Episode 25 - Dating a Best Friend's Ex Revisited

Updated: Nov 12, 2020

Best Friend's Ex (The Sequel)


In this week’s episode, we revisited the topic of “Would you date your best friend’s ex?”. If you remember in that episode; Rumbi talked about how her best friend, Michelle, was deeply reluctant to date someone Rumbi had briefly known a few years prior. We were curious about why this was such an issue for her, so we brought her on to expand on her side of things!


To listen to this episode, click here!


Given that Rumbi’s connection to this guy in question was minimal at best, Michelle confesses that all those years ago, her main problem was a touch of insecurity. Which is completely understandable; picture this – you’re interested in someone who’s already been intimate with a friend of yours (many years ago), the natural thought would be “how do I compare?”. It’s much easier to deal with a guy’s ex when she’s outside of your circle, you can think about her if you want or you can completely erase her and it won’t make a difference – ideally, their history will have minimal impact on you. However, when your feelings are involved and you know that there was a hint of a spark between your love interest and best friend, you’d probably take into account the possibility of that spark re-igniting and growing into a fully fledged Guy Fawkes bonfire. This can feel like an even bigger issue when your friend and partner genuinely get along like a house on fire.


To flip this scenario on it’s head, how does this work from a man’s point of view? Is it really harder for men to ‘go there’ with you emotionally when their friend has already been intimate with you, regardless of how meaningless it may have been? Yet they typically don’t mind pursuing a simple sexual relationship that’s already been explored (wink wink) by their friend? We’d be really interested in knowing how men navigate this when there are emotions, pride, ego and loyalties all at stake.


We go even deeper into the relationship talks and discuss the lessons Rumbi (being the only Mrs in the group) has learned in marriage. Having been advised to ‘strike while the iron is hot before you start seeing those cracks’, in other words – get married during the Honeymoon Phase before things get real. This really begs the question “how long should you spend getting to know someone before you know if you can spend your life with them?”. We have the general consensus that it’s really not that long. Provided your partner isn’t hiding a huge secret eg. serial killer dungeon in the basement, then you’ll have picked up on all their positive and negative qualities (on some level) within the first year of your relationship. A lot of people think that you’ll only experience those same things at varying intensities when you live with them. Basically, people are unlikely to surprise you with brand new parts of their personalities, because whether you like it or not… your conscious or subconscious mind picked up on it during year one.



That being said, you may be surprised at how much you’ll dislike some of these pet peeves when you live together. Imagine almost breaking off an engagement because he ordered the wrong pizza topping for you. Or ending a relationship because he used a butter knife instead of a steak knife. Yep, all real-life examples. These all sound ridiculous but that’s exactly what it looks like when that final straw breaks the camel’s back! Michelle offers some insightful advice in saying that the best way to know if you can cope with your partner for life is to complete a project with them, it can be anything from redoing the garden to a house renovation. This is when you can observe your innate expectations of one another and your potential approach to the lifelong project that is marriage.


Let us know what you think of this episode, what kinds of blockers have stopped you from getting to know someone that you now look back and think “I should have pursued that”? Even if it had worked out, how long do you think is necessary for marriage minded individuals to get to know each other? Let us know how long you dated your now spouses and whether you think you could have married them earlier or later.

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