Wayward Son’s 5 Sydney dates under $50


Single life often feels like you’re going on the same dates over and over again. Don’t despair my fun-loving Sydney-siders, we’ve got a list that will help you break that monotony without breaking the bank. Take a small risk (or a big one) and try something a little bit out of the ordinary.

Blue’s Point; Image Source: TimeOut 


Safe dates

Dinner and a movie? It’s a date staple, but let’s put a little spin on the classics and mix it up just enough to make it interesting. Here are two date ideas that are safe yet a little different.

The Apprentice Restaurant

TAFE might seem like a weird place to take a date, but The Apprentice Restaurant will make you forget your setting. Get served fancy gourmet dishes prepared by eager-to-please apprentice chefs. Don’t worry they’re under the supervision of their teachers so there is excellent quality control. What makes it interesting is that you never really know what you’re going to get when you walk through the door. Just make sure to make a booking because the place is always booked in advance.

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Ambience: Clean, dimly lit and set out like a proper restaurant, you’ll soon forget you’re at a TAFE.

Location: Conveniently located on Harris St in Ultimo, it’s very easy to get to and there’s street parking available in the surrounding streets.

Price: Lunch is only $25 per person for a three course meal. Dinner is $35 per person for a three course meal. Probably the cheapest gourmet meal you’ll find in Sydney.

Uniqueness: You don’t know who your chef is and what they’re going to prepare so the options are limitless. Plus, neither of you have probably been there before.

Romantic: Make sure to tell them that you’re going there for a date and they’ll turn the romantic levels up for you. They’ll seat you at a more secluded table and prepare flowers for your table before arriving.

Bonding Potential: With not many distractions and minimal potential for people-watching, you’ll be forced to talk. The meals are a good point of conversation and you tend to act like you’re food critics rating the apprentice’s work. However, if your date is a dud, this is a long haul dinner so probably best avoided for first dates!

Service: The service is phenomenal and they wait on you hand and foot, it’s the service you’d expect from a top tier restaurant.

Skyline Drive-In Blacktown

The movie date maybe cliché, but the drive-in hasn’t been a thing since the 50’s. It’s time you brought it back. Instead of heading down to your regular cinema, make the experience a little bit more memorable with a drive out west to Blacktown for a movie experience in the comfort of your own car.

Ambience: Technically this depends on your car, so make sure you clean up before you take a date out in your ride.

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Location: A bit out of the way being out at Blacktown, but it’s very easy to get to, just head straight down the M4.

Price: The best part is, it’s only $20 for the both of you, so it’s a lot cheaper than going to a regular cinema.

Uniqueness: When was the last time you went to a drive-in movie?

Romantic: The privacy of your own car is nice but things like your gearbox can be a bit of an obstacle. If you’ve got a 4wd, try reverse parking and making a little picnic area out back for the two of you. Cuddling potential maximised.

Bonding Potential: Unlike regular cinemas, you’re still able to talk without disturbing those around you – but be careful, your date may not want their movie interrupted.


A bit out of the box, these dates will require you to already have a bit of a bond to pull off properly. An  adventurous attitude is necessary.

Museum of Contemporary Art

This isn’t just for art lovers. In fact, it’s even more fun if you know absolutely nothing about art. Challenge your date, the premise is this – you both take turns touring each other around the exhibits. Relish in made-up explanations. Perhaps you may even find something that speaks to you.

Ambience: Being surrounded by beautiful artwork, you can’t really go wrong.

Location: Just a couple of minutes’ walk from Circular Quay, the location setting is as picturesque as the artwork.

Price: Free.

Uniqueness: Every trip to the MCA is unique, with changing exhibits and the way you see the artwork.

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Bonding Potential: Explaining artworks to each other will help you share your ideas and thoughts. You’ll open up and build a deeper connection with your date.

Blue’s Point

Grab your picnic rug and a warm cosy blanket and head over to Blue’s point for a romantic picnic. We recommend meeting up at a supermarket beforehand to make it a bit more fun. Set a budget and a time limit and raid the deli and cheese sections to build yourself a charcuterie board.

Ambience: What’s more romantic than majestic views of the harbour during sunset?

Location: Easily accessible by car or by the Darling Harbour Ferry (in fact, you can end your night with drinks there)

Price: All it’ll cost you is the price of the ferry (around $12 each – return) and whatever you’ve budgeted for food.

Uniqueness: Although the picnic sounds cliché, the location and food challenge at the supermarket is certainly unique.

Bonding Potential: The beautiful sunset views and the quiet setting will certainly set the mood, crack open a bottle of wine and enjoy the spoils of your charcuterie challenge with some great conversation.

Expert Mode

As the heading suggests, this is not for the faint of heart. Use caution, this is for those with a sense of adventure.

Dr Sketchy’s Anti Art School

To put it simply, it’s burlesque life drawing. You and your date will be drawing burlesque performers, vintage models and cabaret singers – expect some mild nudity. The event is hosted by MC’s that will get you involved and includes themed live performances. It’s a memorable experience that puts both of you right in the deep end. No need to be a competent artist, stuffing up is all part of the experience. This really puts the “likes trying new things” description to the test.

Ambience: A general air of just enough seediness to loosen things up

Location: In the basement of the Arthouse Hotel, an easy inner city location to get to.

Price: Entry is $25 per person including a sketch pad and a pencil. If you want to shell out a bit more, they do a dinner package with Arthouse Hotel for only $40 each.

Uniqueness: They don’t come more unique than this experience, this will have your date telling your friends all about it for weeks.

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Bonding Potential: Prepare to laugh a lot. From the entertainment to you and your date’s “masterpieces”, the whole night will be a blast. Bond over terrible drawings or get competitive over who would end the night with something that most resembles the subjects.

We hope that these will inspire you to think outside the box when it comes to your dates. As demonstrated, you don’t have to spend big to go on memorable dates. It’s all about the mindset and exploring the hidden gems of your city.

By Gian Reyes at Wayward Son

Got any other Sydney dates under $50 you’d recommend? Let us know in the comments below or join the conversation on FacebookTwitter & Instagram. And if you are ready to narrow down the world of possibilities, sign up to eharmony today- find someone made for you.

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