Uncomfortable February Highlights: Week 1
This month, I’m doing a daily challenge to get out of my comfort zone. Here are a few highlights from the first week.
Buy a coffee for the person behind me in line at Starbucks
The line was long. I got in, anxious to see who would end up behind me. I hoped it would be someone I knew from the office. Or at the very least, someone who looked familiar. An acquaintance. That would make this experiment more tolerable. More appropriate.
A few seconds later, a guy around my age stepped behind me. He had a large beard and a messy head of hair — like he could have worked at Patagonia. Clearly, he did not work in my office building. Fan-fucking-tastic, I thought. He pulled out his phone and proceeded to scroll.
I decided this wasn’t the guy for me. I’d come back and do it later.
NO! That’s not how this works, I told myself. Push through the discomfort, dammit. That’s what this whole experiment is about.
I rehearsed the scene in my mind at least eight times. I went through every possible scenario. What if he’s ordering food? What if he’s doing a coffee run for his colleagues and needs three trays of drinks? I’m definitely not paying for that, I told myself. One drink, that’s the deal. No breakfast sandwiches or shitty croissants or morning buns.
I opened up the Starbucks app and cued up the payment screen, wanting to get this over with as quickly as possible. My heart was racing. Dry mouth. This should not be this difficult, I told myself. It’s one drink; a nice gesture.
The barista looked at me. “What can I get started for you?”
“A tall blonde roast, this yogurt, and…”
I turned to the guy behind me, “Are you getting a drink?”
He looked up from his phone. “Yeah,” he said, a little startled.
“It’s on me,” I gestured to the barista.
His face lit up, “oh!” He didn’t even try asking “are you sure?” to give me an out. The woman behind him in line watched the entire interaction and smiled.
I said something like “Happy Friday” or “yeah, pay it forward!” — I don’t remember. He looked at the menu and ordered a “regular” cinnamon shortbread latte. He patted me hard on the shoulder, the way a close friend would. “Thanks, man.”
I paid. I felt ecstatic. The execution felt clunky. And I didn’t care.
Pushing through the initial discomfort was worthwhile. That discomfort came out of insecurity and fear of the unknown. Would it look weird? What if he refused? What if he was in fact ordering 16 drinks?
Of course, a nice gesture like this is not weird. It’s kind.
It felt good to do something nice for a stranger.
Buy a bra at Victoria’s Secret. Return it several days later.
I have never been inside a lingerie shop, let alone a Victoria’s Secret. Nor have I ever purchased a bra. So when my friend Sam recommended this challenge, I knew I had to do it.
I took my time meandering through the Glendale Galleria without consulting the map. It felt more organic to simply stumble upon the bright pink fluorescent storefront. Eventually, I found it, on the opposite side of the mall. I snapped a photo from afar and texted it to Sam with the message “This is about to happen.” Now I was on the hook.
I strolled in, attempting a swagger of confidence. After I crossed the threshold of the white-floored mall onto the dark-black tile of the store, I made it three steps inside before I was nearly knocked over by a sales associate.
“Hi there! What can I help you with today?” Despite my fake confidence, I read this as “Hi there little boy, are you lost? Do you need your mommy?”
I quickly made up a story about buying a bra for my girlfriend and answered a series of questions I was not prepared for. Lingerie or basic? Size? Color? Pushup? “I have just the one,” she said, “and it’s on sale too!”
Score! I do love a discount. Even on items I have no intention of keeping.
Throughout the entire exchange I felt as if I was observing it from afar, like I was not in my body. I was awkward and anxious.
She handed me the bra and pointed me in the direction of the register. She didn’t ask if I needed help finding anything else. She must have sensed I wanted to get out of there ASAP.
“Thanks sweetie. My name’s Martha.”
The entire shopping experience took less than two minutes. The checkout line took about fifteen. My feelings morphed from self-consciousness (is there a right way to hold a bra in a check out line?) to humor (of course this is taking forever) to frustration (come on!). One associate helped a woman with a large, complicated exchange, while another tried to calm a frustrated customer who wanted an exception made to their return policy. I commiserated with the person behind me about the length of the wait.
I noticed there were two other men in line behind me, both with their partners. It felt good to have company.
Finally the transaction happened. I walked out, feeling good and jittery and relieved. I had done it.
Well, half of it. I want my $32.30 back.
Talk to a woman I find attractive
Talking to strangers is something I keep wanting to become better at. But I keep putting it off and making excuses. Several friends and family members contributed ideas to my Challenge List related to talking to strangers or asking women out. These challenges are not about box-checking — the idea is to engage in these challenges when the moment is right, anytime throughout the month.
One night, I had spare time before a dinner so I decided to peruse the shelves of one of my favorite bookstores, Skylight Books in Los Feliz.
After a few minutes looking through the western philosophy section, someone walked inside who took my attention away.
She was a curly, red-haired woman wearing a Patagonia fleece pullover — the same type of pullover I had been looking at online earlier that day. Funny.
She had freckles and bright blue eyes and was probably a few years younger than me. She spotted me looking at her and smiled. I smiled back. This is the moment, Jared, I said to myself. You need to try talking to her!
I didn’t.
My mind raced. What do I say? How do I approach her in a way that’s “normal?” I stood there, pretending to look at Marcus Aurelius’ “Meditations,” wondering how to break the ice. Maybe I comment on her on her fleece, that could be a good in.
Then, her friend entered the store, and the opportunity was lost. Approaching a stranger is hard enough. But a stranger with a friend? No way.
I continued to walk around the store, spotting the psychology section in the back. As I approached the shelf, I noticed her flying solo again, looking at the sale section hidden in the corner.
I stood there, tension filling my chest. Say something. Anything. If she doesn’t want to talk to you, you’ll know. At least you can say you tried. A line came to mind — one that seemed harmless:
“So this is where they hide the sale section.”
She turned and looked and me and smiled.
We talked for about 15 minutes before she had to leave. I was a giddy, nervous mess, like a pre-pubescent teenage boy talking to a girl for the first time. I sensed that she felt similarly, too. It felt nice to be on the same page with someone, experiencing a mix of nervousness and excitement. We talked about books and art and our jobs.
I got her name but not her number. A missed opportunity — maybe. She was visiting from northern CA. It felt best to enjoy the moment for what it was and not have further expectations from it.
She left the bookstore with her friend after paying for a puzzle. As they walked past the storefront outside, she turned at the last possible moment and looked inside at me. I smiled.
These interactions will not always go this well. Though it’s nice to know that they can. Even if I feel like an awkward mess on the inside, it felt good to connect with someone else.
