Dating horror stories: Dating as a Baby Boomer was the worst - Los Angeles Times
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L.A. Affairs: I was a divorced dad with an empty nest. Was I doomed to be single?

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I’d come home from another good day at my middle school teaching job, but my spirits sank as I opened the front door to that hollow feeling of an empty house. As I checked the mail, I found a large envelope addressed to me by hand. Hmmm. Never got many of those. It was from Jere Johnson, a name I didn’t recognize.

I opened it to find several impressive editions of a middle school newspaper -- the Bonita Vista Scroll -- with a note attached from Jere. She introduced herself and said we had many mutual friends and that she had been given my mailing address by a fellow teacher named Phyllis. “I thought it might be fun to share publications,” she wrote. I too was a newspaper advisor, and as I glanced through the school’s newspaper, I found Jere in a photo. “Wow!” I thought.

The next day at school I tracked down Phyllis: “So, who is Jere Johnson?”

“Jere!” she said gleefully. “She would be perfect for you!”

Like all my pals, Phyllis was all too aware that I had been alone for many years after my divorce. It wasn’t that bad when my daughter was living at home, but at the time she was in college back East. Phyllis told me a bit about Jere. As it turned out, Jere and I had much in common. Both her daughters had graduated from college and she too was looking to start a new chapter in her life.

I had spent time on Match.com trying to find romance with someone my age, but after countless first dates and few second dates, I decided to give it a rest. I had been alone for 15 years and sometimes wondered if I was ever going to meet that someone special.

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I called Jere that night to thank her for the newspapers. I shared my enthusiasm for her publication and we connected right away, as teachers do. (We also commiserated about the trials of middle school teaching.)

Although I generally thought it best to spend time getting to know someone before risking rejection, in this case I decided to give it a shot. “I know this is short notice, but if you happen to be free on Saturday night, I’d like to take you out to dinner,” I said, and suggested finding a place in her neighborhood in San Diego.

“I know just the spot,” she said, and my evening brightened considerably. Funny how everything takes on a glow when you have a date for the weekend.

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Saturday night found me knocking once again on a first-date door. Nervous but not a wreck. If it didn’t go well, life would go on. I knew enough not to be taken in by first impressions, but when the door opened, I couldn’t help myself. Prettier than her picture with a warm, welcoming smile. So far, so great.

We ended up tucked in at the corner table at Volare in Point Loma, and we spent the evening getting to know each other. As baby boomers, we had an instant connection: We laughed about watching old western TV shows like “Rawhide,” “Bonanza” and “Wagon Train” and that we could still sing their theme songs. As for popular music, we grew up on Elvis and matured with the Beatles.

Heck, our moms even cooked the same dinners: meatloaf, spaghetti, fish sticks, chicken pot pie and roast beef on Sundays. We discovered not only a shared past but found out we liked the same things: books, movies, plays, board games, sports, travel and crossword puzzles.

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Digging deeper, we realized that we both knew the pain of divorce, the challenges of single parenting and the sadness of lonely nights.

After our meal, I asked Jere, “Do you like ice cream?”

The smile that was winning my heart said it all. After two scoops and even more intimate conversation at Baskin-Robbins, neither of us wanted the evening to end. We went back to her place to play cribbage.

When it was finally time for me to make the drive home, Jere mentioned she had tickets to a play at the Old Globe theater in about a month. Would I like to join her?

“Great! Just so you don’t make me wait that long to see you again.”

Her drop-dead gorgeous smile told me all I wanted to hear. A goodnight kiss sent me home dreaming that this might really work.

The next few dates involved a walk on the bluff at Torrey Pines beach and a visit to the Getty Museum. The play turned out to be a dud, but the date itself was good.

It didn’t take me long to know that Jere was Mrs. Right. And she seemed taken with me. The next hurdle was the daughters. (Although they were all out of the house, they were very much in our lives.)

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Fortunately, everyone hit it off.

Deep down, I think, they were relieved we each had finally found someone.

The last 20 years have been bountiful. Jere and I led student tours to Australia, Europe and Central America and then sold our condos to buy our dream house in Point Loma before retiring.

We were blessed by each daughter’s marriage and now spend weekdays helping our six grandchildren with school work and weekends at their sports games.

Every anniversary we marvel at our good fortune by reenacting our first date. We dine at Volare and toast our good friend Phyllis for bringing us together.

The author is a retired middle school teacher in San Diego.

Straight, gay, bisexual, transgender or nonbinary: L.A. Affairs chronicles the search for love in and around Los Angeles — and we want to hear your story. You must allow your name to be published, and the story you tell has to be true. We pay $300 for each essay we publish. Email us at [email protected]. You can find subscription guidelines here.

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