And Now For Something Different...

My Stint as a Smuggler

On New Year’s Eve, my brother Scott gave me a simple task. I was to find out what kind of ring his girlfriend Dana might like. And of course, be cool about it.

I hadn’t seen Dana in a few months and it’d be a few months more till I’d see her again. This was my chance.

I was determined to be smooth and I was. So smooth, in fact, that I didn’t ask Dana a single question about rings, diamonds, settings, weddings, relationships, jewelry, accessories or even circular objects. I didn’t ask her anything. I completely and totally failed, a fact my brother was not shy about expressing.

Either as chance for redemption or plain punishment, I was sent hundreds of pictures of rings. Over and over, the question was, Would Dana like this? It’s always safer to say no than yes and I said no a lot, continuing my role as Unhelpful Sister Number 1.

Finally, my brother gave me a task that played to my true strengths: cunning spirit, deft hands and ability to omit the truth with reckless abandon.

Like that, I became a smuggler.

With painstaking attention to detail, Scott designed a ring for Dana and—to avoid Cook County taxes—had it shipped to my little office in the city of brotherly love. My mission was to tell no one, not open the box, not let it leave my sight, smuggle it across the country in a carry-on bag the following day and deliver my brother’s most expensive (and carefully plotted) purchase safely to him.

The day the package was supposed to arrive, I was in an all-day brainstorm session on the other side of the office. I left a note on my desk saying where I was, so that whoever signed for the package would know to bring it to me. My brother had been adamant about me not letting it out of my sight.

I knew there’d been a misunderstanding when I got this email.

Package Secured (Sort of)

The ring was safe, so I wisely chose to not tell my brother about the email until right now.

I borrowed a second duffle bag from my roommate, packed what is clearly a gigantic package for an engagement ring and flew to Chicago. An overweight man with a deviated septum slept next to me on the plane, and at times on me, as I protected the ring-in-a-box-in-a-bag tightly between my feet.

I delivered it to Scott the next day in a public space with a lot of noise. That wasn’t part of the plan, but it felt right. We waited another a day to open the box and admire the ring.

My brother did an amazing job.

Where I met my brother for the

Where I met my brother for the “drop off.” I’m shielding the package from the camera, as the consummate professional does.

Nice Manicure Dana

The ring, ladies and gentleman.

Fast-forward to today. Scott and Dana are engaged. Our parents are thrilled. And the CIA has already contacted me about utilizing my stealth services in the near future.


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