Writers' Haven by Christine Wolf

Writers' Haven by Christine Wolf

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Writers' Haven by Christine Wolf
Writers' Haven by Christine Wolf
Second Chance Series: 6/30
Second Chance Series

Second Chance Series: 6/30

Day 2: Beginning Again After Loss

Jul 01, 2025
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Writers' Haven by Christine Wolf
Writers' Haven by Christine Wolf
Second Chance Series: 6/30
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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.

Cover image of the book WE BEGAN AGAIN: Collected Essays on Second Chances, edited by memoir coach Christine Wolf and her husband, Eric Ronne
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.

Submit Your Second Chance Essay by 7/21

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


Day 2, June 30
Beginning Again After Loss

Blonde woman in ponytail and glasses on a FaceTime call with a man playing guitar)
An early FaceTime date (Screenshot: Christine Wolf)

Today’s Reflection

Whenever I consider the date that Eric and I first “began” as a couple, things feel a little murky…at least in my overthinking mind.

Is it the first time he reached out to me on OKCupid and commented on my profile?

Is it the first time we met in person (two days later) for a proper date?

For the past 8 years, I’ve honored both dates equally as the “start” of our relationship, but the more I think about it, the more I realize that we began as a couple much earlier than that. We began as a couple when we individually decided to begin again after loss.

Eric’s wife, Amy, passed away after a battle with cancer in 2012.
My marriage ended in divorce.

We’d each been married 26 years.

By the time I met Eric in 2017, he’d been a widower for almost 5 years.
Though I’d been separated for more than a year…I was less than 6 months into my dating journey and already determined to call it quits. The emotional rollercoaster of dating life was NOT for me, so I was already shutting down my dating apps and envisioning single life forever. That first meeting with Eric changed all that.

Eric felt like family from the moment he walked into the restaurant: kind, bashful, friendly, warm, and genuine. I felt immediately comfortable and at ease in his presence. He was handsome and charming yet clearly unaware that this was so. He wasn’t trying to impress me: he was interested in getting to know me. And, despite my asking a gazillion questions (that’s me!), he never flinched. Not once. By the end of dinner, I was smitten, and our first snowy kiss — under a streetlamp — felt like living in a movie.

I saw Eric again a couple of days later, and by the end of that date, we’d decided to try being a couple.

There was never a game of “chase.” I never wondered about how he felt. Together, we took the leap, and that was that. Awash in love anew, we were filled with happiness and hope about all the joyous moments yet to come.

Almost immediately, I began researching the topic of dating a widower, and I joined an online support group for women who were dating widowers. I had so many questions, and figured I’d get some answers by learning from “experts” and from women familiar with this dynamic.

Eric and I lived an hour apart, so we often FaceTimed before we went to sleep. We’d talk about our days, our kids, our work, and our pasts. Oftentimes, we’d solve the New York Times crossword together (he was so much better at it than me, which was a total turn on, lol). Sometimes, as I brushed my teeth, Eric strummed on his guitar. I don’t play any instruments and I can’t carry a tune, so I was mesmerized watching him play by ear. In these tender, early days, we couldn’t have imagined all the unforeseen landmines we’d eventually have to navigate. For now, as we eased into a gentle partnership, I found myself falling slowly and deeply in love.

To be sure, I was terrified that I’d get hurt again. Terrified I’d “miss” something. Could I trust this man? Was he actually this kind…this calm…this thoughtful? Or was it all an act? Would I someday discover he was someone else? I was still healing from relationship devastation. Was I ready for something serious? Was he? How do people do this? How does anyone know how to proceed?

I can only imagine the questions Eric had about me. Why did her divorce of 26 years end? What role did she play in the breakup? Is this a rebound relationship?

[I should write a separate post about all my dating blunders. There were some incredible stories — like, some Moth GrandSLAM-worthy stories. Thankfully, I’d dated enough duds before meeting Eric to know exactly what I didn’t want.]

What I wanted was someone who, like me, loved their kids… and who was eager for a true partnership… someone who could communicate their feelings… and who accepted me as I was…

The longer we dated, the more evidence Eric gave me that he was all these things, and more.

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

Your Turn

Consider a time that you began again after loss. What was the process like for you? Did you agonize, or debate yourself internally, over anything? Did the “you” before your loss try to warn the “new you” about anything? Was your attitude more tentative or badass as you stepped into your new chapter?

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What I Learned About Second Chances:

When I first stepped into the midlife dating world, the “ick” factor was through the ROOF. Dating was hard enough as a teen and young adult, and I hadn’t been in that world for close to three decades. But there were two people — two men, actually — who gave me the absolute best dating advice…

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