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.

She passed over two decades ago, and it has only been recently that I started talking to her. It’s kind of like prayer, but instead of to God I’m talking to her. And ever since I started talking to her, she sends me signs in the form of a rose. It’s usually clever roses, hardly ever an actual rose flower.

And then I started talking to her about men, about how I was in a place where I wanted to meet the love, or a love, of my life. She listened and said she would ask around. See what other grandmas had single grandsons that might be a good fit.

I told my childhood best friend Janet about this, and we giggled as we remembered that we once choreographed a dance to the song Iko Iko, and we adapted the lyrics just for fun:

My grandma and your grandma, sitting by the fire. My grandma says to your grandma: I’m going to set your world on fire!

I imagine my grandma Shirley mingling with other dead grandmas and conspiring to “set my world on fire” with one of their grandsons. A few have come through, each with a sign of a rose. Not an actual bouquet of roses from said man, but that would be romantic. The signs have been subtler than that, as if a little cheeky wink from Grandma Shirley.

So far, the men with the rose signs have been more like bridge boyfriends than something long term. But that’s just sometimes how set-ups go.

So yesterday I was minding my own business, making a last-minute run to a dress shop for a last-minute photo shoot (for this morning). I walked into the shop and there was one other woman shopping. We both ended up heading to the dressing room at the same time so I chatted with her through the dressing room wall as we were trying on our things. Each time I tried on a new dress I exited the dressing room to check it out in the big mirror and I urged her to do the same. She was warm, but reluctant. So we just chatted through the wall instead.

One of the dresses in my dressing room haul was a white dress with red roses. Even though I am not big on patterns, red isn’t my typical color palette, and its midi-length is not my style, it caught my eye because of Grandma Shirley. I was trying it on for her more than anything else. And of the seven or so dresses I tried on, the red roses one was the only one that really stood out.

But now I was the reluctant one. I liked it, but it wasn’t a hell yes. So I set it aside at the register and contemplated it while I did a loop of the perimeter of the store to see if there was anything I had overlooked. As I did that the woman in the dressing room next to me checked out. And as she left out the front door of the shop, the woman who rang her up said: Bye, Shirley. I’ll see you next time!

…to be continued…

There was a lot of initial synchronicity, including the fact that we both had early active Saturday mornings in nearby parts of town. He was refereeing back-to-back soccer games, and I had two beach yoga groups lined up. So it was an easy yes when he invited me to coffee near where I was teaching yoga.

What started as coffee turned into lunch. Once the restaurant closed, we lingered longer in some chairs under the palm trees, and when it got too hot outside, made our way to the crisp air conditioning of the dive bar next door.

It was filled with ease, vibrancy, and connection, and I was glad that, for once, I didn’t have anywhere else to be.

And don’t get me wrong, I have had rich experiences that don’t cost a thing. But if I had my druthers for a first date, I’d be sipping expensive coffee over good conversation with an attractive man in a bougie hotel with an aesthetic lobby.

Which is exactly how I found myself walking up to my favorite hotel, my date waiting for me on the steps to the lobby.

“Did you have any trouble finding parking?” he asked.

“Easy, peasy. I parked on the street. How about you?”

I am not sure if it was any trouble for him or not, but this man did not find a spot on the street. Instead, he valet-parked, to the tune of $50.

I gasped.

Here’s my case for a first date coffee date:

• Coffee will never bum me out, I love it so much. And being absolutely stoked is the frequency I am going for. It helps if your date also likes coffee, but it’s not essential. Like what you like, want what you want: that’s your frequency.

• It is intentionally stingy with your time and energy. Your frequency is expensive, honey; this is how you treat it like an absolute luxury item. And what a wonderful litmus test: if you leave wanting more that’s your clue that you should say yes to a second date.

But back to Mr. Valet.

I gasped because I thought it was wild to valet for a coffee date. But then I realized, he just upgraded my druthers for a first date (adds “who treats my time and energy like it’s expensive and worth it”).

Coordinating anything with Ron is always filled with such ease: loose plans and I’ll see you when you get there. It is intentional, without being over-engineered. And the whole point is connection. On a recent coffee date between friends, we met on the beach to paddleboard to coffee.

Fun-in-the-sun vibrancy and vacation-vibe ease meet intentional connection and coffee-with-a-view luxury.

Yes, we chose a vibey destination and lively conversations, but don’t get it twisted. Our surroundings made it that much easier to get into our frequency, but we were the frequency that day.