This is part of a series inside the series of my 101 Coffee Dates. It feels overwhelmingly pertinent to mention my Grandma Shirley’s role in all of this, part 1 is here>
I started talking to my Grandma Shirley in meditations. It felt like an easy way to connect with one of the women who had come before me. Whatever thing I was contemplating at the time, I would invite her into my meditation to guide me. When you are talking to yourself in meditation, it is entirely possible that the voice you are hearing is your own, but I’m not entirely sure it matters.
Grandma Shirley always encourages me to go after the thing on my heart, and she is astounded by the opportunities that I have that she never got to know. She urges me to have the time of my life and to suck the sweet marrow out of this one precious life of mine. She reminds me that I live in a wonderful time of opportunity and that I have everything to gain by swinging for the fences.
And she sits with me in my dilemmas as equally as she does in my disappointments. Which is actually where the idea for her Matchmaking Club started.
I met a man for the first time on a coffee date. He wasn’t my typical type, but he was attractive, a great storyteller, and by all accounts, the coffee date was a delight. As we headed to the parking lot at the end of our date, I caught a glimpse of one of his tattoos. I pointed at the one that looked like someone’s name and said “tell me more.”
The tattoo, it turns out, was his grandma’s name. He told me about his sweet relationship with her growing up, how she practically raised him. And when she passed he wanted something to remember her by.
I listened with rapt attention, and when he finished telling me about her, I asked the burning question on my mind: do you talk to her? To which he replied, yes. It felt like permission to tell him about my Grandma Shirley. And that conversation made it one of my favorite coffee dates.
I couldn’t wait to tell my Grandma about it. We squealed with delight at the fun of it all. And then when I never heard from the Man with the Grandma Tattoo again, I was bummed. While I love coffee dates, this is the hard part for me. Letting the comings and goings be easy. Some are easier than others. It’s not quite like a broken heart, how can it be after just an hour with someone. But it’s a little tear in my bubble of hope, if I was being honest. And of course I had to break the news to Grandma Shirley.
This version of her that I talk to, she understands disappointment, but she doesn’t see the point in lingering in it. She urges me to keep going in an onward-and-upward grandmotherly way, but she’ll listen for as many days as I want to talk about it.
And after a few days of talking about the Man with the Grandma Tattoo, an idea started to form. She would ask around to other grandmas. See who had single grandsons that might be a good fit. Perhaps she could find me more where this came from.
And so my Grandma Shirley’s Matchmaking Club started.




So much wisdom in those beautiful quintessential 80s grandmas!