It didn’t take long to realize, that this person was not just another online dating prospect. THIS person was… different.

There wasn’t one big thing that jumped out, but several things—not unheard of or once in a lifetime, by themselves. But together, they added up, and started adding up very quickly, even before we had first met.

She wrote me first. Not unheard of, but in my online dating experience (at one point I counted 12 heartfelt, well-crafted introductory emails sent for every ONE response, of ANY kind), taking the initiative almost always scores big points on the “real” vs. “playing around” scale.

Then there was what she wrote, and what she wrote about. She wrote about what she could tell about me from my profile and about why she liked those things. She talked a little about things she liked, qualities she had that it seemed we might have in common. Even in just saying, “Hello,” she was making a connection.

OK, so, NOT a window-shopper. NOT a professional dater. Promising…

When she wrote, it was the beginning of the school year. My son had just started high school and my daughter was starting third grade. We had just gotten back from a good, but also problematic and VERY exhausting vacation. Work had kicked into overdrive, and then some. So, without really meaning to, I ended up testing her, by my response. Or, more exactly, by my lack of a response.

After a quick, “Thanks for writing, I’ll write more soon,” response, I, well, didn’t. Write more. Soon.

BAD internet dater!

Most people, myself included, would have gone, “Oh well. Met someone. Not really interested. Too busy. Whatever.” We LEARN (the hard way, if necessary) to have a thick skin. And to not get too invested in someone we don’t know, yet.

But, bucking conventional wisdom, 15 days after I said I’d get back to her, “tomorrow” (liar!), she “nudged” me.

“I know life with 2 kids gets very, very busy. I’ve been swamped, too”

OK, now I started thinking I was really on to something (or, someONE). The confidence to risk rejection, not once, but twice. But not overconfidence, arrogance or delusions of an instant relationship. (I’ve heard stories of angry emails sent by spurned suitors: “Why don’t you have faith in US?” After a few emails back and forth, pal, there is no “us.”) Instead, this was simple, calm, humble but confident… interest. Still wanting to see if there is any “there” there. Wow.

You can be sure it took me MUCH less than 15 days to respond THIS time. (61 minutes, to be exact.)

Dinner was on for the following week. During that time, we corresponded more. And “more” really describes it—more depth, more openness, more willingness to share and take risks and express feelings. But, a few days before our first date, there was even MORE “more.”

We were chatting on Google Talk. We had tried to schedule time to talk by phone, but between kids and work and chores, etc. (plus my daughter’s radar for any conversation she can listen in on), it just didn’t work out. So we had begun instant messaging regularly. She typed, “I know this is weird to ask you out on a second date before we’ve even had our first, but do you have any plans Saturday?” (Our dinner was scheduled for Friday.)

[Long pause on my end…] “What did you have in mind?”

Confident and healthy, or stalker in training? For an instant, I wondered.

“Well…” She went on to describe something that, frankly, sounded amazing. A guided walk along Portland’s waterfront called the “Blind Date Tour.” Designed to raise money and awareness around blindness and disabilities in general, the idea was one person wears a blindfold and must rely upon the other to be guided on the walk—around skaters and joggers and bicyclists and benches and cracks in the sidewalk. At the halfway point, the couple would switch the blindfold and the other person takes a turn at being “blind.” Participants would learn both how to lead and how to follow, understand a little about blind mobility from a first-person perspective, and explore Portland’s historic waterfront, all while raising money for a good cause and enjoying the company of their “date.”

Blind Date Tour poster

Provocative, even daring, I thought. I mean, I had never heard of a cooler, potentially sexier idea for any date. But a second date? The image of putting your trust in someone you barely know, and of them having to trust you, in turn. Of touching them—not in a necessarily sexual way, but touching them nonetheless. Wow. Talk about putting it right out there!

“The kids and I were going to go pick apples in the Hood River Valley,” I typed.

Pause. Must have seemed like the longest pause in history, poor thing!

“But we could do that Sunday instead. This sounds great!”

I swear I thought I heard her exhale all the way from my house!


Our first date was lovely. We talked about real stuff. REAL things; hard things; challenging things. I can tell you, as a widower, and especially a public widower, nothing says “credibility” like someone who cuts through the BS and shows they are interested in REAL. While evaluating the dessert choices at a spot down the street, she leaned into me in a way that was very sweet, not at all tawdry, but which absolutely got my attention.

We hugged goodnight. In a choice I may never hear the end of (in a loving, teasing way I totally deserve), I did not kiss her. I have never kissed on a first date, unless that “date” was actually the culmination of a courtship as opposed to the first time I actually met a person face to face. I think part of me didn’t want the person to think I was mainly interested in sex. Or that I was a player or a pursuer. I had also been burned by a dating relationship where an obvious, mutual physical chemistry had bubbled up on a second date, only to then be told, prior to the third date, “I’m not going to kiss you then, or any time soon, probably.” Oh KAY…

But after we hugged, I couldn’t let go. Literally. I held on to her hand for what seemed both a very long time and not nearly long enough.

The only reason I did let go was that I knew I would see her, and hold her hand again, tomorrow.


The weather was lovely. The event was everything you would imagine. We were, in fact, the only people anywhere close to actually being on a “blind date.” Soon after I arrived, the organizers said a few words, and we leaned into each other, irresistibly.

Putting on the blindfold

But it wasn’t all hearts and valentines. At the half-way point, she spoke to family members about a seriously ill relative. The news was not good. Real life has hard stuff, smack dab in the middle of the beautiful. I knew that. She knew I knew that. I showed her that I understood and would support her however she needed. I wasn’t going to run at the first bump in the road, and neither was she. Quite an amazing thing to realize on your second date in as many days.

Blind Date tour

Her touch was strong, but not clingy. I told her I sensed a strong, passionate nature, just beneath her surface. She chuckled, caught. (Months later, her adult daughter said to us, “Uh, are you guys trying to keep things a secret? ‘Cause, uh, you’re not doing a very good job of it!” How perfectly that statement would have also fit in that moment!”)

After I took my blindfold off, I no longer needed to hold on to her to move around, to avoid walking into a bridge or being run over by a bicyclist. But I didn’t let go. And neither did she.

What happened next can only be described as one of the best cases of bad luck being good, or making lemonade out of life’s lemons that I have ever experienced.

I made the mistake of recommending a restaurant to which I had never been. To say the service was poor would be an understatement. When we asked the server how spicy a dish was, she replied curtly, “I like things spicy, so I have no idea.” Worse though, was her attempt to keep us at arms’ length, literally. We had continued to hold each other’s hands since the end of the walk, and as we were eating our dinner, we held hands across the table. A lovely, romantic scene, you might think. But not if you have an Indian Cruella de Vil waiting on your table! At every possible opportunity (many of which seemed extremely forced), she would insist on filling our water glasses, or clearing our plates in THE way that would MOST disrupt our public display of affection. Now, keep in mind, we were not groping each other or making out. We were HOLDING HANDS. But, for whatever reason, she took it as her personal mission to break us up.

Much to the surprise of no one, it had the exact opposite effect. The door had not even closed behind us on our way out before I pulled her aside and kissed her like I meant it. Because I did. I really, really did.

To be continued…

[If gooey romantic stuff makes you wanna barf, you’d better grab an air-sickness bag or skip Part Two altogether. But you'll be missing the best part!]

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