"This year I didn't have a Valentine's Day date. So I ordered one online."

Guys… I did something weird. And I need to talk about it.

You see, the last three Valentine’s Days have been a running joke with my friends.

I am always alone. And I swear it always rains. And people around me are always receiving obnoxiously large bunches of flowers that semi hit me in the head as they get delivered.

I speak to Mia Freedman and Monique Bowley about purchasing my Valentine’s Day date online. Post continues below…

And everyone is always posting bizarrely intimate declarations of love on Facebook when really they should just be saying them to each other. In person.

To put it in perspective, my last Valentine’s Day card read “Hope you’re feeling better soon”, accompanied by a disgusting chocolate flavoured protein bar my friend definitely just found at the bottom of their gym bag as they pulled up to my house.

And the saddest part is…..that I ate it, because I was a little bit hungry.

Errr my last two valentine’s day cards ????????

A post shared by Jessie Stephens (@jessay1990) on

I’m 26 years old and haven’t been in a relationship for three years.

I feel the need to qualify that with “Oh – but I’m really happy”, and “I absolutely love my life”, which is true, but also completely irrelevant.


You can indeed live an extremely fulfilling life without a partner. But you can also be single, and sometimes, just a little bit, wish you weren’t.

About a month ago, I spoke on Mamamia Out Loud about feeling like somewhat of a feminist traitor.

I was the goddamn “modern woman” my ancestors fought for. I was satisfied in my career, surrounded by incredible friends, with a great relationship with my family. So why did I feel like something was missing?

Mia Freedman, Monique Bowley and I discuss the single status on Mamamia Out Loud. Post continues below.

So there and then I ‘confessed’. I was single and deep down I didn’t want to be anymore.

I wrote about how admitting you’re not altogether happy with your life is embarrassing.

It feels pathetic. If people knew I’d like to be in a relationship, but I haven’t been for the last three years, then maybe they’ll begin to wonder “… what’s wrong with her?”

My co-hosts, Monique Bowley and Mia Freedman, weren’t having any of this ‘woe is me’ bullshit.

So they set me some challenges. They uncovered some dating strategies and told me it was time to get out of my goddamn comfort zone.

And that’s how I ended up at an Italian restaurant on Valentine’s Day with a man I had ordered online.

Who had a Valentine’s Day card. Because I had definitely specified that I wanted one in the description.

EXCUSE ME. I got a card.

It was simultaneously the saddest, the weirdest, and the most bizarre thing I had ever done in my whole life.

It all began with an ad.

Over the weekend I posted a task on Airtasker, a Sydney based Australian company that "enables users to outsource everyday tasks".

Like finding Jessie a boyfriend, just for example.

It read as follows:

 I am a 26-year-old woman looking for a Valentine's Day date this Tuesday.

Conversational skills would be appreciated and also someone who enjoys dogs.

I am very nice, have stories, enjoy true crime but have never committed one, have a full time job and a doggo.

I'd prefer someone who has never been convicted of a violent crime, please.

This is an Osher Gunsberg approved activity.

A Valentine's Day card would be a bonus.

I'd like to go to dinner somewhere. Italian or Thai or Greek or Mexican.

Time: 7:30 - 8:30.

Age: 20-30 years old.

Doesn't smell bad. Doesn't judge someone who uses Airtasker to find a date.

I've attached a photo. Bios and photos welcome!



I am aware that my ad makes me sound:

A)  Like I'm 12 and a half.

B) Lonely AF.

and C) like I need some intensive therapy.

I feel like I left my dignity at the door when I signed up to Airtasker to find a boyfriend so, whatever. Haters gonna hate.

You may have also noticed that I forgot to specify what gender I'd like my date to be, which I discovered the hard way when nearly all of the applicants were single women who were really keen to catch up for a drink and bond.

As wonderful as that sounds, my project was to Airtasker a date, and that definitely would have been cheating.

So I amended my ad, and that's how I met Patrick T.

He replied:

Hi jessie

Am available tmrw.

26 years old. Smells great. Will be dressed appropriate and nice.

Def won't judge. Don't own a doggo. Haven't been convicted of a violent crime. Yet..

Had to google Osher.

Be driving in fully sick camry... but u get system aux.

how to not annoy all your single friends on Valentine's Day
What I imagined ^^^. Image via iStock.


He didn't attach a copy of his criminal record, but I trusted him nonetheless.

After some back and forth, and an intense meeting with my boss who felt like this definitely wouldn't fly with HR, I organised to meet Patrick at a nice Italian restaurant around the corner from work.

My conditions were: He had to pay for dinner with the money I paid him for the Airtasker date (feminism), he had to buy me a Valentine's Day card (romance), and I wasn't going to let him pick me up because, well, safety.

So last night, while my friends were having dinner, or intense sexy time, with their significant others, I was at a restaurant with an unusual fellow who I hired for one hour to talk to me.

He even gave me a stilted compliment at one point, which I believe was: "You're pretty". Aw. Thanks Patrick T!

We had a nice time, and talked about his love of the gym and interest in data entry, but somehow I don't think there is a future for Patrick and I. Mostly because Patrick was definitely, 100 per cent, there for the money. And I was definitely, 100 per cent, there because I was borderline forced to as an experiment for the podcast.

At one point, it did feel a little bit like I had hired a Valentine's Day escort. And that's just not a position I ever thought I'd be in.

I may not have found the love of my life in Patrick T, but I catapulted myself out of my comfort zone and broke the cycle of sitting at home with "Get Well" cards on Valentine's Day.

And with one date down, I'm that much closer to finding a REAL LIFE NOT PAID FOR Valentine for next year.

You can listen to the full episode of Mamamia Out Loud, here. 

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