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Decoding the “right person, wrong time” dilemma: Is it ever worth reconnecting?

We delve into the pros and cons.

Feb 28, 2025
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Timing is everything in life, especially when it comes to meeting the right person. Few things are more painful than meeting the right person at the wrong time. Two people might share great chemistry and a deep connection, but unforeseen circumstances—such as a career change, moving away, or unresolved past issues—can get in the way. This can leave both individuals stuck in a cycle of ‘what ifs,’ grappling with regret and sadness over what could have been.

That said, it’s never too late to start fresh and revisit a relationship that didn’t work out the first time. But is it the right thing to do? Let’s explore the pros and cons.


Here are some reasons why it may be a good idea to reconnect.

Change has taken place for the better

If both individuals have grown personally since they last met, it could set the stage for a healthier, more fulfilling relationship. With greater maturity and self-awareness, rekindling an old connection might just feel right.

The need to attain closure

Unfinished business can linger long after two people part ways. Reconnecting to address unresolved issues can help clear the air, offering both parties the clarity they need to move forward.

The timing may finally be right

Life circumstances constantly change. What was once an obstacle may no longer be a barrier—career goals may have been achieved, or distance may no longer be an issue—allowing the relationship to flourish.

What’s meant to be, will be

True connections are rare. If the bond was genuine and meaningful before, revisiting the relationship might be worthwhile. People change, circumstances shift, and what once was could evolve into something deeper. If the connection is strong enough, it might take on a new form, even if it’s different from what you once imagined.

 

And, of course, sometimes, reconnecting can be a bad idea. Here's why. 

People just don’t change

While personal growth is possible, certain habits and tendencies remain deeply ingrained. Someone who struggled with commitment, communication, or emotional availability in the past may not have changed just because time has passed. Reconnecting can bring back old wounds, leading to the same unresolved issues resurfacing and causing more emotional distress.

Romanticising the past

With time, memories can become selective, causing people to remember only the good moments while minimising past conflicts. This nostalgia can create an illusion that things were better than they actually were, making it easy to overlook the reasons the relationship ended in the first place. When emotions cloud judgment, it becomes difficult to objectively assess whether the relationship is truly right for the present.

The risk of getting hurt again

Revisiting an old relationship often comes with expectations, but if things don’t unfold as hoped, the emotional toll can be even greater. The pain of reliving familiar disappointments or realising that nothing has changed can make it harder to heal. A fresh heartbreak, especially one that repeats past patterns, can deepen feelings of regret and make moving forward even more difficult.

Prevents new opportunities

Dwelling on the past can prevent one from embracing new relationships and experiences that better align with the present. Holding on too tightly makes it difficult to fully engage with the potential of the future. Growth comes from accepting change and staying open to fresh perspectives.

Deciding whether to reconnect with someone from the past is a deeply personal choice that requires careful self-reflection. Sometimes, the right person at the wrong time can become the right person at the right time—if both individuals have truly evolved and are willing to start anew. Whether it leads to rekindled love or much-needed closure, reconnecting can be a meaningful step in one’s emotional journey.

Lead image: Netflix

Also read: How my breakup gave me a sense of clarity

Also read: Is taking a break from your relationship healthy?

Also read: How to get over a break-up in 21 days

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