How We Dealt With Heartbreak

Two women, two very different reactions to a break-up. Clara How swore off men for six months, while a woman Hoe I Yune spoke to went on a dating spree to get over her ex. Extreme choices, no doubt, but both women took away lessons in love.

Portrait of Tammy Strobel
Two women, two very different reactions to a break-up. Clara How swore off men for six months, while a woman Hoe I Yune spoke to went on a dating spree to get over her ex. Extreme choices, no doubt, but both women took away lessons in love.
My Reading Room

In early 2015, I found myself at my lowest, crying under my desk at work. I had been typing on my keyboard, tears running down my cheeks, when I glimpsed my boss heading my way. Ninja-like, I ducked under my table until the coast was clear.

The cause of my distress was realising that my ex-boyfriend had a new girlfriend, just weeks after we’d split up. We had been together almost three years, and I was adjusting to my new normal, which meant we were still texting and exchanging e-mails. But that day, I received a two-line e-mail telling me that all contact between us would have to stop. It was my first real heartbreak, and I completely fell apart. I wallowed in selfpity for months, but at some point, decided I had to meet a new man, someone who would blow my ex out of the water.

That didn’t happen. I fell into a dark hole of dating men who enjoyed my company, but didn’t want to commit. One guy ghosted. Another said we didn’t have a connection. A third told me he wasn’t looking for anything serious. My self-esteem took a beating. “What’s wrong with me?”, I wailed to a close friend. The last straw was Zach*. We met on a dating app and hit it off. After two months of frequent texting, we went for a movie, and drinks after. Things looked promising. But on our second date, he dropped a bomb – he wasn’t looking for a relationship. It was one more rejection I just couldn’t handle.

That was Nov 19, 2016, and I decided I would swear off men for a year. That meant no swiping on apps, no meeting new men, and even if I was asked on a date, I would keep him strictly in the friend zone. I saw it as my Eat, Pray, Love dating sabbatical, minus the exotic destinations. For the first time, I would be consciously single. Previously, I’d had periods of not seeing anyone, but that was a reluctant single hood. The aim of this year-long man drought? To understand myself better and the type of man I wanted to date, figure out what was really important to me, and stop fretting about when the one was going to show up.

So I went forth, bright-eyed and bushy-tailed, into my year. Starting a new job helped. I was also determined to make the most of all the extra me time, so I signed up for barre and aerial fitness classes, and even a burlesque workshop – anything to push me out of my comfort zone. For once, I was doing things just for me. Burlesque, for example, was a way to get comfortable in my own skin rather than please a man. Solo trips to the cinema or exhibitions, and reconnecting with old friends, became a new normal. I started cooking again, and rediscovered the restorative effects it had on me.

Three months in, I had a breakthrough. One Saturday, I had the afternoon to myself and chose to chill at a quaint cafe. Sitting in a sunlit room, eating mushroom pasta and sketching birthday cards for friends, I felt an unfamiliar sense of contentment. It dawned on me that this time was my own, and I was free to do whatever I wanted with it. It was so different from before, when I would feel resentful about being alone. That day, I began to appreciate the fact that by fixating on what I didn’t have, I was missing out on what I did have – a job that gave me a great deal of personal satisfaction, and a healthy and active social network, even without a plus-one.

I was happy with the changes I saw in myself, and curious about whether my new-found perspective would truly have an impact on the way I dated. So on May 13, 2017, I decided to dive back into dating.

My first big test came pretty quickly. I reconnected with Zach, and everything was as good as I remembered. He texted every day, we met up regularly on weekends, and we were obviously attracted to each other. I didn’t rush into anything. What stood out this time around was how comfortable I felt with being alone, even though I was dating again.

On one date at a museum, Zach left early for dinner with friends. Before this, I would have been crushed that he was taking off to spend time with others. Now, instead of moping, I treated myself to squid ink risotto at Symmetry and after that, saw a performance of Tango at the Drama Centre. Did I miss him? No.

After five consecutive weekends of dates, I asked Zach if he’d like to make things exclusive, since he didn’t appear to be seeing anyone else. Turns out, he was. I was crushed.

I woke up the next morning with a clearer head. I recalled the episode of crying under my desk a year before, then thought about the night I had gone to the play on my own and enjoyed myself. I had worked so hard to get to a place where I could be happy and contented; I wasn’t going to let this guy derail me so easily.

Once it became clear that Zach wasn’t worth it, my sadness abated. I’m sure he won’t be the last example of things not working out on the romantic front. But while I can’t control encountering men who don’t want the same things I do, I can control the way I react, and do things on my own terms.

Months after the experiment, I’m still single, and meeting new people. But I also take myself out on solo dates to new cafes or haunts that I want to check out. I buy myself flowers, and I pick up new hobbies. I’ve learnt that the person who can ultimately make you happiest is yourself.

I quit men for six months
My Reading Room
My Reading Room

I dated seven guys in seven days to get over my ex

When my boyfriend of two years, Ben*, was away, I swung by his flat to help tidy up since he lived alone and had been gone for a while. In his study, I chanced upon a crumpled piece of paper with a phone number and an e-mail address on it. There was no name, but the handwriting was feminine, and my intuition told me something was up.

So I looked up the details on Facebook. A woman in her 20s stared back at me, unabashedly flaunting her doubleDs in a low-cut tank top. I told myself to get a grip. Ben and I were happy together. Or so I thought.

A few months later, Ben broke up with me. He didn’t explain, but deep down, I knew. Not long after, pictures of him and that same woman began surfacing on Facebook. In fact, it was so soon after the break-up, I was sure I dated seven guys in seven days to get over my ex he must have been seeing her behind my back. It stung, especially since Ben was the first guy I had really fallen for.

I decided that the only way to get over this was to fill the gap Ben had left as quickly as possible. Before the break-up, my life had revolved around him. Now, the chance to date other men might just be the boost my shattered confidence needed.

I decided on a dating frenzy, meeting men through mutual friends and dating apps. At the height of it, I was dating nine guys at the same time. I know it sounds exciting, but in all honesty, it was completely exhausting. At one point, I even went on dates with seven different guys over seven consecutive days. Juggling so many men at one time was tough. Texting them also became a complete drag. Evenings were the worst, when many of them would spam me with texts post-work. Replying to all of them became impossible, because I’d be doing nothing else for the night.

I would buy myself time by not replying until the next day, or even a few days later, so they wouldn’t think I was a speedy texter. Excuses like being super busy at work, or needing an early night, soon rolled off my tongue easily. But there would still be slip-ups because it was so hard to keep track of all of them, especially in real life. Without a chat history to refer to, I would often forget who said what. Once, when I was out with one guy, I made a reference to a conversation I’d had with another, only to be met with a confused look. There were also times when one of the guys would call while I was on a date with someone else. I have to say that dating so many men at the same time is truly an art – one for which I had absolutely no aptitude.

These men were a mixed bag. Eric* was three years younger and deeply insecure – always wanting to know where I was and who I was with. Then there was Alex*, whom I met at the gym and later told me he was into both men and women. After Alex came Kendrick*, who expected us to split the bill on every date. Once, at the movies, he told me I’d have to get my own tub of popcorn, because he didn’t plan on sharing. Even worse was Aaron*, who would always order more food than he had cash for, which meant I’d wind up handing my card over while he reassured me he’d pay me back (he never did). And Jason*, whom I met at a bar, was only interested in taking things to second base and beyond.

My dating bender came to a head when I started seeing Greg*, who was in my yoga class. He turned out to be good friends with yet another guy I was seeing, Ian*. And they both knew about each other. Greg was upset, but seemed to use this as motivation to keep asking me out. Of all the men I was dating at the time, I enjoyed Greg’s company the most. He was goodlooking, engaging, and had a great sense of humour. We eventually ended up dating exclusively for four months.

After we split up, it dawned on me that although I enjoyed the attention these men had given me, it didn’t feel fulfilling. Maybe serial dating just wasn’t my style.

I decided to give the dating spree a break. During this time, Ben came back into my life. When I found out he was no longer with that other woman, we started spending time together – first as friends for a year, before we made the call to give things another go.

Ben’s a lot more thoughtful and caring now. I’m glad we decided to try again, because finding someone you connect with, and who has similar values and interests, isn’t easy. Looking back, it’s funny that I had to date so many men before realising this.

*Names have been changed.