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It was a Monday, and I had taken leave from work to meet a guy I was seeing. But instead of the perfect day I envisaged, he told me that it was over. It shouldn’t be this hard, he told me, let’s try to move on. And then he left me in the middle of Ion Orchard. I didn’t know what to do – I didn’t know who to call or where to go on a Monday afternoon.




I didn’t want to go home and face my mother’s questions, but all my friends were at work. I suddenly remembered one person who had a flexible schedule, so I took out my phone and called my ex-boyfriend, Daniel*. He didn’t answer, so I left him a message asking him to call me back. The distraught exchange was as follows:


If you’re curious, the movie I ended up watching was murder mystery Dark Places. No romance whatsoever.


Turns out, Daniel found a Starbucks and tapped on their WiFi to call me from Korea. It was just a 15-minute phone call, but he was patient and reassuring (especially when I was bawling incoherently, and asking why no one wanted me) and helped me calm down. This isn’t the first time Daniel has been there for me – every time I’m faced with man problems, I always know I can count on him for advice.


Yes, we can all get along

So here’s the truth: I find Daniel’s advice on relationship matters more valuable than that of my closest friends (whether male or female).




The reason is simple. Daniel knows what I’m like in a relationship. We were together for three years and remained friends even after breaking up, for the past seven years. He knows my neuroses; he knows what makes my heart melt and my anger escalate. He knows what matters to me when it comes to dating. And as much as my friends love and care for me, they don’t get the full picture the way he does. So when he dispenses words of wisdom, they hit closer to home.

Daniel isn’t the only one whom I’ve dated and stayed friends with. Craig*, the guy who ended things that Monday afternoon, is another example. For a long time, in my head I thought of him as the one who got away. During our occasional meetings (in groups, as we have mutual friends), I couldn’t look at him without feeling that dull ache in my chest.




My friends thought I was needlessly torturing myself by staying in contact, but I thought back on the good times I had with Craig, even before anything romantic happened. We were pals, and I had faith that we could go back to that again. And to give Craig credit, he never stopped being my friend, though for a period of time he kept a cautious distance. It took time and some torment on my end, but we got to the place I knew we’d end up in – two friends who care for each other.    

And then there was Jasper*, who I went on multiple dates with, and thought was seeing just me, before the penny dropped that I wasn’t the only one enjoying his company. After some tears and reflection, I asked myself if I wanted to stay friends with someone whom I wasn’t sure I could trust. I decided to give it a go, and messaged him saying that I’d like to still hang out, albeit on a platonic terms.




He apologised for being the cause of my tears, and we agreed to restart the friendship, with a promise of honesty on both ends. He’s now become my weekend museum buddy. Some people just make better friends than they do romantic prospects.


You (and him) deserve that second chance

I know my philosophy of staying friends with the people I date is unorthodox. Many people tell me that not being able to make a clean break only complicates matters, and that I won’t be able to fully move on. It’s not untrue – there are occasions where I’ve wondered why I try so hard to resurrect a friendship from a relationship that’s dead on its feet. Even with Daniel, as much as things are cool now, it took a long time for us to get past that awkward post break-up phase.

In the early days, there were moments where I picked fights because I felt he wasn’t considering my feelings enough. In hindsight, I was adjusting from being “girlfriend” to “just friend”, so of course the level of attention would be different. It took at least a year for the discomfort to dissipate.   

There are two reasons why I stick around to try to make these struggling friendships work. The first, admittedly, is shallow – I don’t like the feeling of being forgotten, or relegated to a musty memory. The second reason is that I like to believe that even though two people cannot stay in love, they can still care for each other and want them to be happy. It’s hard work, but then again, all friendships are. These in particular require a lot more work and courage, but the benefits have been invaluable. I’ve found that sometimes, if you give someone a chance, they might surprise you.


Investing in the right people

That being said, there are times when I’ve called it quits. Carving out solid friendships only work if the other party wants the same outcome as you do. That means nobody has a hidden agenda, like hanging around in hopes that you’ll get back together.




My most recent long-term relationship lasted three years, and for a year after we split, I fought really hard to stay friends. Partly because I had remnants of hope that things would work out in the end (a rookie mistake), and partly also because Daniel was such a success story that I wanted Alex* to be the same. But while I believe that Alex was willing, his next girlfriend wasn’t keen on us staying in contact. It reached the point where he had to speak to me behind her back, and after a year of this, I finally cut off communication.

It also goes without saying that if the relationship was toxic, then there’s little point in trying to salvage it. There have been men I’ve dated whom I’ve kicked to the curb (there was one who hid the fact that he actually had a girlfriend) – just because any kind of subsequent friendship would have been damaging to me. As we get older, we’re more selective about the friendships we invest in, so if you think an ex is more trouble than he’s worth, I say shut that door, lock it, and toss the key into the fiery pits of Mount Doom.




*Names have been changed.