My Wingman Was 4-Year-Old — 'How My First Date As A Widower Turned Into A Table For Three'
When a widowed dad’s childcare plans fall apart, he turns an awkward situation into an unforgettable one.
cottonbro studio | Canva ‘Sorry to bother you. I hope your daughter’s chickenpox clears up real soon…’
I quietly swore under my breath, placing the phone back onto its receiver. I had to keep my voice down because my four-year-old son Brendan was nearby in his room, drawing in his coloring books. Still, after receiving similarly disappointing news in one phone call after another, my childcare situation had become seriously desperate.
I wracked my brain, trying to come up with a Hail Mary solution. But with a growing sense of resignation, I knew my options had dwindled down to a single, previously unimaginable choice.
Brendan was sprawled on his bedroom floor, coloring quietly, blissfully unaware of the preposterous evening that awaited the two of us. I quickly went over to his closet, carefully picking my way through the 64 Crayola crayons scattered around the floor. My eyes fell upon the light blue seersucker jacket and short pants his grandmother had recently bought him for Easter.
With a sigh, I decided that would have to do. I bent down to grab the new saddle shoes that went with this ensemble and called to him over my shoulder:
‘Hey, buddy — how about you run to the bathroom and brush your teeth extra quick? You and Daddy need to be downtown for a date in an hour…’
It was the summer of 1996. I’d recently turned 30, and had spent the last year raising Brendan on my own after my wife suddenly passed from a severe food allergy.
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Earlier that day, I was in the Philadelphia Criminal Justice Center, prosecuting cases along with another assistant district attorney during our three-month assignment to that courtroom. My partner was handling a specially assigned case scheduled for the afternoon involving a woman who’d been flown up from Nashville to testify against the man who robbed her in north Philly the previous year.
Her name was Gretchen, and she’d since relocated to Tennessee for work in the months between the defendant’s arrest and the trial date. She waited out in the gallery with a slight look of unease among the dozen or so other witnesses whose trials were also scheduled that day.
Gretchen and I chatted often throughout the morning during my breaks between cases. At first I’d simply intended to make polite small-talk. But I soon got the sense she was interested in continuing to chat further.
She later shared that our ongoing conversation helped take her mind off the prospect of having to testify later in the day. She was charming and funny, and I found myself more and more intrigued by her the longer we spoke.
Over the course of the morning, the defendant’s attorney had been trying to work out the terms of a guilty plea with my colleague, which would make the afternoon trial, and Gretchen’s testimony, moot. The terms of the plea were 99% worked out, but hadn’t been fully agreed upon by the time the judge announced lunch recess. On an impulse I asked if she’d like to join me to get something to eat during the break.
The fact that I was interested in meeting anyone came as a surprise.
My grief in the aftermath of my wife’s sudden death had been tremendous, but I’d quickly suppressed it in order to focus on balancing my new role, raising Brendan as a single parent with the demands of my full-time job. I hadn’t even been remotely thinking about meeting someone during that time.
At lunch, the conversation continued to flow easily back and forth. I hadn’t mentioned anything to Gretchen yet about the fact that I was a widower with a young child because in my experience, people often became very emotional upon first hearing about my and Brendan’s situation. I didn’t think it was fair to drop upsetting news like that shortly before she might be called to testify about the night she’d been robbed at gunpoint.
The defendant did wind up pleading guilty that afternoon, which meant Gretchen would soon be formally excused from the courtroom. We made plans to meet for dinner later that evening at a popular restaurant at 17th and Lombard called The Astral Plane.
She headed off across the Walt Whitman Bridge back to her parents’ home in New Jersey, where she was staying until her return flight to Tennessee the next morning. Before she left, we exchanged the landline phone numbers for her parents’ home and my house. I spent the rest of the day in the courtroom, trying the remaining cases on the docket.
I hadn’t been particularly concerned about arranging a babysitter while I was in court because Brendan’s grandmother lived nearby and was always happy to watch him, even on a moment’s notice.
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But as it happened that night, she had tickets to the theater. It turned out that each of the half-dozen babysitters around our neighborhood whom I called had plans of one form or another as well. I ran through every conceivable person I could think of, including the parents of some of Brendan’s playmates from pre-K, and then reluctantly tried to reach Gretchen at her parents’ house to explain why I needed to cancel our dinner plans for the evening.
Her mother answered the phone and explained that Gretchen had already left for the restaurant a little early in case there was heavy traffic. Technology in 1996 was very much analog, and it would still be 2–3 years before the digital age brought personal cell phones to widespread use among the general public.
At that time, they were a pretty impractical luxury item for most people — ungainly to wield and ridiculously expensive. I tried calling the restaurant to leave a message for Gretchen, but the hostess had too much trouble hearing me over all of the noise and hectic activity during the dinner rush.
So, at that point, I was faced with two equally unpleasant options.
Either I remained home with Brendan while Gretchen waited alone in the restaurant, thinking I’d blown her off after she’d driven for close to an hour and paid money for bridge tolls and parking to get there. Or I could just show up for our date at this intimate, romantic restaurant with a previously unmentioned four-year-old dressed like Richie Rich in tow.
This scenario was not exactly how I’d pictured my very first return to the dating scene. But since I was the one who’d set these events in motion, there was only one choice to be made. I buckled Brendan into his car seat, popped a Barney & Friends cassette tape into the car stereo, and we were off to make our 8 o’clock reservation downtown.
As I drove, I reflected on how it was somewhat comforting to have a wingman with me on my first first date in over six years. Granted, it would’ve been preferable to have brought one along that didn’t require the use of a booster seat.
I was hoping for the best but preparing for the worst as Brendan and I walked inside the restaurant, with him holding my hand, trailing slightly behind.
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As it turned out, I had nothing to be worried about. Gretchen was already seated at the bar by the time we arrived, and while her eyes widened in surprise when she first saw the two of us enter, they became slightly misty once I apologized and explained the whole situation to her. After a quiet moment or two passed, she told me she completely understood and knelt down to say hello to Brendan with a big, warm smile.
Our waiter, on the other hand, was visibly nonplussed. His reaction was understandable — the Astral Plane was well-known at the time as one of Philly’s more eclectic and intimate restaurants.
The soft candlelight illuminating the rococo furnishings and white silk parachute draped across the entire ceiling exuded a single, unmistakable mood: romance. It was decidedly not the sort of place where chicken nuggets had ever been featured on the prix fixe menu.
In fact, it was not the sort of place that had envisioned booster chairs as part of its seating plan, either. Two thick Philadelphia Yellow Pages stacked atop one another on Brendan’s Queen Anne chair did the trick.
Gretchen was wonderful and took everything completely in stride, and made a point to say how handsome Brendan looked in his fancy suit. I appreciated her effort and graciously refrained from pointing out there had not been much choice for a suitable alternative, as all the remaining clothing in my son’s wardrobe prominently displayed either Barney, Elmo, or permanent juice stains.
I have to say Brendan was on his best behavior that night. He could be a pretty finicky eater back at that age, so while I may have been pointing to the ‘Linguine with Sun-Dried Tomatoes’ in the menu as I placed his order with the waiter, I made sure to refer to it out loud as just plain old “spaghetti.”
Brendan’s table manners were even better than I could have hoped for. True — he did begin to build a little castle out of the sugar cubes he discovered inside the sterling bowl at the center of the table, but I decided to let it slide because at least that activity held zero danger of anything breaking, spilling, or staining, which in my book I considered a win-win-win. The fact that I had to drink my coffee black that night was a small price to pay for keeping him quietly occupied and the fancy tablecloth unblemished.
There was one minor incident before the evening was over. Midway through eating our entrees, a waiter approached the adjacent table with a four-tiered dessert cart, laden with fancy and decadent offerings.
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Brendan was transfixed as he watched each diner pick out the dessert of his or her choice. After everyone had made their selection, the waiter began to head off in the opposite direction toward another table in the next aisle. Brendan placed his hands squarely on the table, stood upright on top of the phone books, shot his finger toward the retreating cart, and declared, “I WANT CAKE!” in a voice that rang throughout the dining room with impressive volume for a four-year-old.
Gretchen burst out laughing, and it was all I could do not to join in. I quickly shushed Brendan and sat him back down on top of his throne of Yellow Pages and told him that he could have cake as long as he behaved and finished up the rest of his linguini… err, spaghetti. Fortunately, the rest of the meal went by without further outburst, and Brendan earned every bite of his cake as a reward — even if the sleeves of his jacket wound up sporting brand-new matching dark chocolate stains.
As it turned out, my tie now featured a noticeable splotch of duck demi-glace, so who was I to judge? We walked Gretchen to her car, and she smiled broadly. She thanked the two of us for a lovely evening.
She gave us each a kiss on the cheek, and then Brendan and I headed off back to our house for a long-overdue bedtime story. All in all, I couldn’t have asked for a more perfect night for my impromptu return to the dating scene.
It’s been twenty-eight years since that dinner — Brendan is now 32 and just moved to a neighboring town.
He’s been in several relationships over the years but isn’t seeing anyone at the moment. I expect it won’t be long before he starts dating again. I’ve been thinking maybe a little karma might be in order the next time he goes out on a first date.
I could tag along with him, sporting a spiffy new seersucker suit, prop myself up at the table with some phone books, and build something fun with the condiments while he and his date engage in small talk. The only difference would be that since I’d still be the parent, I could order dessert even if I didn’t finish all my vegetables.
As a matter of fact, please excuse me for a moment while I step away from the keyboard, as a very important thought has just now occurred to me: I WANT CAKE.
Thomas McPherson is a writer and attorney in the Pacific Northwest. His essays on Medium delve into his experiences as a husband, widower, single parent, oldest child, and lawyer with poignancy and humor.