top of page

Trying Not to Be ‘That Guy’ at the Dinner Party

How Do We Talk About Our Around-the-World Trip Without Sounding Like Insufferable Jerks?

Ah the rolling hills of Tuscany. It was a crisp, clear day and we toured this delightful winery with ... oh just shut up already Jim.

I looked down at the bottle and recognized the name. “Is this the winery we visited in Italy?” The bottle we’d picked up at the market would serve as a gift to our friends, as we headed to the dinner party in their home on U Street.

“Yup. Antinori,” my wife confirmed. “And the Antinori winery owned the vines around the villa where we stayed. Remember those hills? That view?”

My mind rolled back to Tuscany, where we’d spent five amazing days just five months ago as part of what we called our one-year retirement. Megan’s mother had always wanted to learn about Italian cooking from a master chef, so she joined us for Italy, where she had booked a Tuscany wine and cooking experience. Our standard of living on the trip went up significantly on that leg, with specialized one-on-one cooking classes and chauffeured winery tours. It included a special lunch at the famed Antinori winery, which overlooks the family’s vines from a hillside. The massive winery itself is built into the hill, with a state-of-the-art touring facilities and beautiful architecture. “This is like the disneyland of wineries,” I told my wife at the time.

“That’s a great story to go along with the bottle tonight,” I said. “But we shouldn’t tell it. We’ll sound like jerks.”

One of the best parts of being back in Washington, D.C. is reconnecting with our friends over dinner or drinks. We get to catch up on their lives, and they hear about our travels. Every time, people keep saying, “You’re probably tired of people asking you questions. I’ll stop.”

Please don’t. We love talking about the trip. It was a big decision for us, and one we’re very happy we made. Plus, it helps us with memory retention, as there were so many locations and experiences that our biggest problem now (besides the minor concern of finding jobs and an apartment) is keeping everything straight in our heads.

But one real worry I’ve had would be that we’d start to sound like insufferable jerks. Just the sheer scale of what we’ve seen and done becomes overwhelming when I think about it. Imagine going on the trip of a lifetime, spending two weeks exploring those international destinations you'd always wanted to experience. Then do that again 25 more times. That’s what we did, and that’s exactly how it felt to us.

In the same journey, we went cage-diving with great white sharks, we hiked to Machu Picchu at dawn, we took in the Paris skyline from the Eiffel Tower and swam with sea turtles in the Galapagos. We’ve walked some of the world’s greatest cities: Tokyo, Berlin, Sydney, Buenos Aires, London. We’ve gazed upon the fantastic wonders of the world: The Sistine Chapel in Italy. Ankor Wat in Cambodia, Ha Long Bay in Vietnam and a Maasai Mara safari in Kenya. When I think about all we've done, it doesn't really seem real, and it certainly seems too extravagant to talk about with our friends. Even just writing this paragraph makes me want to punch myself.

We realize we are extremely lucky to have been in the position to take this trip of a lifetime. When the opportunity arose, I had saved my money for 30 years and so had the resources that would have otherwise gone toward a house down payment. We didn’t have children or other responsibilities to tie us down. And we knew we’d travel well together because we both had similar traveling styles. But my concern is that our appreciation for the luck we’ve had in life, and the luck we’ve made for ourselves, doesn’t always come across in polite conversation.

As we walked to our friends’ house, I imagined our upcoming conversation in their living room that night, with my words sounding as if they were dripping with condescension: “Here’s a bottle of Antinori. We toured this winery when we were staying at a deee-light-ful villa in Tuscany. Just a magical place. You really must go there if you have the chance.” In my mind I was suddenly transformed to a character I’ll call Snooty McUpperCrust, donning a top-hat and monocle. Perhaps I’d throw back my velvet cape as I spoke, to provide an additional flourish to my insufferable words.

Of course I’m probably more sensitive to the words I use because I’ve spent a lifetime in the public relations industry, where every syllable matters and every effort is taken to ensure there are no unintended messages. So perhaps I should stretch my PR muscles a bit and give myself a debrief on how best to “message” the trip with my friends. Here are my talking points for "messaging" my One-year Retirement:

  • Rule #1: No Unsolicited Comparisons: Unless someone asks, don’t volunteer comparing something you’re experiencing with something you experienced on your One-year Retirement. There are plenty of bests on our trip that we could list as our favorites — best value tourist destinations, friendliest people, best place for sunsets, best hotels and Airbnbs — but unless the conversationalists have been there or intend to go there in the near future, they don’t need to hear about how what they’re currently experiencing isn’t the best in the world. This is especially true for food. We experienced an amazing array of fantastic meals on our trip, and we’d be sure to try the local dishes a city or country was known for: pho in Vietnam, pasta in Italy, croissants in Paris. There’s a reason these places are known for these foods; it’s because they’re very, very good at what they do. But blurting out,“I love this Vapiano, but nothing beats the Cacio e pepe we had in Rome,” ain’t gonna win over any friends. If someone asks me what I thought of the ramen in Japan, I’ll tell them. Otherwise I’m keeping this to myself.

  • Rule #2 Don’t Complain About Traveling Life: There are some elements of long-term travel that are challenging and frustrating, to be sure. The lack of a routine, the challenges staying connected with friends and family, and the constant need to maintain your travel planning for the rest of the trip were all more difficult than we expected. And because everything you do — ordering food, finding your hotel, understanding the cultural norms — is just slightly more difficult in another country, all those little frustrations can really add up and become exhausting over time. But for me, it was still better than real life. Even if your waiter gave you the opposite of what you ordered, you were still in a cafe in Hanoi instead of working at your desk back home. Nobody wants to hear about how hard it was to be on One-year Retirement. It wasn’t hard, it was a little challenging. Real life is hard.

  • Rule #3 Don’t Talk About Being Busy and Retired: OK, those of you in the real world who are retirees, I understand it now. You really are busy. My retired mother would talk about how busy she was but I didn’t understand how a day could go by so quickly when you didn’t have a job occupying your working hours. You have at least eight hours of additional time for yourself each day. How can the time fly? Well it does. I feared I’d be bored at points on our trip, but instead there were points where I was the opposite — overwhelmed and exhausted. But the non-retirees I spend my days with now just don’t get it. And they probably won’t, until they’re retired someday and wondering themselves where all the time went. So for now, I’ll parse my words, and only talk about this with my real-world retired friends and family.

As time goes on, the questions from friends and family will fizzle out, as real life settles in. People will stop asking about our favorite place or the best food or if there were points in the trip where we felt unsafe. Until then I’ll be looking forward to re-energizing our memories of the trip by talking them through with my friends and family. I’ll be watching my words, and I’ll recount how we enjoyed the lovely scenery in Tuscany — but only if they ask about the wine.

You Might Also Like:
bottom of page