ThroughFriends
Surry Hills is where a lot of Sydney has its first dates and I do not think that is laziness. Everything worth going to is inside a twelve minute walk, the bars are small enough to feel warm and busy enough to be forgiving, and if the first place is not working there are four more on the same block.
This is not a list of the best bars around here, and a few genuinely great ones are missing from it. Being a great bar and being an easy place to meet someone you have never met turn out to be different things. These are the ten I keep coming back to for the second one, roughly in the order I would try them.
What I tend to notice
Mostly noise. Enough going on that a three second gap is nothing rather than an event, which I think does more work than anything else in this postcode.
After that, where you end up sitting. Bar stools seem to beat a two-top, and a two-top seems to beat a booth, which sounds backwards and I do not think is, because a booth quietly commits you to staying.
Then whether leaving after one drink would be a scene. And whether there is anything in the room to look at when you need somewhere for your eyes to go that is not directly at each other.
The ten
1. Golden Age Cinema and Bar, Commonwealth Street
Probably my favourite room in the city for this. You have a drink in the basement, which is dim and low and does an enormous amount of the atmosphere for you, and there is a film upstairs. Book it in advance and you have a two part evening with a natural change of scene halfway through. Do not book it and it is sitting there as the obvious next move if the drink is going well.
It manages to be flattering without being intimate, which I think is a hard trick. You can be nervous in it without feeling watched. The bar or one of the corner banquettes, and Poly is five minutes up the road afterwards.
2. Tio's Cerveceria, Foster Street
Small, red, no bookings, a wall of agave and no interest whatsoever in being taken seriously. It is loud, the crowd is friendly, and the staff will happily walk you both through something neither of you has heard of, which is fifteen minutes of conversation handed over for free.
I have watched two visibly nervous people turn into two people having a nice time in here faster than almost anywhere. You might well be standing. Midweek is best, and Dead Ringer is four minutes away when you want a seat.
3. Poly, Commonwealth Street
Tiled and dark and a bit sharp. Wine by the glass, snacks that turn up quickly, and enough of a crowd that nothing you say carries.
The reason it is this high for me is the bar seating along the side, which puts you shoulder to shoulder instead of eye to eye. It is a slightly dressed up room, so it suits a night where you both quite like the idea of having made an effort. Thursday is the night.
4. Dead Ringer, Bourke Street
A terrace with a courtyard out the back and staff who seem unusually good at spotting a table that needs a hand. The food is snacky, which matters more than it sounds, because you can eat enough to not be drinking on an empty stomach without either of you having agreed to dinner.
In warm weather the courtyard is the whole point. Loud, leafy, slightly hidden, and it turns one drink into a long evening without anyone deciding to. Vasco is six minutes away.
5. Vasco, Cleveland Street
Dim, red, rock and roll on, a plate of cheese and salami. It solves the awkward silence by making silence physically impossible, which is not subtle and does seem to work.
Probably better as a second stop than a first, though it does both, and it stays open late enough to be where a good night ends up rather than where it starts.
6. The Winery, Crown Street
Up the top of the hill, mostly outside, under the trees and the lights. It is the least cool place on this list and I will keep suggesting it anyway, because it is big and pretty and completely un-overhearable, and the staff have seen a thousand first dates and are kind about it.
It is also one of the only places around here that is just as good in daylight, which makes it my answer for a Saturday afternoon. Outside, always.
7. The Dolphin Hotel, Crown Street
Three quite different rooms in one building, a proper front bar, a dining room, and a wine room upstairs. What you are getting here is options. Start at the marble in the front bar, and if it is going well the night has an obvious next chapter twenty steps away, without either of you having to go back out on the street and rethink.
8. Bar Planet, Crown Street
Small, bright, unfussy, natural wine without the lecture. It is the sort of place where a drink can start at six and be finished by half seven with nobody's feelings hurt, which I think a first weeknight date should be allowed to do. Window seats, early in the week.
9. Shady Pines Saloon, Darlinghurst
Technically over the border and worth the two minutes. Down the stairs off Foster Lane, no windows, taxidermy everywhere, country music, whiskey. It is a stage set, and I think a stage set is a gift on a first date, because there are forty things in that room to talk about before either of you has to talk about yourselves.
The bar. Love, Tilly Devine is a minute away when you are ready to move.
10. Love, Tilly Devine, Crown Lane
A narrow wine bar up a laneway and one of the warmest small rooms in Sydney. It is more intimate than most of this list, which is why I think it is a better second drink than a first one. Once you already like each other, this is where you want to be. Upstairs if there is room.
If it is going well and you want to eat
The nice thing about starting with a drink is that dinner stays an idea rather than a commitment. Within a short walk there is Nomad on Foster Street if you feel like making a bit of an occasion of it, Longrain on Commonwealth Street with its big communal tables and a very good bar to wait at, Pellegrino 2000 on Bourke Street which is red and Italian and fun, and Nour on Crown Street if you want a table you will both remember.
Walk in and ask for the bar. Most of them hold seats back for exactly this.
During the day
A first date does not have to be at night, and I think daytime is underrated, especially if evenings feel like a lot.
Reuben Hills on Albion Street and then a walk to Prince Alfred Park. Single O on Reservoir Street for something quicker. Paramount Coffee Project on Commonwealth Street, which is easy to sit in for an hour without anyone hurrying you. Or The Winery again, on a Saturday.
Coffee has a natural hour built into it, which takes a lot of the pressure off, and it makes it very easy to say you would like to do this again properly.
A route, if you cannot face deciding
Poly at seven, Dead Ringer at half eight, Vasco at ten. Twelve minutes of walking all up, three completely different rooms, and each move is a small escalation neither of you has to say out loud.
A few practical things
Thursday, if you get the choice. Full enough to be warm, not so full you are shouting, and a weeknight has an ending built into it.
Most of the small bars here do not take bookings, which I have come to think is a feature rather than a problem, since no booking means no obligation. If you are worried about getting in, come at half six instead of half seven. Things fill up from about eight.
Central and Museum are both a short walk and the Crown Street buses run late, though neither of you should be driving to this anyway.
And it rains here far more than the postcards let on. Everything in the ten is indoors or under cover apart from The Winery, which is worth knowing on a grey Thursday.
None of this is complicated, which is sort of the point. There are ten warm and forgiving little rooms inside a twelve minute walk that will make an hour with a stranger easier than it would be almost anywhere else in the city.
If you have not got as far as naming a time, that is usually the actual problem. And if you want the rest of Sydney rather than just this postcode, it is over here.