I proposed to Anne on a Tuesday. Nothing fancy. No skywriting. No flash mob. Just the two of us and a conversation that had been building for a while. I was 48 years old and more certain about this than I had been about anything in a long time.
TL;DR: I got engaged at 48 after a divorce, a career reset, and years of figuring out who I was without the titles. The timing was not what I planned. It was better. Some things work out specifically because you stopped trying to force them.
The first time around
I got married the first time because it was the next thing on the list. Career, house, marriage, kids. That was the sequence everyone followed and I followed it without questioning whether the timing was right or the match was right. We were good people. We were not good partners. It took us a decade to admit that.
The divorce was hard on everyone, especially the kids. Josie, Kyan, and Sydney had to learn that mom and dad loved them completely and could not live together. Co-parenting Amanda and I figured out over time, not perfectly but honestly. The kids are okay. Better than okay, actually, because they see two parents who chose honesty over performance.
The years in between
After the divorce I did not date for a while. I had work to do on myself and I knew it. The therapist helped. The advocacy work helped. Running a business again helped. Slowly the identity that had been wrapped up in “husband and business owner” got replaced by something more honest: a person who knew what he wanted and was willing to wait for it.
I was not looking for Anne. I was not on dating apps optimizing my profile. She showed up in my life the way the best things do, when I had stopped treating the search like a project with a deadline.
What 48 knows that 28 did not
At 28, I chose a partner based on compatibility on paper. Same neighborhood, same social circle, same timeline goals. At 48, I chose based on how I feel when things go wrong. Anne sees me when I am stressed about work, frustrated with a project, or carrying the weight of a hard week. She does not try to fix it. She sits with me in it. That is worth more than any checklist.
I also know myself better now. I know I need space to think. I know I am a better partner when I am not overworked. I know that I tend to retreat when I am stressed and that I need to communicate that instead of going silent. Twenty years of getting it wrong taught me what getting it right requires.
The wedding
November 21, 2026. The Gage in West Allis. Small. Honest. The people who matter most. I do not need a spectacle. I need a commitment made in front of the people who held us up when things were hard. That is enough. That is more than enough.
About Khary Penebaker
Khary Penebaker is a Regional General Manager at Great Day Improvements, overseeing operations across Chicago, Madison, Milwaukee, and Minneapolis. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership experience in construction, operations, and civic engagement.
Frequently Asked Questions
Is it normal to get married later in life?
The average age of first marriage keeps rising and second marriages happen at every age. There is no timeline for finding the right person. Rushing into it early caused me more problems than waiting.
How do you blend families as a stepparent?
Slowly. Do not try to replace anyone. Build your own relationship with each kid on their terms. It takes time, consistency, and a willingness to be uncomfortable while trust builds.
How does personal happiness affect professional performance?
More than most leaders want to admit. When your personal life is stable, you make better decisions at work. You are less reactive, more patient, and more present. The boundary between work and life is thinner than we pretend.
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Last updated: March 25, 2026