Second Chance Series: 7/1

Day 3: Starting Over After Heartache

Welcome to The Second Chances Series, my 23-day writing experiment capturing the joy, mess, beauty, and meaning of my midlife wedding.

I recently got remarried at 57…
…to a widower….
…on a dangerously hot Midwestern summer day…
…surrounded by our seven grown kids and more second-chance energy than I could’ve imagined.

Every day from June 29 to July 21, I’ll post one unfiltered reflection based on moments and photos from our wedding day. I’m doing this to capture all the memories while they’re still fresh in my mind, and to reflect on all that I’m learning about love, grief, joy, and reinvention. And, you’re invited, as always, to share your own reflections on the day’s theme.

This series will also provide a behind-the-scenes look at how I think about and draft material for my upcoming book, co-edited with my husband, Eric, called We Began Again: Collected Essays on Second Chances.

Mockup of our book’s cover

Want to join the project? We’re collecting 750-word essays through 11:59pm Central on 7/21/25. Share your story of starting over—new love, new work, new life, new you. Learn more and submit here.

Some portions of these wedding reflection posts will be free. Most will live behind the paywall to support this work. Thank you for being here.

SCHEDULE OF POSTS

6/29: We’ll Always Have To Start Somewhere

6/30: Beginning Again After Loss

7/1: Starting Over After Heartache

7/2: Fear of Reinjury

7/3: Courage to Start Anew

7/4: When Others’ Renewal Timelines Are Unlike Our Own

7/5: Looking More Forward Than Backward

7/6: The Importance of Acknowledging Loss

7/7: The Surprises of Starting Over

7/8: The Beauty of Beginning Again

7/9: Losing Black & White Thinking While Starting Over

7/10: The Magic of Embracing Stillness When Making a Comeback

7/11: Permission to Be Imperfect When Starting Anew

7/12: How a Community Grows When We Begin Again

7/13: Shock, Surprise, and the Hidden Impact of Starting Over

7/14: Hanging On When All Is Shattered, When All Your Hope Is Gone

7/15: Dealing With Disarray and Disharmony When Starting Over

7/16: Discomfort When Others Aren’t Ready to Begin Again

7/17: Allowing for New Dreams to Come True

7/18: Welcoming Unexpected Joy

7/19: Redefining Success the Second Time Around

7/20: Forgiving Yourself for the First Try

7/21: Final Reflection: Why We Begin Again

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Day 3, July 1
Starting Over After Heartache

Turning around and facing our guests for the first time as married partners (Photo: Chantal Pryor)

Today’s Reflection

Today’s headline is too much like yesterday’s headline, so maybe I’ll just take tonight off and link you to yesterday’s post. No need to reinvent the wheel, amirite? Plus, I’m really freakin’ tired today, so YAY!

I will add, however, one quick thought:

The phrase “starting over after heartache” carries different vibes, depending on how you read it. Emphasize the verb (starting over), and you signal hope, a fresh attitude, strength, and positivity. Emphasize the noun (heartache), and you signal pain, loss, and negativity.

A good reminder, of course, that attitude is everything.

To read the full reflection and support my work, please become a paid subscriber.

Your Turn

Tell us about a time you started over after heartache.

What I Learned About Second Chances:

Looking back at our eight years of dating before marriage, I know that Eric and I both guided our lives toward progress and positivity, rather than dwelling in the sadness of our pasts (Eric’s wife had