift.
The bowlos, Marrickville or Camperdown
Barefoot bowls is one of the great Sydney nights out and it costs almost nothing. You are side by side, you are moving around, you are both hopeless at it, and there is a reason to talk that is not the two of you. Book ahead in summer.
The city
Everyone writes the city off for this and I think that is exactly why it works. It empties out after six, so on a weeknight the small bars are full enough to be warm and not so full you are shouting.
Cantina OK
Four square metres in a service lane off Clarence Street, and one of my favourite rooms anywhere. There is nowhere to sit, so it is short unless you both decide otherwise, and I have come round to thinking of that as a good thing.
Ragazzi
Wine and pasta on Angel Place. Sit at the bar at the front. If you want to properly eat without committing to a booked table, this is how I would do it.
Old Mate's Place
Up several flights of stairs on Clarence Street to a rooftop and a couple of odd library-ish rooms. The climb is a small shared ordeal, which turns out to be a nice way to start a night.
Alberto's Lounge
Warm and red and Italian, and the staff are lovely to people who are obviously on a first date, which I do not think they get enough credit for.
Since I Left You
Down a lane off Kent Street, with a courtyard. A more relaxed crowd than the postcode suggests, and good on a Friday when the rest of town is a scrum.
Potts Point and Kings Cross
Ten minutes from the city and it feels like a different night entirely.
Franca
A proper bistro that will also happily just do you a drink at the bar. If things are going well this is where I would move to for the second hour.
Monopole
Dark and low and serious about wine without being snobby about it. Better with a bit of a crowd in, so Thursday or Friday over a quiet Tuesday.
Cho Cho San
Big, bright, open kitchen. You can talk at a normal volume without either of you performing, and there is always something happening in the kitchen to look at when you need a second.
Wendy's Secret Garden, Lavender Bay
Not a bar at all. A garden someone built into the hillside under the bridge, free, and one of the loveliest corners of this city. Coffee and a wander. Daylight only, and it rains here more than anyone admits, so it needs a backup.
Chippendale
Small and walkable and full of things to look at, which I think makes it good for anyone who finds sitting still on a first date hard work.
White Rabbit Gallery
Four floors of contemporary Chinese art, free, with a tea house downstairs. Galleries are the old reliable for this and I think it is because you are side by side, there is a constant supply of things to have an opinion about, and neither of you is carrying the conversation alone.
Spice Alley
Outside, cheap, busy, hawker style. Low stakes, and Kensington Street is right there when you want to move on.
Freda's
Rougher and later than the rest of this, usually with something on. Better as a second stop than a first, I reckon.
Bondi and the east
Worth the trip in the warmer half of the year, and honestly a bit of a mission on a Tuesday in July.
The Bondi to Bronte walk
The walk is the whole thing. Twenty five minutes each way, side by side, the ocean doing the heavy lifting, and no bill until you both decide there should be one. Late afternoon, and let it turn into a drink if it wants to.
North Bondi Fish
Big windows, the beach in front of you, loud in a friendly way. I think lunch here is much better than dinner here.
Speedos Cafe
The daytime version. Coffee, eggs, the quiet end of the beach, and a natural hour built into it.
The lower north shore
The Oaks, Neutral Bay
Enormous and old and full of people on a Thursday. What it gives up in intimacy it makes back in ease. Nobody is watching you, and there are five rooms at five different volumes, so you can just move if the one you are in is not working.
The Manly ferry
Half an hour on the water for an Opal tap, which I think is the best value of anything in this city. You get a view to talk about instead of each other, and arriving somewhere together seems to make two strangers feel like a pair much faster than meeting at a bar door does.
If you are not drinking
I did not want this to be a footnote, because a lot of people I know are not drinking at the moment and most of the usual suggestions quietly assume everyone is.
- Coffee and a walk. Room 10 in Potts Point and then the Elizabeth Bay foreshore. Or Reuben Hills in Surry Hills and then Prince Alfred Park.
- Bouldering. BlocHaus in Marrickville, or the climbing gym at St Peters. You will both be terrible, which is most of the appeal.
- The Art Gallery of New South Wales. Free, enormous, and there is a proper walk between the two buildings now.
- Gelato and a wander. Messina, or Cow and the Moon in Enmore. Ten dollars and forty minutes and no obligation. Also a very good rescue plan when a coffee is going better than either of you expected.
- Carriageworks markets on a Saturday. Busy, cheap, side by side, done inside an hour.
- Mini golf, or the arcade. Silly on purpose. Having something to do with your hands seems to take a lot of pressure out of the first half hour.
The ones I would probably avoid
Dinner, on a first one. Two hours facing each other with a bill at the end that has to be negotiated. It is a lovely third date.
A gig or a film as the entire evening, where three hours go by without either of you learning much. A film after a drink is great. A film instead of a drink feels a bit like avoiding the date.
Anywhere silent and expensive, where every pause is amplified and the bill hands you a second thing to be anxious about.
And your own local, which I have done and would not do again. If it goes badly you have lost a pub, and if it goes well you are explaining who that was to the bartender for six months.
A few things people ask me
How long should it be? I would aim for about ninety minutes, though I am not sure anyone should be timing it. Long enough to get past the CV bit, short enough that nobody is hunting for an exit. If it runs to four hours, wonderful, but I would let that be a decision made on the night.
Who pays? Whoever did the asking offers, properly and without a performance. The other person offers to split, once. Then it is done. Small bills make this a non-event, which is another reason I lean towards a drink over dinner.
Weeknight or weekend? Weeknight, personally. Calmer rooms, easier tables, and a Tuesday has an ending built into it. Thursday seems to be the sweet spot here, it feels like the weekend and it still has a bedtime.
What if I run out of things to say? I do not think you will, but I know the worry is real, and the only useful thing I have is to pick a room where a pause costs you nothing. Although honestly, most of that particular fear seems to belong to the fortnight of texting beforehand rather than to the night itself, which is a different problem.
Meet there or meet first? There, I think. Either of you can be five minutes late without it being a thing, and the first moment you see each other happens in a room with other people in it rather than on an empty footpath.
I have almost certainly left off your favourite, and Sydney being Sydney a couple of these will have changed hands by the time you read it.
But the specific list matters less to me than the thing underneath it, which is that there are hundreds of warm, loud, forgiving little rooms in this city, and most of us are using about four of them.