“When in Rome!”

“When in Rome!” is a shared refrain that Alex Nilsen and Poppy Wright use to make spending feel like part of the trip rather than a departure from their usual habits. First prompted by an extra drink during wine tasting, it becomes a lighthearted permission slip for indulgence; in Poppy’s account, that growing ease with spending sits alongside a more difficult question about what travel can—and cannot—provide.

Origin and Meaning

The phrase enters their routine on the second day of wine tasting, when Alex orders another drink and cries, “When in Rome!” The appeal is less a literal invocation of local custom than a joking rationale for enjoying what is at hand. Afterward, when either of them hesitates over a purchase, the other invokes the same words. Repetition turns a single impulsive decision into a private ritual: spending becomes something they authorize together.

A Shared Permission to Indulge

At first, the ritual covers enormous ice cream cones, used paperback books, and plenty of wine. It grows into a decision to eat at Farallon, a costly San Francisco restaurant. They are hungry and do not want to work through Poppy’s compiled list of options; the restaurant’s expense is acknowledged rather than ignored. Its opulent rounded ceilings, gilded fixtures, and golden-edged booths make the meal feel like a fitting place to spend too much. Poppy declares, “No regrets,” and makes Alex high-five her. His murmured objection that high fives make his insides feel as if they have poison ivy preserves the couple’s teasing tone even as they affirm the choice together.

The refrain therefore gives their purchases a social shape. One person’s hesitation is met by the other’s encouragement, and the pair can treat a costly meal or an extra drink as part of a shared adventure. Its humor rests on the contrast between the grand-sounding justification and the modest items it often licenses, from a paperback to an ice cream cone.

Travel, Display, and Limits

The phrase also resonates with the tension between Poppy’s budget-travel roots and the more polished travel image associated with her work at R+R. She usually writes about how to travel on a budget and make the most of the least, while her large audience makes a conventional beach vacation seem like the expected subject of a post. On Sanibel Island, however, she and Alex spend only about forty minutes on the shore during a week, passing much of the rest of their time in bars, restaurants, bookstores, vintage shops, and the shabby bungalow, where they eat popcorn and watch a Twilight Zone marathon through the storms. The trip’s reality does not match the easy, sunlit vacation their audience might expect.

That gap recurs in Poppy’s account of work travel. She recalls that the trips changed after she got the R+R job: instead of the chance encounters that had made her feel connected, she met chefs and hotel managers seeking write-ups, and returned from impressive trips feeling empty. Even a proposed summer trip to Palm Springs raises the conflict between her preference for a cheaper, less crowded visit and the magazine’s aspirational brand. Later, she anticipates combining a work trip with the annual journey with Alex, imagining their ratty T.J. Maxx luggage arriving at a resort where they will be greeted with champagne. Against those polished images, “When in Rome!” marks a more immediate pleasure: the two friends’ willingness to enjoy what is in front of them. The refrain can make an indulgence easier to choose, but it does not make travel itself a guarantee of happiness or connection.