I’m going to make it easy on you, she said. And then she broke up with me

I got the feeling Allyn was "all in." But was I?
(Maria Picasso / For The Times)

Nine months had passed since my ex and I had separated. It was time for me to put myself out there. I was single, healthy, loved to dance, had a good job … this would be fun. I wasn’t dreading the prospect of taking a dive into the dating pool, I was looking forward to it.

I had just begun to dabble in online dating when I came across her profile on OkCupid. Intrigued, I reached out, which led to several friendly conversations. Turns out we were both from New York before moving cross-country to Los Angeles. We both enjoyed happy relationships with our adult children and had similar political views. Our values were lining up nicely. And, wow, she genuinely laughed at my attempts at humor. That was heady stuff. It didn’t hurt that I thought she was attractive.

We decided to meet, not the easiest of tasks since she lived a good hour and 15 minutes away, without traffic, in Rancho Santa Margarita. Although she was geographically undesirable, I wasn’t going to let that deter me. Even though my sample size was small, I had done enough dating to realize that meeting the right person would not be easy: My early naiveté about how easy online dating would be had quickly given way to reality. But I felt an instant connection to Allyn. Maybe it would be different this time.


I told my dates upfront: I’m in it for the fun, not the long-term.

Oct. 26, 2019

A convenient opportunity to meet presented itself as good friends of hers were celebrating a birthday not far from me. She agreed to meet me at my condominium in Pasadena before heading to the party. Her daughter had been apprehensive. “Like, really, Mom, you don’t meet a new guy in his apartment on the first date!” But she did.

Allyn would later say she was trusting her intuition and felt she knew me well enough from our phone conversations. (It must have been all the time I spent talking about my daughters that did it.) As she stood at the entry gate to my condo complex, my eyes took her in. Yup, she looked like her pictures, whew. (I had already experienced the disappointment of people not looking like their online profile.)

She would later tell me how aware she was that I was looking her up and down, but she liked the subtle expression of delight that crossed my New Yorker’s can’t-hide-it face. And I thought I was playing it cool.

I was divorced, my daughter was off at college, and I came home to an empty house every night. Was I destined to be alone?

Nov. 9, 2019

That night we went to the birthday celebration. I tried my hand at square dancing. Epic fail. The do-si-do instructions befuddled me. She good-naturedly laughed at my clumsy moves. When the evening came to an end I walked her to her car. As she sat behind the wheel, I reached in for a goodnight kiss. Too soon. She shyly pulled away. I saw a glimpse of giddy innocence in her beautiful brown eyes, and I was charmed.

We gave it a go. One weekend we’d meet up at my place, the next weekend at hers.

Things were proceeding fairly well, but then the emotional reality of it all gradually set in. I got the feeling Allyn was “all in.” But was I? It crept up on me like a silent killer and began to chip away.

Was she really right for me?

Instagram was right: Keeping a relationship a secret can sometimes be just what that relationship needs.

Oct. 19, 2019


I admit it. I started picking at what wasn’t right in the relationship and losing sight of what was.

I felt myself growing distant.

She felt it coming on.

We attended her friend’s wedding in Camarillo. I was there with her, but I was vacant.

She understood I had already left the relationship.

A few days later, she called me. “I am going to make it easy for you,” she said. “I’m going to let you let me go.” Just like that, it was over. There was no anger. She understood what I was going through. She had been divorced for over a decade and had been in a few relationships since. And I was just coming to realize I wasn’t ready to be in a committed relationship just months after the end of a 23-year marriage.

I was simultaneously sad and relieved.

I understand not unloading all your personal baggage on the first date. But by date No. 2? That’s the time to say: ‘By the way, I’m married and have three children.’

Oct. 12, 2019

Eventually, I went back online and started dating — in quantity. I joined three sites. I was a dating force. It was all entertainment to me. I found something of interest in nearly every woman I went out with. It was a fun ride for a while. Most of my dates were one and done, a few lasted to date three, a few more made it past the two-month mark. I lost track of how many dates I had been on.

As the years passed, I would occasionally think of Allyn. I wondered how she was doing. Was she a grandmother yet? I kept my distance.

Out of the blue one year, I sent her a text wishing her a happy Mother’s Day. She didn’t know who sent it. After years of not hearing from me she’d removed me from her contact list.

After another text identifying myself I half expected to be met with cold silence. Or blocked. Instead, I got a friendly “Hey, how are you?” In the years since our breakup, she did become a grandmother. Pictures of her grandchildren were enthusiastically shared. Her energy was warm and welcoming. Our conversation continued down a path that felt familiar. Had more than five years really gone by since we last saw each other?

I suggested we get coffee sometime and catch up. During our conversation, I had mentioned briefly that my children were going to be in town in the coming weeks.

A few days later, she read about a chalk art festival in Pasadena and sent me a text suggesting my kids might like to see it. The dates didn’t work out. The kids would be gone by then. Somewhat impulsively, I asked if she would be willing to drive up and see it. “Uh … well, OK.”

I would learn later that she didn’t sleep a wink the night before.

As Allyn once again approached the gate outside my home, neither of us knew what was in store. But as we peered at each other through the metal barrier, five years melted away. What was familiar was also new. What exactly was going on?

Against all odds, we rediscovered each other at the gate where it all began.

When she stepped through the gate, I hugged her. She didn’t resist.

That day we walked hand in hand to the chalk festival. Two years and three vacations later, we are still walking hand in hand. We still divide the weekend driving. And the only baggage I pack these days is filled with clothes.

The author recently retired as vice president of marketing at the California Science Center.

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