I walked at a leisurely pace down Polk Street past cafes, Thai restaurants, and gift shops. It was a beautiful morning and the bright sun provided warmth in the otherwise cold temperatures of San Francisco in late fall. When I reached the corner of Polk and Green, I stopped to wave as Allee (today’s diner date) strode over.
Together, we walked the rest of the way to our chosen diner: Chestnut Diner.
The walk gave us a chance to work up a bit of an appetite. It also gave me the chance to give Allee a heads-up about some intel I’d gathered ahead of time.
At a Christmas party earlier in the season, the topic of these diner dates had come up, and a friend mentioned that he'd been to our chosen diner, Chestnut Diner, before. The food was good, he'd said, but the wait times had been really long.
After Allee confirmed that she had no urgent plans following our diner date, we continued on toward Van Ness Street, ready to enjoy our breakfast and to experience this retro diner in the heart of San Francisco.
Chestnut Diner on Van Ness
Chestnut Diner is located on Chestnut Street and Van Ness. Its appearance was exactly what we wanted from a San Francisco diner.
A blue sign featured the diner’s name in bold lettering with the classic checkerboard print at the bottom giving it that perfectly retro feel.
The interiors were just as charming. At the center of the cafe was a curved counter encircled by blue barstools, constructed with that iconic chrome detailing.
On either side of this central counter was booth seating. The booths had pleated vinyl cushioning imbuing the space with that perfect vintage-style aesthetic. The bold tile floors were black-and-white checkerboard to match the sign and the menus. There was also a little wooden table in the window which was unoccupied.
Allee and I stood in the doorway for a moment, unsure if we should wait for someone to seat us. After a minute or two, we noticed an older man seated at the central, U-shaped counter, motioning for us to sit at the table in the window.
He looked like a regular, so we trusted him and took a seat.
We were seated for quite a while without anyone noticing us. Luckily, we had a lot to catch up on and chatted about work, workouts, our new apartments, dating, and life in the city. After a while, however, we began to feel anxious that we shouldn’t have seated ourselves. Maybe no one had realized we were there.
Allee got up and took a seat next to our old man friend at the counter so that she could flag down one of the servers to ask if it was okay that we'd seated ourselves in the window. However, right at that moment, the owner came over to our little table to set down menus.
The menus were a perfect extra-large diner size, rectangular, and featuring that same diner checkerboard pattern on the front. Opening them like books, we perused our options and debated about lunch items or breakfast items.
Allee decided on eggs, potatoes (she chose a crispy hash brown), and toast. I ended up ordering the vegetarian sandwich. We also got a side of social pancakes (because how could we not?).
It was another ten minutes before the owner returned, and we placed our orders (plus two coffees), then relaxed, and fell back into conversation. I felt lucky that we had enough to catch up on, and figured the long wait time was perfect time for asking my usual diner date questions.
Twenty minutes later, our food arrived, and we were thrilled.
Allee’s breakfast was delicious, our coffee was hot, and my sandwich was exactly what I wanted. Vegetarian sandwiches can seem (and often are) fairly simple. However, there are good veggie sandwiches and there are mediocre veggie sandwiches. This one was delicious. It was stuffed with everything: avocado, greens, pickles, cucumbers, a delicious spread, tomatoes, and pepperoncini and served on a toasted buttery sourdough.
I was a big fan of the food at Chestnut Diner and we were both satisified diner girlies.
We had no idea that chaos was about to erupt.
Chaos erupted at the Chestnut Diner
You never know what will happen when you head to a diner, and though this next portion of the recap has nothing to do with the diner itself, it certainly made the experience unique. You can skip down to the hot takes and hot cakes section if you want to read Allee's diner preferences and get the Chestnut Diner rating.
Or...
A few bites into our food, we saw a group of about five runners jogged up outside. At first, there were only three of them. They looked young, and I wondered if they were on a high school track team with weekend practice or a first-year college track team.
After stretching their quads and hamstrings, they came inside and took seats in a booth to our left.
Then, another boy arrived outside. He’d ridden over on his bike and stood looking lost outside. It was obvious that he knew the runners who'd come inside when be started motioning to them. Soon, it became clear that he'd ridden his bike over to the diner without a lock.
As someone who lives in San Francisco (and owns a bike), this is a cardinal sin! This was not a good sign... it is safe to assume that anyone who rode a bike in San Francisco without a lock would not have much common sense. This assumption turned out to be true, and the boy tried to walk his bike into the diner.
The Chestnut Diner is not a large space. It is, as you would expect, a cozy neighborhood diner with very small walkways between seating. As soon as his bike was through the front door, the owner shooed him back outside, shaking her head at the ridiculousness of his attempt.
He stood out on the sidewalk looking dumbfounded. A couple more friends arrived, jogging up, just as sweaty as the others. They proceeded to climb onto each other's shoulders so that they could throw his bike over a bus stop pole to keep it safe. This seemed a good enough solution and the three walked inside to join their friends at the table.
Then, what appeared to be the entire school track team arrived, and the group of 20+ boys tried to pile into the tiny diner.
They seemed stunned when they couldn’t find a seat, and even more stunned when the owner, overwhelmed by them bursting through the door, shooed them out and told them she did not have room for them.
“The Asian lady told us we can’t come in,” I overheard one say to another.
You mean the owner? Correct. There is not enough room for an entire track team to fit into this already filled diner.
The chaos of 20+ young boys all trying to cram themselves into the space and then looking like lost dogs as they milled back outside was quite a distraction, and it took a while for Allee and I to get back to our diner topics. Once they had left, however, we were able to diner dish.
Hot Takes and Hot Cakes
First, what were Allee’s overall thoughts on diners?
She hasn’t explored them as much in San Francisco, but definitely went to a few 24-hour diners in New York City when she was younger. One memory, in particular, makes her laugh, having breakfast at four in the morning with large glasses of wine. There's nothing like a messy morning breakfast to really capture that devil-may-care essence of youth.
Go-To Diner Meal
She loves a classic two-egg, sausage, and potato breakfast. Her preference is chicken apple sausage and she prefers hash browns over home fries. You can’t find them everywhere, but she loves a crispy hash brown that's been flattened on a griddle.
Coffee Order
At a diner, she goes for the classic drip and drinks it black.
“It would be insane to ask for almond or oat milk.”
Counter or Booth Seating?
She’s a counter girlie for sure. Give her a counter or a bar at any restaurant.
“Because you’re up in the action and can chit-chat with everyone.”
Overall Rating for Chestnut Diner: 8.3/10
Atmosphere: 10/10
Food: 9/10
Coffee: 8/10
Staff: 8/10
Detractor points: -1.5 (very long wait time)
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