Dating at a Thrift Shop

“Hey, cool pin!” I noted as I sat down on a rickety wooden picnic table bench across from my date. He was wearing a round pin with the iconic image of Rosie the Riveter on the left pocket of his jean jacket.

“Thanks, it’s my favorite,” he replied with a genuine smile. He greeted my dog Anchovy with affectionate scratches while simultaneously wiping the frothed milk from his upper lip. This was the first time I brought Ancho with me to a first date, and I figured it would be a good way to immediately vet the guy. If Ancho was uncomfortable with him, it’s probably not a great sign.

We decided to meet at Stanza Coffee, a cafe in the heart of the Mission District. Next, the plan was to venture to Mission Thrift after fully caffeinating ourselves. This would be no ordinary shopping trip — we each would choose an outfit for the other that we would wear for the rest of the date. The more ridiculous and outrageous, the better.

“You know, I don’t get embarrassed easily,” he warned with a look of challenge in his eyes.

“Joke’s on you,” I retorted. “I’m never embarrassed. May the most shameless person win.”

For obvious reasons, let’s call my date Macklemore. After we finished sipping our coffee, Macklemore, Anchovy, and I headed to Mission Thrift, where we found rows upon rows of modern and vintage clothing hung up in disarray. It was the kind of mess that’s pleasing to the eye; it opened up my mind to creativity. I find that clean lines and perfect placement can sometimes stifle my free-flowing thoughts. This was the perfect setting for our game.

“Alright, how should we do this?” I inquired. “Want to find each other once we’ve gathered the perfect outfits? I’ll start on the right side.”

He agreed, and we split up in opposite directions. I had the obvious advantage with Anchovy being able to sniff out the best costumes in the second-hand store, so I realize that it was an unfair fight. After sifting through a few racks of gently-used blazers, button downs, and t-shirts, I found the perfect one-piece costume: bright yellow rubber overalls. I was done. No further rummaging would get me anything better than I had already found, so I turned to the women’s section for some actual shopping.

After about 45 minutes, Macklemore had found his apparel for me to wear, and we met in the middle of the store for the big reveal.

“I got three different items for you to choose from,” he mentioned as he took the clothing from behind his back to show me officially. He had found a t-shirt with a man’s face covering the front — supposedly some celebrity that I’ve never seen. The next was a loud blazer with a crazy pattern in light blue and black. The third option was a long, elaborate gown coupled with an orange scarf that really spoke to me, so I was quick to choose that one.

“Great. I actually wanted this blazer for myself,” he said. I held the gown and returned the t-shirt to the rack as he tried on the blazer. “It fits perfectly!” I agreed that he should purchase it for himself.

“Let’s hit up a nearby taqueria and grab some food,” I suggested. “You hold the table while I change into this fabulous dress, and then I’ll reserve it so you can grace the world with your new yellow overalls.”

After we paid for the items, we set out for the taqueria a few blocks down. We grabbed our food and took turns transforming our image with our new outfits. We laughed as we had our mini fashion show. The beautiful thing about San Francisco is that we barely got any stares or dirty looks from anyone walking down the street; we fit right in with the other wonderful weirdos that live here.

Wins: This was what I call a ‘double-duty date,’ which is the term I use to refer to a date that can be leveraged for other purposes other than just a few hours of romantic pursuit. Here is a list of double-duty dates you can try yourself:

  • Hiking doubles as a workout
  • Cooking doubles as meal prep
  • Crafting doubles as gift-making
  • Museum dates double as education
  • Dancing doubles as cardio
  • Road trips double as travel/cultural experiences
  • Antiquing doubles as decorating
  • Bookstore dates double as shopping

Learnings: Bring hand sanitizer to a thrift store date. My hands were covered in grime by the time I left to go home with my haul. But it was 99 cents!

Originally published at on October 16, 2018.

An intuitive storyteller with a vision to reduce shame through blunt essays on mental illness. I’m a survivor of Bipolar, Complex PTSD, OCD, and GAD.

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