Working Class Man Visits High Class Society, What Happens Next Is Shocking

It was the best of times. It was the worst of times.

As a blue-collar working class guy, I rarely have opportunities to travel. That’s why I jumped at the chance to travel to Maine for my good friend’s wedding.

It was more or less an opportunity for a reunion of very old friends and connections, but instead of doing it at a D.C. bar, we'd be doing it in a picture perfect Maine location.

The event was such a high class event that I bought a tuxedo for it. A black tie wedding might as well be traveling to the moon for a person from where I come from, but I was excited nonetheless.

Good people, good times and an open bar is hard to beat. Little did I know the doom that was waiting.

A look at some scenery in Maine. (Credit: David Hookstead)

How does little old David Hookstead fit in among high society in Maine?

Now, I want to be clear that this isn’t the first time I’ve been to Maine. I went to Maine back in 2017 for a trip that in hindsight is almost hilarious to me.

I stayed at buddy's island place with a small group of friends, and looking back seven years later, it feels like we’re in a different world. At the very least, we’re all in different places in life. Many are married with kids, some have become insanely rich, others have kind of faded from the public spotlight while a few from the trip surged forward.

It was an incredible time, and I immediately fell in love with Maine. Seven years later and the stunning beauty of the state, once again, took my breath away.

I was captivated as soon as we landed in Bangor. The drive to the location we were staying was nothing short of gorgeous.

I truly believe Maine is the most beautiful state in America, and the only other state that can compete with it is Montana. Both are beautiful to a point that words can’t really describe.

More gorgeous scenery. (Credit: David Hookstead)

It became immediately clear to me that this trip was going to be epic (remember the part about doom mentioned above. We’ll get back to that), and it was like a shot of adrenaline to the heart.

We arrived at our hotel, and it was epic. It was also incredibly expensive, and at first, I was hesitant at the price tag when we booked it. The small community we were in had very few options, and that drove prices really high. It didn’t take long to realize it was money well spent.

Without getting into specifics for security reasons for some people we were with, I’m not going to name it but it was like walking into a time machine. This working class blue-collar man is getting a taste of the high life and I’m liking it.

The Friday night schedule was pretty simple. There was a boat ride around Moosehead Lake - a massive lake with scenery out of a "Yellowstone" episode - that included plenty of drinks and incredible food. However, the night didn’t end once the boat ride was over.

The entire wedding group hit up a local bar for the next four hours or so. To tell you how small of a world it is, I spent a couple hours talking to a retired air marshal, and it turns out we have a mutual contact from his time in the Marines that I know through my podcast. Very small world.

Do we go to bed after the bar shuts down? Nope. We decide to crush beers on the front porch of the hotel until the early morning hours swapping stories and reflecting on many different things. These are the moments money can’t buy. Who would have ever thought a kid from rural Wisconsin would find himself in the high society section of Maine? Life certainly can be funny at times.

Next up is the Saturday wedding, and I’m excited. I love weddings. Love them. I don’t care about the ceremony very much. What I care about is what everyone else cares about - the party.

However, the wedding didn’t start until 6:30 local time, and that meant we pretty much had an entire day to kill in high society Maine. What does a working class guy with free time on his hands do among the American elite?

The same thing I do when among my own people:

Find a place with great food and cold beer.

We end up at a small lakeside restaurant where I order some of the best biscuits and gravy that I’ve ever had. Most of the food scene in Maine revolves around seafood. Lots of lobster and crab cakes.

Why did I go with the biscuits and gravy? Simple. I hadn’t had it in a very long time, and simply had a scratch to itch.

My incredible biscuits and gravy. (Credit: David Hookstead) 

I also ordered a margarita at 9:50 am. I’m told this was an aggressive decision. I do not care. It’s a wedding day, and we might as well live high on the hog when surrounded by a part of high society I managed to sneak into for the weekend.

Is ordering a margarita in the morning too aggressive? (Credit: David Hookstead)

One of the observations I found myself constantly thinking throughout the day is that I couldn’t believe how safe I felt. I live in the Washington, D.C. metro area, and it feels like a war zone. The violence and carnage is out of control. I would never leave my door unlocked, and I constantly have my head on a swivel. I left our residence in Maine unlocked for the entire day, and didn’t think for a single second anyone would steal a thing. Why do I feel so safe in Maine, but not in our nation’s capital? Seems like something we should be able to figure out as a nation, and I made this point a handful of times. It was really neat to not have to worry about whether a homeless person would try to fight me or if bullets would come my direction. What a great change of pace! There were businesses that were literally on the honor system. You just take what you want, leave money and nobody is there to actually monitor it. What can we do to make more of society like that? Anyway, I digress!

A look at the honor system. (Credit: David Hookstead)

It didn’t take long until it was time to get ready for the wedding. You want to know how blue-collar I am? I do not know how to tie a bow tie, and this is the first tuxedo I’ve ever owned. It took a solid hour of attempts before my fiancée was finally able to get the bow tie looking crisp and tight.

After a cute ceremony, the party was on, and the alcohol setup was elite. As someone currently planning a wedding, I can tell you that making sure guests have plenty of options is a top priority. This couple (names withheld for security reasons) crushed it. One of the signature drinks was an espresso martini, which are awesome. I’m more than secure enough in my masculinity to admit it.

At one point a "Fight! Fight! Fight!" chant broke out, and I literally sprinted to the dance floor when the band started playing "Courtesy of the Red, White and Blue."

After more beers than I could count, it was time to load up and call it a night. Well, that turned into another porch session until 3:30 in the morning.

This trip couldn’t be going better. The wedding was one of the best I’ve ever been to, I looked great in my tuxedo, my fiancée rocked it and it was great to see so many close friends in one place.

I would share a photo of the people who were there, but people would probably think it was photoshopped. It felt like we had the heads of the media and government in one centralized location….and somehow this low class working man got on the guest list. What world are we living in?

Little did I know a disaster was right around the corner.

Travel disaster strikes.

I get woken up by Shelby in the early morning hours and am told our flights have been canceled due to bad weather. I look out the window. Bad weather? It’s sunny and 80 degrees out. Planes can’t fly in this weather all of a sudden?

To make matters much worse, there aren’t any realistic options. I could spend all day driving to Boston and hop a flight early Monday morning, I can hunker down and ride this out until flights resume Tuesday or I can try to get my hands on a private jet for emergency reasons and get the hell out of here.

A decision has to be made. Time is of the essence, and we do not have time to do nothing. I briefly wonder if this was the same feeling Obama got when he had to make a call on the raid to kill Osama bin Laden.

Maine has gorgeous views. (Credit: David Hookstead)

A decision is in. I make the call to go to Bar Harbor on the coast and ride this situation out until my now-least favorite airline decides it's time to go back to work.

What had been an incredible wedding trip is now on the verge of utter collapse. The weak would collapse. The scared would hesitate to make any decision.

Not me. Sometimes the only option on the table is to push through, and hell, if I fit in with one high society group, who's to say I can’t do it again?

That’s where we are now. Hunkered down in Bar Harbor until Tuesday, and I can’t wait to see how round two of "Hookstead meets rich people" goes.

Some other quick observations about Maine:

• I saw American flags everywhere. I couldn’t go anywhere without seeing American flags hanging from houses, stores and electrical poles. I loved it.
• I saw plenty of Trump signs. Didn’t see a single sign supporting Kamala Harris.
• People are way nice and way more relaxed than in Washington, D.C.
• Remember what I said safety? It’s stunning to me a short plane ride takes me out of the war zone of Washington, D.C. to a location where I never felt to lock the doors.
• I look great in a tuxedo. I’m not going to apologize for saying it.
• A photo booth at a wedding is a must. They had one, and it was a massive hit.
• Good luck getting solid cell reception in most of Maine. It's awful.

Overall, it was great to be surrounded by fellow patriotic Americans in a setting that you don’t often see kids from Randolph, Wisconsin end up in. I snuck into high society and loved it….and dare I say it loved me too? Even in the face of an absolute travel disaster, my spirit remains high and my resolve strong. I love Maine, and it’s now time to figure out what Bar Harbor is all about. Let me know what you think about Maine at David.Hookstead@outkick.com.