My friend Harry spends his Saturday nights at the busy end of Melbourne’s romantic streets, looking for love and the perfect date. Sadly, he’s yet to find it. It’s not his intentions that leave him unlucky in love – they are honourable. It’s more the idea that the perfect date even exists, and the implicit pressure. Like some in relationships like to say, ‘If it’s meant to be, it doesn’t matter where you go on your first date.’

Well, we disagree. We think thousands of potentially happy couples have stumbled in their infancy because one of them comes to the depressing realisation that they don’t want to spend their life in mundane restaurants with the same person. Sometimes a date just doesn’t work. Other times though, finding a place that inspires the both of you and creates the right mood, can kick-start the perfect romance, both parties wandering home thinking, ‘I could get used to this’.

A first date should be casual and somewhere you’re going to feel comfortable, so we’ve put together our list of Melbourne’s most suitable date spots, which includes places we might just be regulars at anyway.

DRINK
Having a drink is a good way to ease into the date in a relaxed frame of mind. If you’re really nervous, you can go somewhere that’s busy and make observations about the after-workers. If you want to have a quite chat you can find a booth at one of Melbourne’s hidden bars and settle amid the ambience.

City Wine Shop
Our top pick for a relaxed drink is City Wine Shop, from the owners of The European and the Supper Club. This understated, low-key wine bar nestled at the top of Spring Street is around the corner from so many great city restaurants, and is open all day, early morning or late at night, for a date at almost any hour.

Gerald's Bar
Another Broadsheet favourite is Gerald’s Bar in North Carlton. Owner Gerald Diffey’s staff know the wine list back-to-front and the jovial atmosphere quickly calms the dating nerves. If you’re lucky, they’ll open a bottle just for you and even put on a record upon request. It’s quite romantic really.

Cicciolina’s Back Bar
Cicciolina is a favourite for the St Kilda crowd, who flood in every night for delicious Italian food. The dimly lit back bar has the same qualities – a cosmopolitan transit lounge for the people waiting for a table in the front, or just passing time in a booth over a negroni and olives.

Joe's Shoe Store
Joe’s Shoe Store is a rousing date spot on the crest of Rucker’s Hill in Northcote. Joe’s is dark, cosy and comfortable – in other words, the ideal place for two to tuck in for the night. And if you find yourself lobbing on Joe’s doorstep around dinnertime, be sure to order a pizza that can be delivered from Pizza Meine Liebe next door.

Long Play
Long Play is part of a growing scene in North Fitzroy, alongside quality establishments like Supermaxi and Jorg. The minimalist interior is interesting enough to kick off the conversation before strolling out the back to watch a movie in the full screen cinema. Cross the road Supermaxi for dinner afterwards, or for something more casual, a burger at Danny’s.

Honourable Mentions:

The Alderman – cosy drink after dinner
Gertrude St Enoteca – glass of wine
The Everleigh - cocktails

EAT
Eating involves a little more risk than drinking, with split bills, pasta sauce and white shirts. That said, food brings people together and there’s nothing more enjoyable than eating with someone you love or want to get to know.

Ladro – Gertrude
If you’re filling up on pizza, it needs to be at a cosy restaurant, with a good wine list. Ladro is both, and more. Those Italians just know how to romance.

Il Solito Posto
Il Solito Posto is another one of those Italian restaurants that Melburnians love to cuddle up in. The lighting is low, the wine list is sophisticated and the food is delicious. You’ll soon be eating spaghetti from the same bowl like Lady and the Tramp.

Golden Fields
We’ve got a lot of love for Andrew McConnell’s newest southern venue. Inspired by his time in the kitchens of Asia, the food is fantastic and you can rave about it for hours, so conversation is not a problem.

Mamasita
If the name isn’t enough, Mamasita (meaning ‘hot babe’) serves tacos and tequila until late at night. The food is fresh and simple, made using seasonal produce. A match made in heaven.

Umberto Espresso Bar
This tiny espresso bar in Thornbury is steeped in heart-warming family tradition. Umberto’s owner Marco Finanzio named the place after his father, who is often there helping serving traditional Italian dishes, coffee and wine. The tiny size and casual style makes it a most romantic restaurant.

I Carusi
Our second pizzeria on the list, we think sharing is always a good ideas for dates. This relaxed pizzeria prides itself on turning out the very best of simple pizzas, served quick, crisp and fragrant with quality toppings. The only trouble is choosing which ones. The swift service makes it ideal if the conversation goes awry.

Chin Chin
There are no bookings at Chin Chin, so it’s a wise choice if you want to keep things low key and spontaneous. The food has spice and zing and the wait staff are young and vibrant. We recommend sitting on the bar stools, watching the chefs in the kitchen.

MoVida Next Door
The younger sister of Movida, Movida Next Door epitomises Melbourne’s food and wine culture. It’s all hustle and bustle here as you watch chefs shuck your oysters right in from of you. Tapas means you’re sharing, which is a good start. Order sherry to wash it down and your off on a good wicket already.

Honourable Mentions:
Il Bacaro
Claypots
The European
France Soir

OUTSIDE
When you go for a date outside, you take out most of the stress. There is no reaching for the wallet, or worry that you’ve ordered the wrong thing. You can watch the city turn from day to night, or find a quiet spot for a picnic.

Prahran Market/Botanic Gardens
The Prahran Market is full of delights for daters. You can do laps on the stroll, pick out your favourite produce and head to the Botanic Gardens for a picnic.

The Observatory at the Botanic Gardens.
There is a tour of the Observatory every Monday night in summer at the Botanic Gardens from 9pm to 10.30pm. You can see Jupiter and most of its moons, as well as Uranus and Neptune. It’s a nice opportunity to see the stars, and the gardens at night.

Hooked
Head to Hooked in Windsor and then straight down to Elwood beach to watch the sunset. Like the outdoors and fish and chips on the beach, the offerings at Hooked are hard to beat and you’ll be reeling her (or him) in.

Moroccan Soup Bar
The vegetarian menu at Moroccan Soup Bar makes you look thoughtful. There is nothing worse than making an awkward assumption early in the piece. Take in a takeaway container and get them to fill it up for you to take over to Edinburgh Gardens for a picnic.

Rooftop Cinema
We’re not convinced a movie is the best idea for a first date; the whole point is to enjoy your date’s company. But for an iconic view over Melbourne, visit the rooftop bar at Curtin house on a warm night. The location is pretty impressive in itself, so the movie can be a fallback option if conversation wanes, or something great is on.

Food Trucks
There are so many of these cropping up these days. From the Beatbox Kitchen and Taco Truck to Gumbo Kitchen and Le Sausage, there’s a food truck around almost every corner up north. Head there early and nab a spot on the grass to enjoy a balmy night.

Bicycles
Pedal around and discover the city you live in by bike. If you don’t have your own, you could pick up a Melbourne Bike, then ride off into the sunset. A bike trip is downright romantic and always rewarding. Nothing beats that first drink after a cross-town bike adventure. Be sure to lock up your bikes together.