Natalie Ladd, left, and her BFF enjoy igloo dining last weekend at Boone's in Portland.
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This is not a news flash, but some of Portland’s best servers have had it. 

Hanging on by one insufficient tip at a time, lowball gratuities aren’t the major issue. Instead, it’s a misdirected attitude and something akin to open resentment. 

“It’s the freaking sense of entitlement a hundred times worse than I’ve ever seen,” said a bartender/server who pleaded not to be identified. “It’s worse than not wanting to wear a mask. It’s like they’re doing me a favor simply by being there. Truthfully, I guess that’s true no matter what, but usually, it’s mutual. This situation we’re in isn’t going away and for the first time in years, I flipped out over how people are acting.”

This meltdown from a fellow restaurant veteran further opened my eyes. Typically so positive, it was enough to make me look for a hazmat suit to summon the rationalization to sit at her bar. 

Like many, I’ve resisted dining indoors. The last time I even sat under a semi-enclosed tent, I acted like an amateur and was hungover for two days. That and learning that the place shut down 24 hours later due to a COVID-19 case in the kitchen scared me on many levels. 

Instead, BFF and I have taken to happy hours outside. We plan them strategically when the sun will be shining brightest on the parking spot in front of my tiny condo. Referring to it as “tailgating,” my neighbors have grown used to seeing us in full winter gear with a small table holding cheese, wine, and fancy cocktail napkins. It’s an odd sight, but we’re trying to maintain normalcy in these anything-but times. 

After the chat with my bartender friend, I started looking in earnest at the work so many bars and restaurants have done to comply with safety regulations, and beyond. The massive amounts of money and effort put into ingenious outdoor configurations felt hopeful to me. Once again, not a news flash, but you can’t fully comprehend the scope of the accommodating renovation projects if you don’t venture out and see them up close and personal.

I also began to understand the new layer of frustration our hospitality folks are experiencing. There’s an element of survivors’ guilt in acknowledging they have jobs and others don’t. There’s also the extra work, for less money, involved in opening and closing a dining room with a skeleton crew. Servers are also in fear for their own health and the health of those they love.

On the flip side, because people like me are rightfully scared to go out, we may have an unconscious desire to be applauded for taking risks. Or, more likely, we don’t want to tell anyone we went out for fear of judgment, or of dying. 

In other words, no matter how hard dining establishments try or how much money they spend, those of us who are paying attention are obviously still hesitant and worried. We’re on the edge, and our servers can sense it. However, if we aren’t paying attention to the world around us, we might be diners with mask resistance, and that’s it’s own set of problems. Unbearable entitlement is just one symptom. 

With all this in mind. I’m confident it was the discovery of $1.25 oysters that finally broke us down, but BFF and I found ourselves sitting in a new igloo upstairs on the deck at Boone’s, where our first happy hour off the pavement was both an amazing deal and surprisingly elegant. It was still being set up for photos: There was a sparkly grey rug beneath the table for 6-8 people, a yellow-and-white checked tablecloth and napkins, artificial flowers, and stunning glassware. Hillary, the front-of-house manager, told us we must come back when the twinkle lights go up.

We were lucky and even when those props are gone, that heated igloo will feel compliant, comfortable, and safe. Hillary waited on us and in passing, I asked her how people were behaving. 

“Funny, I was just talking to the bartender about this,” she said. “People are really being, um, I don’t know …”

Jumping in to save her from trashing customers, I asked, “Entitled?”

Hillary looked at me and said, “Yes. So entitled. And we are trying hard. We wear our masks, distance as much as we can. And, we’re shrink-wrapping the deck downstairs and have another igloo. Please come back.” 

We’ll go back, but I’m not sure when. If you happen to go, say hello to the bartender, to Hillary, and smile wide with your eyes. Appreciation speaks louder than entitlement anytime. 

Natalie Ladd is a Portland restaurant veteran, freelance writer, and connoisseur of all things Bruce Springsteen. She loves Boston sports, chewy red wine and has never sampled a cheese she didn’t like. She can be reached at [email protected].

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