Should I Date My Friend’s Ex?

Written by O. Hadgie, who believes that a bad experience eventually becomes a good story and that everything is a chance to learn and grow.

4 min read

The age-old question. In the ancient texts, when the laws of friendship were written, one testament was written above all else. In bold. Underlined. Twice. Never Date Your Friend’s Ex. It’s something most people wouldn’t hesitate to deny. But life is rarely that simple is it? 

We all know the scenario (and if you don’t I severely envy your friend group):

• You meet someone. 
• Despite all the odds, you start talking and really click with them. 
• They get your humour, you feel good around them, and bonus points: , they’re hot as hell. 

If Cupid had pulled his arrow at this exact moment, there’s nothing he’d change. It’s all going perfect!! 

Except… they previously dated your friend. 

Dating your friend’s ex is awkward, right?

On a scale of saying goodbye to someone then walking the same way, to calling your teacher “mum”, dating your friend’s ex is definitely awkward. You don’t want to mess up the relationship with your friend but you also don’t want to say goodbye to the meaningful relationship blossoming before you;. 

You have no clue how your friend will react let alone all your mutual friends who are along for the ride.

It’s certainly a tough one and I can’t say whether I can honestly solve this one. However, I can give you some tips that may or may not come from some messy personal experience:

THINK THINK THINK ABOUT IT

The thing about relationships is that it’s easy to get caught up in things. You like them, they like you, why should it be more difficult than that? Your friend cares about you so shouldn’t they want you to be happy?
 

To that, I say this: slow your horses cowboy. 

First things first: when making any sort of decision, you need to examine the facts. Feel free to pull up a pros and cons chart, Devi Vishwakumar-style, if you must.

ASK YOURSELF, IS YOUR FRIEND OVER IT?

This one gets written in big red letters.

Relationships and, by extension, breakups can be incredibly complicated, creating problems that fester for months or even years. Often the tip of the iceberg doesn’t cover half of what has occurred. Just because your friend might be pretending that everything is okay doesn’t mean they’ve actually processed and moved on from whatever led to them and the ex splitting. 

Whether for personal pride or trying to save face, they might just be pretending to be okay with it. Your sudden relationship with their ex might be the straw that breaks the emotionally volatile camel’s back.
 

Was it a month-long fling or had they been going steady for years? These factors can severely impact the sort of reaction you’re going to get when you finally break your news to your friend.

HOW DID THEIR RELATIONSHIP END?

Break-ups can bring out the worst sides of people as emotions run high, hot and heavy. This is a big thing to consider when thinking of dating a friend’s ex. 

Maybe the relationship ended quite amicably:. Both parties realised that they were better off friends and so friends they are. The break-up happened months ago and everybody is happy. Your friend clearly separated from their ex without too much flint and fuss. Doesn’t seem too bad.

But what if the break-up was a bit more explosive? Did their ex initiate it? Was there some betrayal of trust present in this parting of ways? If so, you might want to take a moment to consider what you’re doing. If they broke up on bad terms, your friend might think that their ex is only dating you to get back at them. And they might be right. 

When people are hurting emotionally, decision-making is at its least rational. Do you really want to be caught in the cross-fires of a potential cold war between your friend and newly-found flame?

IS DATING YOUR FRIEND’S EX WORTH IT?

Love is stronger than a lot of things. We have about 4000 years of literature to prove it. It’s broken through borders, conflicts and expectations. It is the source of the greatest pleasure and even worse heartbreak. 

If you think you’ve found love with your friend’s ex, then I understand your haste to begin your thrilling love story. But life isn’t like the movies. Emotions aren’t just ways to advance a plot. Instead, they can have genuine, painful consequences. You have to come to terms with the fact that by going after this person, you might lose a friend. 
 

The best case scenario is obviously that your friend is incredibly happy for you both and they end up being enthusiastically part of the wedding party. However, you have to recognise that they also might never be okay with you dating their ex — they, might even see it as the ultimate act of betrayal.

If they’re only an acquaintance, then maybe you’ll be able to stomach this loss. However, if your friend means a lot to you, then you might be finding yourself at a cross-roads of sorts.

There are plenty of fish in the sea but finding a good friend can be like picking a needle out of a haystack. 

Love conquers all but trust is what keeps it together. Some bonds are broken in favour of building stronger ones. Others just lead to heartbreak all round. 

Deciding whether to date your friend’s ex

At the end of the day, this decision comes down to you and your unique situation. It’s a choice that needs careful consideration of every person involved and all the consequences that could occur. It’s not like the romcoms where one heartfelt speech leads to hugs and kisses and hot new partners for everyone. 

But who knows? Life works out in funny ways and maybe this time, it’ll work out for you.

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