Intentional Coffee with an Unintentional Stranger

Chelsea Walker Flagg
5 min readNov 14, 2018

​“Hey, Laura!” I wrote in my email. “Long time no see. Can I take you out for a coffee date soon to catch up?”

Let me stop right there. Anyone who knows me knows that I’m quite possibly the worst ever when it comes to keeping in touch with people. Just ask any of my high school or college friends. What friends, you ask? My point exactly.

What I’m saying is, this email was a big deal. I hadn’t seen Laura in well over a year, and I was trying to turn over a new leaf by reaching out to her.

A respectable 24 hours later, she responded: “Are you sure you’re emailing the right person?”

Ouch. I mean, yeah, I’m a putz at keeping up my relationships, but there’s no need to be snarky about it. Still, Laura was known to be a bit sarcastic, so…

“Yes of course I meant you!” I responded milliseconds later because I never did figure out dating etiquette. I offered up a time and place to meet, and she accepted. Whew. That wasn’t so hard.

The day of our scheduled date, Laura sent me an email. “I’ll be sitting by the front window, wearing a green vest.”

Seriously? It’s not like we haven’t seen each other in a decade or something, I still remember what you look like. Geez, Laura. Your sarcasm is getting a bit out of hand. Will you be holding a red rose, too?

I showed up to the coffee shop and looked to the table by the front window. Sure enough, a woman wearing a green vest (no rose) was sitting there. But, it most certainly was not Laura. Turns out, I’d been emailing back and forth with a COMPLETE STRANGER…

I stared in disbelief at her until she looked up and smiled. I’d been noticed. At that point, I had two viable options:

  1. Run like hell out of that place and never look back
  2. Fake my way through a friendly conversation as though I had indeed emailed the right person

But wait, you ask. Isn’t there another option? Couldn’t you just admit you’d made a mistake? To which I say, are you crazy?! She’d already given me a chance to realize my wrong-doing. No way was I owning up to this.

“Chelsea?” She asked, extending her hand to shake mine. “I’m Laurie.”

YOU GUYS!!! The woman I’d sent multiple emails to didn’t even have the same first name as my actual friend!

“I know that!” I lied, bypassing the handshake and going straight in for a hug. “It’s so great to see you, Laurie!”

Option #2 was now in full play.

Ms. Green-vest already had a drink, so I excused myself to order some tea. Luckily, there was a short line at the register, which meant I had approximately forty-nine seconds to do some serious detective work.

I searched Laurie’s name in my emails and learned that while we’d never actually exchanged personal messages (other than to set up our little date), we were on the same email promo list for a yoga organization I’d done some work with. That’s as far as I got before it was my turn at the counter. Not wanting to be that guy, I begrudgingly put my phone away, sending up a silent prayer that my tiny sliver of discovered information could get me through the next hour of my life.

I made my way back to the table, repeating the name of the organization over and over again in my head as I walked. “So,” I started right in the second I sat down. There was no way I was going to give this conversation a chance to get awkward. “How’s the yoga world treating you?”

“Oh, I left that job last year…” chirp, chirp. So much for not letting things get awkward.

But, I didn’t give in. Nope, not even a little bit. I rolled with the punches and asked her what she was up to now. She told me, but don’t ask me to repeat it because I wasn’t listening to a word. I was far too busy making sure I was nodding at the right times and laughing when it seemed appropriate. I even managed to touch Laurie’s arm a couple of times, just to really assure her that we knew each other. In other words, I was crushing it.

Finally, after 45 non-awkward minutes (I know, right??), I finally drummed up the nerve and said, “You’re probably wondering why I asked you out to coffee since we don’t know each other too well…” (err….at all…)

Her face relaxed, like she’d been holding in that exact question the entire time. “It’s just…” I came up with the fib one precious word at a time. “I…Ever since…we were involved in that organization together…I’ve always looked up to you as…as a strong woman in the area…” That probably would’ve been sufficient enough. But, no, I had to keep going. “and I’ve…made a list of all the strong business women I know…and am asking them out to coffee…one by one…to get inspiration for my own life…”

She was flattered. And rightfully so. My delivery was so realistic, I almost believed my own lie to be true. She asked me if I could please send her that list of strong women. Of course I could, because that’s what friends (err…people pretending to be friends…) do.

We said our goodbyes, and she hugged me like she meant it. Like she finally believed we truly knew each other. It was beautiful. Then I got the hell out of that place and never looked back. Boy, did I learn my lesson. Sorry to all my old acquaintances, but I’m never emailing you again. It’s just too risky to try to catch up with you.

And now, if you’ll excuse me, I’m off to make up a list of influential business women so I can email it to my new BFF Laurie…

Originally published at www.chelseaflagg.com.

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Chelsea Walker Flagg

Personal Growth Coach. Writing Coach. Author. Not afraid to publicly drink pickle juice straight out of the jar