My 70-year-old Grandma And I Started Dating At The Same Time. It Brought Us Closer Together.

The author was 23 and their grandma 70 when they both started dating new people.

Courtesy of the author

• My grandpa died in 2020 and I visited my grandma regularly to offer support. 
• I learned a lot about her, and never expected for us to start dating at the same time. 
• She asked me for dating advice and sent me outfit checks before dates. 

I never expected my grandma to ask me for dating advice, but when we found love at the same time, within a week of each other, we were so excited to experience it together.

In May 2020, my grandpa died. I watched my grandpa's funeral service from behind an iPad screen outside the funeral home with limited occupancy at the time, my younger cousins dancing under the carport. I held my grandma's arm as we walked through the cemetery, and we ate pizza at her house afterward.

Taking one day at a time, I had no idea how to move forward and how to support her besides being present and keeping her company in the silence. We started scheduling regular visits; I would go down and stay the weekend with her, help her organize the mail, drop off packages, pick up groceries, and more household tasks she needed my assistance with.

Our bond really deepened

I learned so much about my grandma, and our bond as her oldest grandkid deepened. We shared inside jokes about Grandpa's burial experience, watched Hallmark movies, and went through the Culver's drive-thru daily.

Our inside jokes went hand in hand with secrets we would share. I talked with Grandma about dating, being on dating apps, and the struggles of trying to meet people during the pandemic.

I explained how draining it was to identify people with red flags, get past the talking stage, and she shared her concerns about trying to find someone at a similar life stage as her. It was difficult to imagine her opening up her life to someone new, and I think we were both pleasantly surprised when it did happen.

We started dating at the same time

That summer, between visits to my grandma, I met someone in Milwaukee, about 114 miles away from my apartment, and things steadily grew from first dates to weekly phone calls and beyond. I shared lots of updates with Grandma as we progressed from Tinder notifications to texts and pictures and voice memos. That someone I was seeing soon became my girlfriend and someone I loved, and my grandma was ecstatic for me.

At the same time as me, my grandma had started seeing someone. Our dating anniversaries are within a week of each other, and many of our relationships' firsts overlapped.

My grandma is a private, loving person, and this new relationship quickly blossomed from group luncheons with fellow high school alumni to solo outings at the local botanical gardens and city diners.

I knew she had reached dating territory when Grandma complained about the youthfulness of the term "boyfriend," which did not feel adequate to capture their shared lived experiences, even though it made her smile to have him referred to as such. We settled on beau as his romantic label, and I became her "official dating coach."

Grandma's new beau had also lost a spouse to cancer, and she frequently told me about how important that shared lived experience was to her. Watching from the sidelines, she took to dating much more easily than many baby boomers might in her situation. My grandma is good at asking questions, giving information, and she spent lots of time analyzing her new beau's answers.

She would send me outfit checks before dates

Grandma would send me outfit checks before a date, asking about the level of dressiness depending on the venue. Her favorite color is Wisconsin Badger red, often donning a blazer or turtleneck sweater for the cooler months. My girlfriend and I would offer tips about layering, accessorizing, and makeup tips. These 'fit checks would usually come early Friday mornings since she had a recurring appointment every Friday for lunch with her new beau.

Those regular plans became a highlight of her week and our weekend debrief when I came to visit, we would giggle and share pictures and recount the events over ice cream sundaes late into the night.

This information was confidential for a while, kept private from the rest of the family while the relationship developed and Grandma ascertained her feelings. They went public over Thanksgiving, with a phone call to each family member, breaking the news. She ended her call to me with, "do you have any questions?" and my girlfriend and I laughed since we were together. We did not have any questions because we had been along with the ride from the start, and six months later our own relationship had progressed beautifully. I was spending the night, walking her dog and sending grandma pictures from our own outings.

A year and a half later, Grandma's beau became her husband. He is a kind man with his own kids and grandkids, someone who absolutely adores my grandma. He worked diligently to gain trust and acceptance into our family and honors my grandpa's living memory with his love and care for our family as well.

Marriage looks good on them, as they giggle together, make inside jokes, and chat about decorating the house and planning for their future trips to visit out-of-state children and grandkids. The honeymoon phase after a decadeslong marriage is filled with just as much joy, love, and excitement as I have ever seen.

Seeing my grandma find love for a second time reaffirms my belief that everyone has the chance to find multiple great loves in their lives, because she found hers.