Jill, what was your most awkward date like?
| S:2 E:3Dating sites can be overwhelming for anyone, but especially for those taking a chance on love later in life. Our story this week centers around one woman’s journey to find a new companion after a decades-long marriage.
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Krista Baum:
Hi, welcome to the Storyworth Podcast, we're glad you're here. I'm your host, Krista Baum, co-founder of Storyworth. On this podcast, we feature true stories written by Storyworth writers. If you're new to Storyworth, we help people write their life stories, the big stories, and the small ones.
Once a week, we send our writers a question to help inspire their writing. They reply to the email with an answer or a story that comes to mind. At the end of the year, we print what they've written into a beautiful keepsake book.
Every story written using Storyworth is private. But for this podcast, the writers volunteered to share their stories publicly with you.
[Music Playing]
Dating sites can be overwhelming for anyone, but especially for those taking a chance on love later in life. Our story this week, centers around one woman's journey to find a new companion after a decade's long marriage.
Jill Summerhayes, the author of this week's story, is here to give us even more juicy details about one of the strangest afternoons of her life.
But before we talk to her, we're going to hear her story read by voice actress Jessie Gill, as Jill answers the question: what's the most awkward date you've ever been on?
Jessie Gill:
Who doesn't love hearing an awkward date story? We all secretly delight in all the gory details of other people's dating ordeals. These kinds of stories usually involve a pair of 20-somethings fumbling to find love. But I can confirm the ups and downs of dating can strike at any age.
My own experience came after 40 wonderful years with my husband Stuart. We had such a strong, loving relationship. He did everything he could to make me happy. One of the hardest parts after his death from colon cancer was missing his company.
My daily routines were suddenly so solitary. I didn't like living alone, eating alone, going to bed alone, waking up alone. I missed having my companion joining me at the movies or dinners out, and at holidays and social gatherings. I also missed having a cheerleader by my side. Stuart was so supportive, offering me compliments and reminding me how loved I was.
We all appreciate affirmations like that, and without him, I felt a quiet void. I wasn't depressed. I could still laugh, share some fun times with friends, and keep a busy lifestyle, but something felt incomplete.
So, three years after Stuart died, I'd decided I'd had enough being on my own. I wanted to open up my heart again to a new relationship, but I was interested in something meaningful, more than the quick flings some local men seemed to think I needed. Despite my repeated refusals, some men never gave up.
So, I finally took matters into my own hands and turned to a popular online dating site. I pieced together my write up and attached a few photos of myself and winced as I activated the account. My profile went live. This was really happening.
Then the website's algorithm selected a few member profiles deemed compatible with mine. As I scrolled through my matches, I began to notice many of the men's profiles sounded the same, especially their descriptions of the ideal partner: “Must look good in jeans and a black cocktail dress.”
I rolled my eyes already beginning to question the process. I studied more of the men online. It was funny to notice their patterns, like the fact their descriptions seemed tailored to what they thought women wanted to hear.
I came across saccharin phrases like “I love long walks on the beat holding hands,” or “My ideal date is a romantic evening in front of the fire with a glass of wine.” When you've read the same line a dozen or more times across different profiles, you start to suspect they're just designed to attract women, rather than offer a genuine reflection of the person. These stock phrases were my cue to stay clear and click onto the next profile.
After a lot of waging, through lackluster profiles, I found someone promising. David seemed honest, direct, and sincere. I found myself smiling as I read through his information. He was interesting and thoughtful.
His photos offered a glimpse of a well-dressed man with a pleasing face and a friendly demeanor. It was so refreshing to find someone I could envision spending time with. I made the bold move and sent a quick message off to him and he responded.
We began swapping emails and discovered a few common interests. The messages flowed so easily, and I found myself perking up whenever I noticed a new message arrive from him. I was pleased to find good potential with David and wondered if it could lead to happy companionship.
It was such a gratifying feeling to form this new connection, and for it to be reciprocated. I cautiously shared my excitement with some of my close friends, but easy come, easy go. There was apparently a lot going on in David's life, and after a few weeks, he decided it wasn't the best time to meet and pursue a new relationship.
Disappointed, I moved on to other profiles and continued my search. I naively selected someone who bore some resemblance to David, my one who got away. His name was Bob, and he seemed nice.
I figured maybe I should settle for second best. I had a very pragmatic online dating strategy. No matter how good a man might look and sound online, actually meeting face-to-face displays the truth more readily than old photos and wordsmith descriptions can.
The meetup in person also offers a quick litmus test of whether or not there's real chemistry. So, after a few introductory emails, Bob and I arranged to meet at the local Butterfly Conservatory one Sunday morning.
I'd experienced dates before that were dead on arrival, the kind where we met for coffee, but had absolutely nothing to say with zero common interests to build on. It was difficult to invent an excuse to leave after a short time sitting in a coffee shop together, so I refined my strategy.
I suggested venues with more activity and distractions, and if the date was disappointing, it would hopefully, be less awkward than trying to extract myself from a coffee shop. The Butterfly Conservatory offered plenty of distractions and was only 20 minutes away from my home. If no interesting conversation developed, at least, we could wander around and look at butterflies and salvage the outing.
Bob was waiting in the parking lot when I arrived. He was sitting in the car. He described in the email a distinct older model Chevrolet. Let's just say he looked considerably more mature than his photos online.
Bob stepped out to greet me, and we were the same height, which was a surprise because I'm on the shorter side, but it wasn't a deal breaker in my book. At the gate to the conservatory, we agreed I would buy the entry tickets and he would buy lunch later on.
I suggested he hang up his leather jacket since we were after all, entering a hot solarium. His response was to pull his jacket possessively around him, announcing it had cost him $8 at Value Village.
He seemed especially proud of his jacket and mentioned it was a rare find that was too precious to lose. Maybe this should have been a red flag, but I ignored it. I have nothing against reused clothing. It makes sense, but it was a surprising opening statement within minutes of meeting each other.
Once inside, we sat on a bench surrounded by a range of lovely blue butterflies and tropical foliage, and made attempts at conversation. It went nowhere.
His first question was, “Would you mind if I continued to play chess online if we dated?” A second red flag, perhaps. But I was still trying to gauge whether this man might have long-term potential, and I aimed to keep an open mind.
I mentioned in my online profile that I love to travel, but when I brought up this hobby to Bob, he was taken aback that I would have any interest in ever leaving Canada. He'd never even owned a passport.
After a long pass, he said, rather reluctantly, “I guess, I'll have to get one then.” Conversation lagged, and Bob announced he wanted to snap some photos. Camera in hand, he took off down the palm lined walkway.
A few minutes later, I heard a commotion somewhere nearby in the conservatory. People were moving quickly, and I could make out someone asking urgently, “Sir, sir, are you alright?”
I swiveled around in their direction to see what all the fuss was about, and there was Bob completely passed out, sprawled on the ground. His eyes were closed, and he was pale as a sheet. His glasses and camera had scattered across the pathway.
My immediate instinct was to turn and run from the embarrassment of that scene. But I reasoned with myself. If I had been a total stranger, I would have stayed to help. And since I had invited him there, after all, I decided to do the responsible thing. I alerted a staff member for help and rejoined Bob.
People were congregating and offering support. A couple employees jumped in to assess whether there were injuries, and I remained by his side as he regained consciousness. We carefully escorted him out of the heat of the solarium to a chair.
Someone brought him water to sip and began to fill out an incident report. Bob was still woozy and bewildered. So, the staff person turned to me for his personal information. Being a regular visitor at the conservatory, they referred to me by name. “Jill, can you please give us his particulars?”
A sheepish expression poured over my face. I admitted it was a first date. And in fact, it was the first time we had ever met in person. I was flustered and even went so far as to mention we'd met online.
I had no idea what his full name was, let alone his address or health history. All I knew was that his name was Bob, and that he lived in a town over an hour away, and he enjoyed chess and shopping at thrift stores.
I noticed some amused looks among the people tending to Bob: “This is your first date?” Questioned a smiling employee. “I guess it might also be your last.” He grinned. But at that point, I was worried I'd be expected to drive Bob home, so I couldn't see the humor in the situation.
The staff insisted on helping Bob remove his precious leather jacket, and he was offered some orange juice and a muffin to eat.
20 minutes later, he had recovered enough to finally complete his own incident report. As the staff questioned him, some interesting details came to light. It turned out Bob had not slept the night before.
He agonized over the fact he lived an hour away from me and tried to imagine how he would navigate this long distance relationship. He was worried he lived too far to help me in my garden. My passion for gardening was featured prominently in my online profile. So, it seemed he had paid attention after all.
By the early hours of that morning, Bob worried about falling asleep and missing our appointment time. So, he drove directly to the parking lot where he sat waiting for three hours with no sleep, no breakfast, not even a coffee in his system.
He then walked into a hot house, shrouded in a leather jacket. The fainting spell made a lot more sense, and I was startled to realize how seriously he took our date. It added a new layer of pressure to our already ill-fated outing.
Once he fully recovered, Bob suggested we could go for a walk, but I strongly urged him to drive straight home while he was feeling better. I instructed him to send me an email letting me know he was home safe, and I advised him to make a doctor's appointment in the morning for a checkup.
We chatted awkwardly for a few minutes before he left: “You are a really classy lady,” he told me as conversation dried up, “I'm really looking forward to our next date.” I was stunned into silence. It didn't seem like the right time to mention the feeling wasn't mutual.
That evening, I sent an email thanking him for driving out to the conservatory to meet me. I took a deep breath, and then typed out the honest feedback, we did not seem to click. I was going to continue my online search for a more compatible match.
His breast response was, “What did you expect? Fireworks after the first hour?” I wanted to reply “No, but a spark would've been nice.” But I managed to refrain.
My daughter, Alison called that night to ask how my date went and retelling the ordeal sent her into gales of laughter: “Mom, you have quite the effect on men.”
Luckily, by then, I could see the humor in my story and the two of us giggled as I described my date to her in a somewhat unflattering way. I'll admit that experience is a favorite story among my friends.
It also became a running joke with the staff at the Butterfly Conservatory, who playfully teased me for months about the incident whenever I visited. It probably comes as no surprise, I decided to go offline after this encounter.
But first, I sent one last email to my first connection, David. I mentioned the comedy at the conservatory and my effect on Bob, hoping he might be able to relate to the sometimes arduous process of dating.
On a whim, I found myself typing out the words to David. I really enjoyed almost meeting you. I gave him my real name and invited him to reach out if his circumstances ever changed. In the meantime, he could Google me and find out more than he ever wanted to know.
When his response arrived, I found it sparked the same emotions his messages initially did. You might even call it the spark that was missing with Bob.
[Music Playing]
David mentioned he felt the same way and suggested we meet. Not long after, a relationship quickly developed. David and I have been together for almost a decade now.
On August 22nd, 2015, we were married, which was such a special day with all our grandchildren playing a role in the ceremony. So, the ending to my awkward date story is different from most, it actually led to lasting love.
David and I feel so fortunate to have found each other, even through our unusual trajectory. We've been enjoying love, laughter, and adventure ever since, and I'm happy to report he has yet to faint in my presence. And his two leather jackets did not come from Value Village.
Jill Summerhayes:
My name is Jill Summerhayes, and I live in Cambridge, Ontario in Canada, and I immigrated 53 years ago from the U.K.
Dave Morgan:
I'm Dave Morgan. I live with Jill in Cambridge, and I immigrated to Canada in 1946. I had my first birthday on the ship coming to Canada.
Alison Turner:
I'm Alison Turner. I'm Jill's daughter living in London. I've been here for just over 20 years.
Krista Baum:
So, Jill, how did you come to find Match? Like was that just the one that was the most popular or had you have friends that were using it? How did you come to find Match?
Jill Summerhayes:
I found it because I made the mistake of starting with a couple of free ones, which were really sexual hookups: “If you're free tonight, perhaps you'd like to see me” type of thing. And that's not what I was looking for.
So, then I went onto one that I had to pay for, and I researched a couple of them, and they seemed to have pretty good recommendations. So, that was the one I went on.
Krista Baum:
Well, I just love that this guy got there hours early. Like not only was it a sleepless night, but he like didn't eat anything and he was so worried about being late that he was like hours early. It is perfect.
Jill Summerhayes:
Yeah, yeah, yeah. He may have been a good guy, but didn't work for me.
Krista Baum:
Well, were you flattered?
Jill Summerhayes:
He was extremely complimentary, so it was a little embarrassing because I didn't want to tell him there's no way this was going anywhere.
Krista Baum:
Alison, did your mom mention that she was going to start dating on match.com?
Alison Turner:
My mom had done three years after Stuart had passed, traveling, just being extremely independent. She had indicated that she was missing a partner. We knew that she was going to go for it on match.com at 71.
Dave Morgan:
The background is that I had been on Match the previous year and I was trying to extricate myself from that relationship. Jill reached out to contact me, I kind of said, “Well, I'm busy right now.” So, that took some time because I think Jill reached out to me in January or early February, and we finally met in May.
Krista Baum:
Yeah. So, you were in the “it's complicated” phase of your relationship?
Dave Morgan:
Yeah, yeah.
Krista Baum:
Tell us about your first date.
Dave Morgan:
Yeah, let me start it.
Jill Summerhayes:
Okay.
Dave Morgan:
So, I told you I was trying to get out of this other relationship. This lady and I were going to go out to this auction. We went to a concert the night before, and I cannot remember what happened but after the concert, she got in her car and drove back to her house, and that was the end of that.
So, I wanted to go out to the auction sale anyway. So, I'm driving out to the auction and I sent Jill a text, “I'm going to be at the Christie Lake Auction Center. Then I'd be more than halfway out to Cambridge. Maybe I can pop up for a coffee.” And so, the answer was, “It's not worth meeting anywhere else, here's my address. Come to the house.”
Jill Summerhayes:
I just got back from the farmer's market, I'm wearing an old t-shirt, jeans, no makeup, no hair done. And I come in and within two minutes, he's at the door. So, he came in, which is breaking all the online rules.
We're talking maybe non-stop for two hours. As he went to leave, I asked him if I could have a hug. And he was quite taken aback and most embarrassed, but I was missing hugs, and he looked like the kind of guy that was huggable. So, I got a hug and I thought, “Oh yeah, okay, maybe there's something worthwhile here.”
Dave Morgan:
Things moved pretty quickly.
Krista Baum:
Yeah. So, what was going through your head for that week? Were you texting or was it like silence or what's going on?
Jill Summerhayes:
Emailing every day. Usually, first thing in the morning. One morning I sent a message to David saying, “I really miss you this morning or something. I wish you were here.” And he said, “Look in your driveway.”
And he had driven out to come and see me. So, hey, okay, that's it. If this guy does that, on the spur of the moment-
Dave Morgan:
Well, we were thinking along the same lines.
Alison Turner:
I think my mom always trusts her gut instinct. She knew, especially after having two not so great dates that there was potential with David.
Jill Summerhayes:
One of the things, Krista, which is not in this story, but which was a follow-up, was that David had association meetings in Denver and he was planning a road trip, and this was a few months after we'd met.
And so, he said, “Would you like to come with me?” And I said, “Sure.” And one of my daughters, she's the safety control officer, like, “Be careful about this mom. Maybe that might happen, mom, maybe ...”
Whereas Alison says, “Okay, kind of go ahead.” But this one, she said to my son, “Can you imagine that's the end of this relationship? Mom's getting in a car with this guy who she hardly knows driving for eight hours a day. She's going to have to pee every two hours and her arthritis will be so bad at the end of the day, she won't be able to get out of the car and she thinks this is going to be great.”
We had a great time. We traveled really well together. That kind of showed us. And somebody said, “Well, no, no, you can't tell from that. You have to go on a cruise together because when you're stuck in a cabin together, you'll know.” And we said, “Yeah, we're doing that next week.”
Krista Baum:
After two dates, you really hit gold. So, that's pretty good batting average.
Jill Summerhayes:
I think David had a few more prior to that but yeah, I hit gold after a couple. One of the things that we really enjoyed, Krista, was our wedding when we decided we were going to get married.
Krista Baum:
Tell me about it. How was the proposal?
Dave Morgan:
We go down to Barbados and Jill has some friends there, and we got invited to lunch at the yacht club, and I didn't know, but the bartender at the Barbados Yacht Club makes a really, really mean drink.
Jill Summerhayes:
Rum punch.
Dave Morgan:
Rum punch. And I had two of them. And I was hammered, and I had planned to propose at dinner that evening, and I could barely walk back to the hotel after lunch.
Jill Summerhayes:
David had been talking about buying a really fancy car that he had his eyes on, and he kept saying, “Maybe we could get …” And I kept saying, “No, no, no, we don't need a car like that.” But he hunted after this car.
We went up to a really romantic place for dinner. We're looking at the sunset, he brings champagne, we're watching the waves washing from the shore. He orders a bottle of champagne, although, as he said, he was a bit hammered already.
Well, David says, “I have something I'd like to say.” And I thought, here we go. This is the car. That car would be really important because da, da, da, da, da. And he says, “It would be really nice if we were to get married.” And then he proceeded with the proposal, and I was absolutely shocked. His grandson had lost both of his grandmothers.
So, he'd said to his daughter, “Do you think anybody has a spare grandma anywhere?” And he was, what, six, seven at the time. He had said to his mom, “Do you think this relationship with grandpa and Jill is going to go anywhere?”
And so, his mother relayed this to me. So, I took him aside and I said, “I don't know Seth, but if it does, you will be the first to know.” Once I accepted the proposal, I called Seth and Susan said, “Has grandpa proposed?” And I said, “Yes, but I have to speak to Seth.” And I said, “Your grandpa proposed last night and I accepted.” And he said, “A grandma.”
Dave Morgan:
We were staying at a little hotel in Barbados, and Jill used to stay there, and she knows the general manager. And so, she was so excited she had to tell somebody.
So, she went and told the general manager and said, “This is a big secret. I just got engaged and you can't tell anybody.” Well, we're sitting at the patio, and they've got a DJ and 10 minutes later, he says, “Will the newly engaged couple please come out for a drink.”
Jill Summerhayes:
I was afraid somebody might put it on Facebook and then all the family say, “Well, how come you didn't tell us?” That was expensive bill calling all those people from Barbados to tell them, but we did it.
Krista Baum:
Jill, how did you get started with Storyworth?
Jill Summerhayes:
My stepdaughter, Susan gave it to her father as a gift because her mother had died before she was interested in knowing their stories. And so, she wanted to make sure that her father had the stories written down before he died.
And I watched him doing this and I was so impressed. I thought, “Hey, I like writing. This will be a legacy for my children, so I will write the story.” And I loved doing it, and so many memories came flooding back. It was an excellent process.
So, once I'd done volume one, then Alison read it and said, “Well, there's a few things you didn't really answer, mom, but I have more questions for you.” So, she gave me a sheet of questions and I started on volume number two.
And it was a super thing to be doing during COVID lockdown everywhere because it kept me happy and occupied, brought all these memories back. I think Storyworth is one of the best things that you guys should be very proud of having started it.
Krista Baum:
Aww, thank you. Oh, you gave me chills because you know what? My dad died when I was young, and I actually invited his sister to Storyworth, and I really was shocked at how much I learned about my dad like his childhood that I would never have otherwise known. So, Jill I feel that.
Anything else you guys want to share about your Match romance and your awkward date?
Jill Summerhayes:
I mean, we could go on forever, but that's why I keep re-registering for Storyworth.
[Music Playing]
Krista Baum:
Thanks for joining us today. If you want to get started writing your life stories or want to give the gift of Storyworth to a loved one, head over to storyworth.com/podcast. And if you'd like one of your Storyworth chapters to be considered for the podcast, go to storyworth.com/podcast. In our next episode …
Narrator:
“I've got something to tell you,” she baited me (something exciting). I replied, “Yeah, like what?” She continued to hold my gaze across the breakfast table with a big smile on her face: “You're going to be a daddy.”
Krista Baum:
A story about a young man dreaming of fatherhood while preparing for the birth of his first child and what happened after a complicated delivery.
Storyworth is a production of Evergreen Podcasts, hosted by me, Krista Baum, and produced by Hannah Rae Leach. We get production help from Jill Greenberg and our mix engineer is Sean Rule-Hoffman.
We'll see you next time.
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