A Question Of Exes: Is It Wise To Re-Date?


Michael Stagliano & Holly Durst broke up and then dated again before filming "The Bachelor Pad 2"

I have a CM friend that sums up re-igniting relationships this way: “Only dogs go back to their own vomit.”

Another friend likens it to watching re-runs: “Even if it’s your favorite program, you know exactly what’s going to happen – including how it’s going to end. Why bother?”

So I was reluctant to tell either one of them that I started seeing someone that I dated three years ago, especially because I thought I’d never go out with him again.

But interestingly enough, I had an image from a television program my sisters often re-watched. In it, the heroine declares to her parents that she wouldn’t go out with a certain young boy “even if he was the last fool on earth.”

The next scene is her wedding. To the young man she swore off. Aren’t women known for changing their minds?

This relationship was different. Although it ended with me in the midst of depression, he, in a relapse – it didn’t end entirely.

Six months after we’d broken up,  I got a text from him asking about the roses he gave me. I quickly found out he’d hand-delivered nine white roses to the front desk of my building; not forgetting that he never knew how to get to my neighborhood, much less my home. I then found out my mother had finished a novena to St. Therese of Lisieux the same day he delivered the roses. He was unaware of what my mother had done.

One would think this would soften even the hardest of hearts.

But I wasn’t ready. I’d still been running my fingers over the scars from dating him. I couldn’t give him my heart again, not yet.


A softened heart

A few months ago, however, I was asked to write an article about the intercession of a saint. The roses was the best story I had, so I re-lived it in writing about it.

The scars were completely faded. I softened. I emailed him and thanked him once again. His only response was to send a link to an exhibition at the Metropolitan Museum, where I’d been working when we dated. We never missed an exhibition during that time.

It seemed as if we picked up where we left off, minus the issues: the angst, the depression, the fear, the anxiety and the unrest.

It just felt right – calm and positive. We both looked at each other and thought, “Why not? What is there to lose? If worse comes to worse, we walk away.”

The next morning, however, we each emailed that maybe it wasn’t a great idea. He said, “It is a brave experiment,” fully acknowledging the need for hesitation. We took a few days to pray about it.

In addition to asking for divine guidance, I thought of my standard go-to exercise, the pro/con list. It is an exercise taught to me by my sister, who is an endless source of good advice and level-headed thinking.

We both told ourselves that because we’d already gotten to know each other, there would be no surprises; particularly because each of us saw the other in their darkest moments. This was a good thing, something to add to the “pro” column.

But we were both concerned about settling into old patterns again – reacting to things the way we used to, starting up the same old arguments, re-living some of the old issues. This was most definitely a “con.”

There were a few other items on the “con” list; namely, that if it was going to work, we might resent the time we’d spent apart. But if life had taught me anything, it was not to regret the time that was lost. Chalk it up to preparation time.

Then something occurred to me: We had a most extraordinary gift in this experience, the opportunity to forgive.

I was reminded of my mother’s words to me once: “All love leads to the Cross.”

Was this opportunity not the best example of living the love of Christ? In forgiving our past wrongs and accepting each other, weren’t we  acting on the words of Jesus? Here was a chance for a wonderful moment to live out His Word.

This was the  biggest “pro” and was what sent me back to the computer to answer an email to him: Well, really, why not? It truly is a brave experiment. And it’s a chance to live out His word.

Isn’t that worth a try?




Further reading

Our Jessica Zimanske breaks down a Psychology Today article on dating an ex. Read it here.



  1. Robert-435781 September 14, 2011 Reply

    Once they leave; they leave. No do overs!!!1

  2. Daniella-762796 September 14, 2011 Reply

    I deff agree with forgive and forget. It’s part of our Catholic faith! “If you love somebody, let them go. If they return, they were always yours”…. you both were obviously meant to be 🙂

  3. Brian-465776 September 13, 2011 Reply

    Nice story. But, one can see that the “door was not closed”. This was just a romantic break-up, not a divorce. And, I am sure there were good times remembered. Because of these, there was still a chance of re-igniting the romantic spirit. Hopefully in a “more mature” manner. Now these two can continue this relationship as lovers and as friends. That is the best way to go.

  4. Careese-449851 September 11, 2011 Reply

    I love this on many levels.

  5. Sherrill-anne-13557 September 11, 2011 Reply

    Many do settle their differences and get married.It takes a conscious effort on each person as well as positive communication.
    Your mother is wise indeed all love does lead to the Cross.Read something similar in the book Marriage :Path to Sanctity
    Thanks for sharing

  6. Jim-397948 September 11, 2011 Reply

    I would love to date an ex…Only if it makes her happy….but I would not stand in her way to find someone better than me.

  7. Tammy-492301 September 9, 2011 Reply

    (: Loves me this! <3

  8. Yiqin C. September 9, 2011 Reply

    faith,hope,love .sounds good,nice!thank you for sharing it..dunk sb

  9. Yiqin C. September 9, 2011 Reply

    faith,hope ,love.good ,nice!thank you for sharing..dunk sb

  10. Anna-731422 September 9, 2011 Reply

    In the past, I’ve always lived by a firm rule of mine to never date an ex again. The way I look at it, if it didn’t work the first time, it probably won’t work the next. However, I admire the people who can look past the mistakes and heartaches that were present during their relationship the first time around and make a go of it again. Thanks for the article, Catherine.

  11. Tina-645657 September 6, 2011 Reply

    The opportunity to forgive is a brave behavior and a kind gesture and should be left at that, however to re-date an ex is never a good idea. Past experiences always dictates future experiences. For whatever reason it didn’t work out the first time around, chances are it will repeat itself. Move forward and never look back.

  12. Michael-422117 September 6, 2011 Reply

    Thank you for writing this piece, Catherine. It’s comforting to know that sometimes it IS possible for two people to find their way back to each other.

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