I Found the Best Dating Hack as An Older Woman

Why it’s easier to play the game in my 50s

Photo by LollipopPhotographyUK on Pixabay

I’ve had a heck of a time finding a love match for the past nine years, the longest stretch I’ve had without sex or a significant other. With ample time to work out the kinks, I thought I would’ve met someone ages ago.

To connect with someone and fall deeply in love, hopefully living out our days together, has been my lifelong dream.

I’ve only had a handful of serious relationships, and I’m not getting any younger.

Am I running out of time to do what I consider one of the most significant experiences of my life?

I swiped left on thousands of people on dating apps. I only met one man and one woman, neither of them compatible with me or each other.

I’ve warmed the right side of the bed every night, and it’s starting to show with a rather prominent dent. If single life continues much longer, I might have to even it out by switching to the left for a while.

Revisiting old flames and making friends turn into previously unexplored love interests hasn’t worked. Although they looked promising on the surface, nothing came to fruition.

I wrote dozens of stories asserting I would never find anyone on a dating app, especially a cis man. After one too many fishing or four-wheeler pics and “no drama” in their bio, I was over it.

Nor would I find a date in all of Oregon, since there are too many bearded white guys driving monster trucks with MAGA stickers on every other block. No thank you, Mr. Right Wing. This queer single mama on government assistance is not your gal.

I had no luck with younger men, older women, or at Trader Joe’s, where I held high hopes of meeting my soulmate.

I resigned myself to being alone until I croak.

Back then, which was two weeks ago, I thought I was destined to be a crazy, childless cat lady when my kids moved out. My cats would eventually die, leaving me to live out my days utterly alone until a neighbor finds me in my purple velour pajama pants cold and lifeless in my unevenly indented bed.

I would become a trope. An old spinster hag, useless because I never married the right man. I couldn’t even find a nice butch lesbian divorcee with whom I could snuggle in front of my nonexistent fireplace.

Dear readers, I hadn’t planned on having so much solo sex or none at all in my 50s or delaying travel and higher education because it costs too much on a single income. I hadn’t intended on sleeping alone for this long.

I had no intention of bypassing a lasting, committed relationship. I was supposed to get married at least once this time around, damn it.

I want a partner, so why was I not finding one? Was I missing some new hack I hadn’t yet seen on TikTok?

Trader Joe’s for the win?

Although I’m a homebody by choice, I enjoy being a social butterfly when given the chance.

Because I seek out friends when in public, I look forward to grocery shopping. In between my left swipes and dodging inappropriate sexual comments online, I shop for strawberries and kombucha at Trader Joe’s while chatting up the staff. I’ve made friends with a few folks there and don’t feel lonely by the time I finished what most think of as a chore.

I’ve shopped at TJs for over 17 years, worked there once for two months, and have always had an excellent shopping experience.

A while ago, I started thinking I’d probably meet my match at Trader Joe’s. It made sense to find a connection at a place I love. I shared this with a few people here and there but recently went quiet about it. I was busy manifesting my first mate at my favorite grocery store.

After years of unrequited attractions as recent as two years ago, I finally found a responsive person.

We met years ago, but I hadn’t seen him in a while. I found him on Facebook and thought, hey, I know that guy. I saw from what he posted that we seemed to have shared values.

One day, out of the blue, he revealed he had a huge crush on me. Oh my, I blushed.

We started messaging. Everything we talked about synced up. He was enthusiastic. It’s been a long time since I got that kind of attention. It felt pretty nice.

I thought, did I just call it? Have I been right all along? Is he the one I’ve dreamed of meeting and already had a glimpse of what was to come? Talk about Deja vu.

I got all the feels when I saw him the other day while shopping for chocolate ganache cake and peach yogurt for my kids. I’ll bet you can guess where I was shopping that day. It was the one and only Trader Joe’s, where he works and I’m their most loyal customer.

A smart, handsome guy with a bedazzling smile likes me. And he works at TJs. No way, did that happen exactly like I envisioned? Why yes, it did.

Other than my conscious effort to work on myself in therapy, followed by a dedication to acceptance and letting go, I’ve felt like I was ready for a while now.

No matter what dating app I tried or whatever dates I ventured on, I couldn’t find anyone who aligned with me. That’s because I knew I was looking in the wrong place.

After cleaning out energy via a junk drawer and letting go of old stuff, a portal opened, and a guy I knew walked through.

Once he expressed interest, we were on. We hadn’t had our first date yet, but I felt the potential for something good.

Then the election results hit us both hard. He admitted that his mental health was on the line, and he needed to step back. I graciously supported his endeavors to take care of himself and we parted ways amicably. We shared a couple of tight hugs a couple of days later, but that’s it.

My friend called him a “feisty one,” and said he was a flirt and probably would be great for having fun. But the implication was that he wasn’t available for anything serious. If she’s right, he’s not the man for me after all.

He’s just one Trader Joe’s employee who happens to like me, not my perfect match. I’m looking for a long-term relationship, something he might not offer. Ahh well.

And you know what? I wasn’t crushed. It’s a new feeling for me to not be devastated when someone isn’t ready or doesn’t want the same things.

What changed?

Everything and nothing. I’m still single, I love myself and feel confident I’ll make an excellent partner one day. It was less of a hack and more of a period of intense personal growth that changed me.

I’m not as itchy as I used to be, desperately seeking a scratch from someone else. I use a back scratcher, and I’m good. I’m fiercely independent, anyway, so letting go of finding a person to fill my needs was easier than I thought.

When I stopped acting from a place of codependency, I stopped playing games to get attention. No more attempts at turning fantasies into a reality I conjured. The dating game feels unnatural and chasing people feels disingenuous and humiliating.

As I get older, I not only accept others where they are, I accept myself. My boundaries are clear and consistently maintained. I’m not afraid to say how I feel, which makes it easier to play.

I stopped caring about appearances or age-related changes. My body has birthed two babies and gone through a transformation from substance abuse and generational trauma. I’m a walking miracle, and my signs of aging and healed wounds make me beautiful.

When I was younger, I automatically had my looks to fall back on. Now, I’m shining from the inside out. It’s fascinating how my arms have started to sag, my hands have grown age spots, my tummy has softened, and I feel sexier than ever.

I don’t care if someone doesn’t want to be with me. Of course, I’d like to connect, but I’m not worried if we don’t because I’m not relying on them to complete me.

After two weeks of delightful flirting, I’m alone again. Nothing has changed, and everything has changed.

Like my junk drawer, my insides have been rearranged, making space for another lover or lifetime mate who probably works or shops at Trader Joe’s.

I’ll keep my eyes and heart open and see who I find smiling at me in the grocery aisle.

*Originally published on Medium