The Secret to Rekindling Relationships with People from Your Past — Without Being Awkward

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Sharon M. Cirillo34
Content Creator and Ghost Writer
April 13, 2024 at 8:20PM UTC

At some point during life on this planet, most of us will engage in the uncomfortable experience of wanting to, or needing to, rekindle a relationship from the past. It could be an old friend who comes back into your life or an old boss who's hiring for your dream job or a firm you wish to re-join. In some cases, you may not have left off on the best terms. You might have previous hurts or disagreements that loom in the backdrop and color the way you show up.

So, what is the best way to handle these awkward situations when they arise? Authenticity. 

Amid all the tips, tricks and strategies offered around cultivating conversational expertise, I invite you to make things way less complicated by showing up sincerely and authentically. Authenticity is like a muscle that grows stronger the more we use it.

Rather than tripping over repeated apologies, making excuses for hurt feelings or previous experiences, consider staying in the present and addressing any possible issues right on the spot. Here's how to communicate authentically in multiple scenarios. 

For scenario one, let's take a prior boss, for instance. 

You quit, and although you didn't burn bridges, the reality is you decided they were not the company for you anymore. Now, a few years later, you see a new position that you want to apply for and the gnawing feeling in your tummy precludes you from making the call. What will you say? What did people discuss after you left the firm? Awkward!

Suggestion? Say something like this: "Hi, Paul, this is Maggie. Thanks so much for taking my call today. I hope all is well with you. I'm excited to see the position for Senior Account Manager is available in the ABC Company's New York office. That was a role I always aspired to, and during the last few years at XYZ Corp., I've gained valuable experience which I believe makes me a great candidate. I always loved working at ABC and appreciated the way you understood when I needed to expand into a different role. I would love the opportunity to interview again. Would you be open to discussing this with me?" 

Takeaway? When you chose to go, you were evolving in your career, as people do. It's not personal; it's business. Stay in that mindset. 

In scenario two, you run into an old friend at your college reunion. 

The friendship came to a screeching halt, when several months after she dated a man, he had an interest in getting to know you. Now here you are, face-to-face, realizing that you are both happily married, have kids around the same age and you have a strong desire to pick up your friendship again. Awkward!

Suggestion? Say something like this: "I am so happy we ran into each other, Susan, it's great to see you! It seems we have so much in common again, and I am sorry that we let Rick come between us. To think that we allowed an ex-boyfriend that neither of us even married hurt our friendship. I hope we can start over again because you mean so much to me. Let's promise each other to talk things out if anything should ever come up for us again." 

Takeaway? Being vulnerable, stating your apology and letting her know what the friendship means to you even in the face of rejection is what matters regardless of the outcome. 

Authenticity is the great equalizer. 

It's not always the easy thing, but it's the best approach. There is no need to qualify the past or try to pretend that possible wounds or awkwardness aren't there. When we keep it real, people see the effort we are making and appreciate having the opportunity to clear the air. If you are feeling awkward, they likely are, too. 

To have the best impact, you should be equal parts sincere and vulnerable, with a splash of lightheartedness, knowing the discussion might encounter some resistance. If it does, you should keep responding in an authentic, compassionate way. It may not always work out the way you envision, but knowing you tried to make things comfortable keeps you on the high road. 

Speaking our truths, from the heart, has a way of diffusing even the most uncomfortable of situations. Stick to the facts and take emotions out of the responses and you can make the best of tricky situations from the past. If an apology is needed, make it sincere and up front. 

People from our past are not always meant to remain there. Sometimes a relationship will come full-circle again as part of our life plan. If it feels awkward at first, know that you have the power to shift and re-frame the interaction by choosing your approach and words wisely.

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