Dating Scene(s)
Several months after my husband and I split in 2018, at the age of 62, I began to try my hand at dating again. My life and the world of dating, had changed drastically from the days of meeting someone in the supermarket (where my husband and I met back in 1985). Few of my friends knew anyone to recommend and most were married or coupled off themselves. It was my turn to learn the art of swiping.
Deb, my one single friend, created my first online dating profile on the Bumble dating app.
I love everything the city of Boston has to offer. You might find me sailing on the Charles (just learning), playing golf (always learning), or enjoying walks along the harbor. Could we share some discoveries or laughs? Hope so.
Deb threw in golf even though I only played with my sons (and my husband before he was an ex.)and frankly, could take it or leave it. “Men like golf,” she advised.
Then she taught me how to swipe. Left on those you’re not interested in. Right on those you’d like to get to know.
Man with no shirt on boat holding up large fish. Left
Man with no shirt on beach, arm around babe in bikini. Left
Man with no shirt on deck at barbecue. Left
Ex-husband. Left!
Not yet having found the elusive match on Bumble, I expanded my horizons and joined J-Date. That’s where I found “Zadie”, the affectionate name I called him to myself. It means “grandpa” in Yiddish. I think my friends were so excited to see me go out for the first time that they overlooked his photos which to me screamed sweet old man more than hottie.
“But look at that picture where he’s holding up his hand to show off his fitbit,” my friends pointed out. And then Deb explained, “The first date is like the first pancake. It takes a few before you get a good one.”
Zadie and I met at Legal Sea Foods. I went nuts trying on different outfits before landing on a black pleather jacket and black skinny jeans. I thought I looked hot. “You’re even more beautiful than your photos,” said Zadie upon seeing me in the restaurant lobby.
I’ll admit it, that was a boost. I wasn’t sure how attractive I’d be to anyone after the humiliation I experienced in my marriage. At this point, I didn’t care who said it. It was nice to hear, even from Zadie. He was a widower of about six years. He was proud of his life and his career and spent a fair amount of time extolling the fortune of good investment decisions. I was a mature woman having a high school experience. Half of me was listening to what he was saying and the other half was thinking ahead to what comes next when dinner ends and we part ways. Do we hug? Do I kiss him on the cheek? Do I just say thank you and walk back to my apartment? (the restaurant was a short walk from my building). As we got up to leave, he asked if he could see me again, I said sure. We exchanged a brief hug — though it was clear he would have liked more, and we parted ways.
For our next date we played golf. Maybe Deb was right after all. I know, it wasn’t my thing. But it was a chance to see how energetic Zadie really was. I out-hit him.
After the game, we drove to his place to kill some time before dinner nearby. I was a little nervous. I had to change for dinner and I was pretty sweaty from the game. It would mean taking a shower in his home. He lived in a beautiful modern townhouse filled with interesting artwork and craft pieces. It was plenty big and he was a gentleman, offering me a bathroom and bedroom to change in that was far from where he would be doing the same. After I was dressed there was still time before we had to leave for dinner. We sat in the living room on his white leather sectional to talk. “Do you cook?” “Yes, I cook.” “Good. If you lived with me, I would take good care of you and you can cook and keep up this beautiful house.” The poor guy just needed a traditional woman in his life. Not me. I made it through dinner and when I got home, I wrote him a Dear John letter and hoped it would let him down easy. He was my first pancake.
Back to swiping.
Over the next year and a half, I dated a few more times. Dinner at a sports bar with a drilling engineer who was disappointed I didn’t drink a lot, a walk with a retired technical expert in satellite radio who, on our date, told me he was sapiosexual. Was I supposed to discuss quadratic equations over dinner? I kept swiping.
I soon learned that online dating was teaching me what I didn’t want. A process of eliminating the pancakes until the best one showed up in the pan. I didn’t want to take care of someone else’s laundry or cook their meals. I didn’t want to have to get drunk to enjoy his company. I didn’t want to have to prove my intelligence.
Scene II: Bookworm — February 2020
Shortly before the world shrank to the size of my 750 square foot condo, I met the ideal candidate on Match. He was a journalist turned content marketing professional, Jewish and my age. He was taller than me with a shock of dark hair, longish around the ears and at the back of his neck. He walked slowly and deliberately with a little sway in his gate that created a slightly effeminate style to his steps. He dressed simply in “daddy” jeans with pressed flannel shirts buttoned high on his neck and down to his wrist. An odd choice that seemed a bit formal for an otherwise casual almost “college-student-like” wardrobe. But his education and experiences made for interesting conversation and the chance to explore unique settings for our dates. An avid reader, he loved American history.
For our fourth night out, I booked an event at the King’s Chapel in downtown Boston, established in 1686 as the first Anglican congregation in New England. It was an evening tour of the crypts beneath the church where some of Boston’s most notable and notorious were buried. There, in the dark, ducking beneath the historic wooden beams and around the stone walls, I took his hand. I wanted to see how it would feel. I was hoping for stomach butterflies but felt none.
By our next date, in February, the pandemic had begun and though we weren’t wearing masks yet outdoors, we were told to stay six feet apart. I cut a string of yarn to size and we took a walk along Boston Harbor holding the strand taut between us, at times looking like we were each other’s dogs. By all accounts, he should have been the one. And I really tried. But I had to be honest with myself, I just wasn’t feeling it. Another discovery, I didn’t want to have to force my feelings just because everything was good on paper. So, after our fifth date, I politely cut it short. It felt like I was giving up a precious roll of toilet paper just when everyone else was hoarding them.
Scene III: Deputy Dawg — August 2020
After nearly an entire summer avoiding dating altogether, I ventured out once again. This time connecting with a friendly fellow who wrote on Match.com, “How about an ice cream some time?”. It seemed so appropriate and courageous on his part. Why not just meet for ice cream rather than have a bunch of small talk over the app’s texting feature? He would be wearing a blue polo shirt; I would be wearing yellow stripes. We would meet just outside the South Station subway stop for a walk along the Greenway, a jewel of a city park covering a major highway that was submerged during the Big Dig. I recognized him immediately with those “Deputy Dawg” eyes peering over his mask. I waved hello and we started our walk.
“Never been here,” he said. I was surprised. “You grew up in Dorchester (a neighborhood just a few subway stops from where we met) and you’ve never been to the Greenway?”
“Nope,” he said matter-of-factly. “I’d leave my house to get up to school and then take the train right back. Never stopped anywhere in-between.”
So, I played tour guide as we headed toward the Starbucks. He was chatty. He offered that his dad had a fuel injection repair business along the harbor which serviced lobstermen’s boats. He spoke fondly of his dad who lived in the apartment upstairs from the repair shop.
“Do you live with your dad?” I asked. “No,” he offered. “I live in a rooming house. But if I ever had you over for dinner, we’d eat at my dad’s place.” That was the first hint that we might not be the perfect match. He was nice enough though. He offered to pay for my iced tea and we proceeded over to the benches across from the shop. “This pandemic has really screwed me up,” he said as he removed his mask, “I’d have my teeth by now if it weren’t for COVID.” Then he smiled as he sipped his iced coffee. I suddenly remembered a meeting I had in a half hour and cut things short. More discoveries — I’m open-minded, but I need someone who’s traveled further than his commute to school.
After that last date, I deleted every dating app on my phone, hid myself from all those that I couldn’t entirely get out of and decided to buy a condo. Huh? If I wasn’t going to put energy into finding that partner to share my life with, I sure as hell wasn’t going to sit still where I was. I was renting an apartment that I knew I wouldn’t be able to afford forever and it occurred to me that it might make sense to own something instead. It felt great to turn my attention to setting up my future, with or without a “best man”. By the fall of 2020 I had found a great place, affordable with a beautiful view of the harbor. I’d have to downsize for a third time and do my laundry in a basement room shared by the whole building. But it was worth the sacrifices to not have to move for another 20 years or until I start forgetting to turn off the stove, whichever comes first.
Scene IV: Mr. Rotterdam — November 2020
By winter, with the move behind me the “lonely’s” were setting in — that feeling you get when you wake up day-after-day to an empty 750 square feet of space, a quiet phone and slow email box.
A well-meaning friend suggested I try Tinder Gold. Ugh I thought, Tinder? Really? I’m 64. I’m no cougar and I’m sure as hell not interested in hook ups. At least that was Tinder’s reputation. But the “lonely’s” were calling and the pandemic wasn’t going anywhere. Vaccines were coming but it would be months before I’d be eligible. What did I have to lose? It wasn’t like there were other options out there.
Tinder Gold was like nothing I’d ever experienced before. After three days I’d accumulated 94 “likes”. Where did all these men come from?
I began searching the inventory. That’s when I found Mr. Rotterdam. An attractive guy slightly younger than me but mature looking, with that day-old scruff that makes a man look rugged but cool. He was a civil engineer originally from Rotterdam with a moving story about losing his best friend to COVID. His stories were thoughtful and pensive. I was touched by his grief. We chatted within the Tinder app for a couple of days before texting over our phones. I made the cardinal sin of giving out my number, but didn’t realize it at the time. Once we were off the dating app, I became part of the “wild west” where catfishers and scammers abound. Mr. Rotterdam was most definitely a catfisher. His texts grew more and more extreme. “You are so sweet. I love your messages. You remind me of the kindest person I ever knew. I think I’m falling in love with you.” We hadn’t even met yet. And every time I asked if we could, he put me off. “We’ll get to that,” he’d say. “I feel like I’ve known you all my life.” I was getting scared. This guy had my name and my phone number. I was in dangerous territory. I stopped texting, blocked his number, hid my profile and reported the incident to Tinder. Ladies, pay attention, the dating app can’t do anything for you once you leave the app and have interactions on your own phone. Another discovery. I don’t want to be scammed.
After the incident with Mr. Rotterdam I gave up on online dating entirely. Between the ongoing pandemic and winter in New England, it was highly unlikely that love would come along any time soon. I spent the next five months dealing with “the lonelys” by taking online classes, Zoom calls with friends, and periodic COVID tests to be able to visit with family now and then.
The advent of warm spring weather, vaccines and the prospects for gathering renewed my energy for dating. But it was time to try something different. Today’s matchmakers were getting a PR boost from the likes of Patty Sanger’s Millionaire Matchmaker on Bravo TV. Maybe plunking down a few thousand dollars was the way to a man’s heart after all. Or at least a way to make sure only the truly lonely would get thrown my way. I decided to take my chances.
Scene VI: Matchmaker matchmaker, make me a match
I met Suzie at her office in a large office park north of Boston. A bookcase of family photos, seashells in a glass and funky tabletop crafts stood in a bookcase opposite her desk. There was a credenza behind her topped with files and more nautical decorations. After a few social niceties, she asked, ‘Hi, I’m Suzie. You must be Andi.” “Yes, hi,” I replied. “So, tell me what brings you to hire a matchmaker?” “The search for true love and the promise of quality inventory.”
We went through my interests and lifestyle, and a bit about my background. My divorce, my kids. And then the all-important, “What are you looking for?” With the confidence of an educated consumer, I said “An honest man who is energetic, financially secure and interested in a serious relationship for the next chapter of their life,” I said. “I bet you hear that from all the girls.”
I couldn’t imagine she had ever heard anything else. I deserved at least that much I thought. But describing my ideal partner, that was going to take more time. I wonder what she would have done if I said I’ll only date a sea captain. Given the décor, that might have been easier. Suzie walked me through the six-page contract which offered unlimited matches for up to six months. “Where do I sign?”
Scene VII: Plaid Giant
A couple weeks later, Suzie sent a photo of my first match. He was 6’4 to my 5 feet. Slim with silver hair and an attractive matching goatee, standing in a black shirt and leaning against a brick wall. Kinda sexy. After spending the winter in a dating desert, I was ready to venture out. I told Suzie I’d accept the match.
His first call came while I was at the tailor getting a pair of pants shortened. We both laughed. A pleasant man in his 60’s, he had a high-tech sales position and a 13 year-old daughter from his second marriage. He suggested we meet for a walk around Castle Island in South Boston the following Sunday.
With outdoor masks no longer required, I was happy to put on make-up again and chose a form fitting sleeveless top with jeans and sneakers for our date. I looked good and felt good. After spending the winter alone, it was nice to be meeting someone entirely new even for just a couple of hours.
When I got there, I found a perch on a hillside under a shade tree across from the main parking lot to watch for him. I was sure I’d see him high atop the crowd where the air is rarefied. I texted my whereabouts so he would find me too. The place was packed. Little kids running around slurping ice cream on their scooters, parents calling their names twirling on the sidewalk hoping a constant 360 turn of their head would spy their little ones soon enough, and lovers with blankets walking arm-in-arm headed for the grassy knoll at the base of the fort. And then I saw a giant man wearing a plaid bucket hat, shorts and sneakers, head up the hill to my left. With just one of his strides he was a half-mile away. No way to catch him without twisting an ankle. Then my phone rang.
“Hey, I’m here. Where are you?” “I think I saw you,” I said. “Are you in a plaid hat? Come back down the hill and I’ll head toward you.”
And so our meeting dance began. Me stretching my neck to the sky and him walking with eyes down looking for the top of my head. When we finally met, he bent down while I lifted onto my toes and we exchanged an appropriate hug hello. Let the walk begin.
Though height was never a major criterion for me, I realized it was difficult to make eye contact while we walked. With a bench in sight, I suggested we sit a while. Unfortunately, it made little difference as Plaid Giant pretty much gazed off at the ocean straight ahead. He was a nice enough guy, but clearly not interested. The big tip off came when he said he’s likely to retire to Costa Rica within the year. Another discovery. I want to be with someone who wants to be with me, locally.
Scene VIII: Mr. Pickle Ball
A couple of months went by before my next date. A friend introduced me to a single guy my age whom she met playing pickle ball, the game Alex Beam, the Boston Globe columnist called “the shuffleboard of racket ball”.
Mr. Pickle Ball and I went on two dates and frankly, I liked him a lot. He loved wearing hats. A baseball cap on our first date, a straw Stetson on our second, which he left behind at the restaurant because I asked to see what he looked like without his hat and then he forgot it on the table. We walked back for it and extended our stroll to end the evening. We had so much in common. He loved films and reading, travel adventures and hiking. He had two grown children, one in the same city as one of my sons. I imagined us travelling together to visit our kids some day. He had smiling eyes and a silver beard and mustache, a friendly face. He was energetic, adventurous, easy-going and someone I thought I could really hit it off with.
But a few days after our second date he called to say that as much as he enjoyed our time together, he just wasn’t feeling it romantically. For all the times I “just didn’t feel it”, the table was turned. I was hurt, I felt rejected. What could I say? “I’m sure your travel partner is out there somewhere. Good luck to you.” “You too,” he offered. And that was that. I hung up the phone and let myself tear up a bit. It stung to be sure. I started to wonder if I just wasn’t young enough or thin enough or whatever enough to be attractive to Mr. Pickle Ball. But I quickly shed those notions and replaced them with the sad reality that my search simply wasn’t over. That romantic attraction can’t be manufactured or controlled. It either happens or it doesn’t.
I wish I could end this story like a fairy tale –
I was swept off my feet by the perfect guy who loves me for who I am, laughs at all my jokes, thinks I’m beautiful even after a sweaty workout, etc., etc., etc.
But that’s not how it goes. It’s weird knowing what I’m looking for but having no idea where to find it. I’m a little frightened that I may never meet that special someone. But I’m not giving up just yet. One thing’s for sure, the journey keeps me focused on staying fit, exploring new experiences and meeting new people. At 64, that’s not so bad. And maybe, just maybe, someone is out there taking a similar path. I just hope by the time we come upon one another I’ll remember what I was looking for.
