'When do I pull the pin on this?' Isabelle Silbery on the brutal reality of dating after divorce.

This is an edited extract from Out of the Box by Isabelle, Emmie and Kerry Silbery, published by Simon & Schuster Australia. It is available in stores nationally and online. You can purchase a copy here.

When Mum told me she was going to do 'web dating', first, I corrected her: 'It's called online dating'; and second, I told her (in probably an insensitive way) that she was too old to date.

I know that may have seemed harsh, but my protective instincts had gone into overdrive. If I'm honest, I was feeling scared that maybe Mum wasn't equipped to enter into the jungle of the online dating scene.

The jungle was all too familiar to me. Two years in, and it was still the harsh, unexpectedly hurtful and ridiculously funny adult playground it had always been. Not only was I in my mid-30s and a divorcee, but I was also a single mum - there's no doubt some men would have seen 'needy' flags before they got to know me. 

But I was in no need of a saviour, money machine or sugar daddy. I was looking for someone I could enjoy life with on my days off from being a mum.                      

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I know people bang on about silver linings but, as soul-destroying it is to be apart from your own child, it frees up time to discover... men. I didn't mention Lulu [my son] until well into a proper face-to-face date, and I never used any images of him online. I'm too aware of the dark side of the internet and, going by the look of what I was swiping past, there's no way I was going to be preyed on for my little boy.

But it was time-consuming. I mean, some nights my thumb got sore, there were that many 'f**k noes'.

And don't get me started on the never-ending text messages. I am busy. I am getting dinner ready and bathing my kid. I can't be bothered telling you about my day, or ogling over your topless pics. Just pick a day and let's meet up properly. We can chat then, bye.


The first match was water-skier Tim. All the guys I meet have a name like this on my phone. It's also how I refer to them when debriefing with my friends.

He was tall, mid-20s, tanned and confident. He was returning from the States as a world champion water-skier. I was nervous. I hadn't been on a proper date for more than eight years.

But it was surprisingly quite easy. 

Wine and conversation flowed, and I instantly felt safe in his arms when he hugged me goodbye.

When I got home, I rang my bestie. She was telling me to play it cool. She demanded I send her pics immediately, so, while she was talking, I took screenshots of all his Tinder pics and sent them to her. 'Babe, they haven't come through yet.' Oh f**k. 'Oh, my God. I just sent them to him.'

This clearly didn't stop him from liking me, because we ended up having an on-and-off long-distance 'thing' for a few years. I grew to like him, too, but when he said, 'I just want to get married to someone for the first time and have kids of my own,' I got it. 

As harsh as that was to hear, I totally got him and his honesty. It reassured me that if I was to ever commit to a man, he would need to be someone pretty special, who loves all of me and what comes with it.

The next match was Crazy Tim. Two Tims in a row. 

We had a drink at a bar to iron out the risk that he wasn't normal. I'd stalked him on ALL of the things. LinkedIn; looked good; Facebook; yes, he had friends and family. All seemed well.


These were all things I was going to have to teach Mum.

Tim was in his late 30s, and also divorced and with kids. Bingo, I thought. Someone who gets it. Our third date was at his house, which was next level. His house was immaculate, beautifully styled, everything in its place. Kids' toys neatly put away, and every cushion indented with a karate hand-chop like in the magazines. 

We sat sophisticatedly at his candle-lit dining table, where he rolled out the most amazing home-cooked three-course meal. He poured me a wine but said he didn't drink. I didn't care. I was in dating heaven. 

Sitting up in his bed and being brought the chocolate mousse he'd made earlier was exactly what the doctor ordered. If this was what dating was like, I thought, I had sifted through the d**kheads to find a d**k attached to a man who really knew how to treat a woman.

But the next time I went over to Tim's, everything seemed a little off. 

He answered the door looking completely dishevelled - shirt was unbuttoned, hair a mess, and music pumping.

Unusual for a Thursday evening at 5pm. My eyes scanned the room as I walked in, trying to piece it together while making small talk. Kids' dirty clothes were all over the floor; the kitchen looked like a bomb had gone off. 

I sat down at his bench and Tim proceeded to make me 'the best sodka voda' he'd ever made. I was perplexed until my eyes caught sight of an empty bottle of red wine. Just as I realised he was a big drunken mess, he turned around with the biggest kitchen knife I'd ever seen.

Oh Jesus, I said to myself.

At what point do I pull the pin on this? While singing along to Ed Sheeran, who was blasting on his stereo, he attempted to cut a lime in half, which was clearly wanting to escape him as much as I was. I ended up putting him to bed and an end to us. 


For a few weeks afterwards, I did do a few drive-bys after dropping my son off in the same street. I got to understand the likes of Tim's dating game. Monday, there was a silver VW in his driveway. Tuesday, an Audi Q5. Thursday, I texted him, saying, 'Hope she enjoys the chocolate mousse.'

I am pretty thick-skinned but, at the same time, these experiences pricked me inside like a small sharp pin. I didn't want my own mother - who'd been through enough - to go through any disappointments. I didn't want her to question herself or her worth, or be taken advantage of, or be faced with the likes of a Crazy Tim with a knife.

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I went on countless dates after that. 

Men who didn't look like their pics, men who didn't have much to say, and men who vomited their whole life story to me as though I was their therapist. But the lovely men were the worst. Lovely, interesting and attractive enough men, who I kissed on the cheek saying goodbye. 

And in the Uber, tipsy from drinking myself into trying to find a spark, I was overcome by a deep sense of emptiness. Pins pricking me right where loneliness lives. Feeling I'm alone in this world. Looking at the lit-up city outside my window, couples walking hand in hand, tears would flow. I wondered if my driver ever noticed and thought I was a weirdo.

'Do you mind if we stop by drive-through Maccas? Thanks...'

My life was split between two Isabelles.

One Isabelle was single, carefree, and confident. I took the time to look and feel good. To laugh and stay up all night. To be adventurous, curious, and sometimes stupidly risky. 

But then, there was Isabelle, the mother. I had no time for myself. My priority was making sure Lulu was okay. I rarely washed my hair, was permanently in activewear and in bed by 9pm, after reading many stories and lying with him until he was asleep. On those nights, dating was the last thing on my mind. Lulu was my primal focus. He was an infantile plant that needed lots of water, sunlight, and care while he was with me. 

I wondered, was I ever going to let anyone see the two sides of me? Would anyone love me, both as the woman I am, and always have been, but also as a mother? When the father of your own child doesn't, it's only natural that I questioned it.

Although at times, dating was exciting and exhilarating, and gave my married friends hours of entertainment, it does get harder as you get older and have a lot more to lose. That's why I wanted to protect Mum, because whoever she let into the life she had built for herself had to be very special. 


Maybe it's different when your kids are grown up, but I knew I was just going to have fun until the right man came along, who deserved to see me in all my glory. But even when it felt exhausting, I reminded myself, no one is a waste of time. 

Unless it's an uninvited d**k pic - then it's an immediate delete, block, goodbye.

This is an edited extract from Out of the Box by Isabelle, Emmie, Kerry Silbery, published by Simon & Schuster Australia. It is available in stores nationally and online. You can purchase a copy here.

You can follow Isabelle on her Instagram here.

Feature Image: Instagram @isabellesilbery.

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