*Names have been changed for anonymity purposes*
It comes as no surprise that my friend Jennifer’s* ill-fated relationship began with a classic enemies-to-lovers trope.
“I thought he was very arrogant,” she tells me over drinks one night. “But we definitely had the hots for each other.”
They were both in relationships at the time, and nothing happened for more than a year. When they finally got together, he was 21, and she was 23.
Jennifer didn’t know it then, but the eventual end of that relationship wouldn’t just mean losing the man she thought she’d marry. It would force her to confront something far harder: why she’d spent so much of her life believing that being chosen by a man was proof she was doing life right.
A strong start
“We moved in together after five months of dating,” she recalled. “Then, two years later, I got offered my dream job in New York.”
Ryan had a choice: move with her or end the relationship. He chose her, and off they went.
“He was super close to his family, starting out his own career and just loved the Aussie lifestyle,” she told me. “But not coming meant breaking up.”
He chose her, and off to New York they went.
Despite being just 24 and 26 by this time, Jennifer and her beau started toying with the idea of getting married.
“Looking back I think we were crazy,” she laughed. “But at the time we felt so ready for it.”
They even booked the wedding before Ryan had even proposed!
The official proposal eventually came during a boat ride in Central Park.
“I just thought he was getting gum out of his pocket,” she said. “So I continued whatever childish joke about semen I was making.” Classic.
“Aside from that it was all very lovely,” she laughed. “And in that moment I genuinely did want to spend the rest of my life with him.”
Cracks in the facade
“My friends and family never really liked him,” Jennifer admitted. “He was overprotective and envious of how deep our connections were.”
To make matters worse, Jennifer’s career had her flying first class around the world and paying for everything, while Ryan struggled to establish himself in New York.
“That would be hard for a man of 40, let alone a guy of 23.”
While trying to deal with Ryan’s bruised ego, Jennifer was also fighting her own mental battle: imposter syndrome.
“I was really self-destructive,” she said. “I didn’t feel like I deserved the life I had so I just got blackout drunk all the time.”
She got stuck in a cycle of medicated highs and lows: doing cocaine all weekend and then coming home and popping benzos to unwind.
“I don’t know how I didn’t die,” she confessed.
Homeward bound
Mirroring the stability of their relationship, the the 2008 financial crisis left Ryan with no chance of getting a job in New York and a strong desire to return home.
“So I gave up the dream job,” she recalled.
Arriving home a few months before Jennifer, Ryan was given one important task: find an apartment that she could buy for them to live in.
“I was going to pay for it, but he kept dragging his feet,” she said. “We ended up living in his parents’ pool house.” A move that, she assures me, had none of the quirky charm of Ryan Atwood’s story on The O.C.
“We were fighting more, I was drinking more, he kept going out and not coming home,” she said. “It was a disaster.”
Yet the engagement party still went ahead, and you can take a guess how that went…
“We had a huge fight,” she said. “Partly thanks to his speech, which was beyond embarrassing, especially in front of my family.”
According to Jennifer, he said something along the lines of: “May all of our ups and downs be in the bedroom.”
Stop the wedding
Following the disastrous engagement party, Jennifer decided they needed a fresh start and to finally leave the parents’ pool house.
“He wouldn’t move out, so I left on my own,” she said. “I was still wearing the ring but we were basically not together anymore.”
The engagement ended soon afterwards, beginning two years of breaking up and getting back together. They even planned a romantic trip to New Zealand for her 30th birthday, where Jennifer was told another proposal was coming.
They never made it.
“We broke up for the last time and I moved back to New York.”
Unlike the story portrayed in Ashe’s viral song Stop the Wedding, Jennifer’s broken engagement left her feeling like a “failure.”
“I used to liken it to being an artist,” she explained. “It felt like spending years painting the most incredible picture and then waking up to find your canvas is blank again.”
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No man, no worth
Growing up in a time when women were conditioned to believe that if you didn’t have a man by your side, you had nothing and were nothing, made Jennifer feel even worse.
For women who came of age in the ’90s and early 2000s, the message was clear: being coupled up meant you had succeeded. Rom-com heroines spent two hours finding their soulmate, magazines taught us how to get him and keep him, and being single was often treated as a temporary state you were supposed to be actively trying to escape.
So when Jennifer’s engagement ended, she wasn’t just grieving Ryan. She felt as though she had lost the life she was supposed to have — and, worse, that everyone else was moving forward while she had somehow gone backwards.
“I felt that because I didn’t have someone to spend a cosy Sunday with, my life had no value,” she admitted.
“Looking back, I’m mad at myself for believing that and letting it affect me and how I date so much.”
Wanting so desperately to get back to the position she had just been in, Jennifer found herself trying to create what she had built in five years with her ex on a first date with someone new — regardless of how suitable they were or whether she felt any chemistry with them.
“It scared a lot of guys off, needless to say,” she laughed. “But the emptiness I felt from not having a partner obliterated any logic from my brain, and I truly believed that if I could just meet or manufacture ‘the one’, everything would be OK and those inner demons would pipe down.”
The interesting part of Jennifer’s story is that so much of her desire for a man wasn’t about the race to start a family, as, for much of this period, she didn’t even want to have kids.
“The ‘biological clock’ wasn’t even part of the issue,” she confesses. “I just genuinely believed that because I was single, I was unworthy, unlovable and that I was somehow ‘less than’ all of the women who were paired up.”
Started from the bottom
The year before she met the man who would become her partner and the father of her child was, in her words, “rock bottom”.
“I was celebrating my 38th birthday in NYC, and I remember very clearly thinking to myself, ‘I just want to find my person, and I do want to be a mum.’”
Sick of dating terrible people and working a job she hated, Jennifer made the decision to move back to Australia at the beginning of the pandemic.
“I was unemployed, single, 38 and living with my mum,” she said. “The world had well and truly humbled me.”
“And then I met Dylan,” she said, smiling. “I am obsessed with my family and our life, and if it all went away tomorrow, I’d be devastated. But I wouldn’t think I have no value.”
“I spent a long time feeling like a failure, but I know now that I have value as my own person,” she said.
And I’ve always said that…
Reflecting on how easy it would have been to just stay in that first relationship, Jennifer urges those having thoughts about leaving to go.
“Spending the rest of your life with someone who makes you feel a little bit less than you are is way scarier than spending some time alone.”
And perhaps that’s the lesson Jennifer wishes she’d learnt much earlier: being alone was never the failure – staying in the wrong relationship because she was terrified of being alone would have been.
Read more columns in the Between Us series, here.
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