Disclosure: This post may contain affiliate links, meaning if you decide to make a purchase via my links, I may earn a commission at no additional cost to you. See my disclosure for more info.
In Bill Bryson’s excellent book A Walk in the Woods, he attempts to walk the entire Appalachian Trail, joined by his erratic buddy Stephen Katz. Katz is unprepared for the trek ahead and struggles with much of the trip. A recent online post reflects on travel experiences people have had with their Stephen Katz-like friend, who constantly needed money, played the guilt card when they couldn’t afford anything, and sucked all the fun from the trip. Here are Risky Retreats: Adventures in Unplanned Spending on Vacations
Loan What You Can Afford

A good rule for traveling with a broke companion is only lending them an amount of cash you will be willing to waive — chances are you won’t see it again. One story involves a travel companion putting his friend on the spot by asking for a holiday money loan after arriving at their destination. The storyteller refused, saying he knew the money would be gone forever and didn’t want to lose a friendship. His travel buddy wasn’t pleased.
Kindness Goes a Long Way

A group of friends treated their unemployed friend to an all-inclusive Cuba holiday, though he refused their invite on excursions, as he was already grateful enough. Thankfully, the kindness they showed and his guilt at missing the excursions motivated him to make a positive change. Once he returned to America, he turned his life around and started a successful career.
No Pay, No Play

To keep the peace, some people have a no-nonsense approach to friends who come unprepared on vacation. Tough love is sometimes necessary, and hopefully, it will spark the friend into organizing their finances better. However, some friends genuinely need help or may be going through a tough time — it all depends on who they are.
What Goes Around

True friends understand each other well enough to know when one of the pack needs lifting. Some friends would do the same for you, so why not spread the love if you can afford it? That is what friendship is all about. The lesson here may be to avoid traveling with lesser-acquainted colleagues.
Choose a Suitable Location

If you know your travel friend is experiencing financial hardship, maybe a VIP experience in Ibiza is off the cards. If there is a financial rift between the two parties, why not lower your budget instead of putting pressure on theirs? A long weekend at a national park can be more rewarding than an all-expenses Cabo journey.
No Hard Feelings

A wealthy American professional moved to Europe, inviting his best friend, who left behind his entire life in the States, to join him. He has no money, but the poster doesn’t care, stating that his company means more than any money, so he happily funds their adventures as he looks for work. Paying a little extra to have your wingman join you for your dream adventure; can you even put a price on that?
Sometimes, You Are the Stephen Katz

Spare a thought for the friend who booked the trip but faced an unexpected or sudden financial hardship — maybe they lost their job, had to pay for funeral costs, or their car was totaled. No matter how graciously your companions help you with money abroad, it can’t feel empowering.
The Joneses

A married man recalls how he and his wife tried to keep up with his wealthy friends while she was finishing her degree, and he was a new graduate. The friends were all established, affluent professionals who invited the couple to Tuscany one summer. The commenter explains how they put themselves into financial trouble, though they opened their eyes to the lifestyle they wanted — which, sadly, didn’t include five-star hotels in Florence.
You Didn’t Give Me a Chance

One story involves a needy friend being shady about how much money they had saved before the trip began, then revealing how broke they were once they arrived. Subsequently, she complained when the group chose mid-priced restaurants, joined on excursions but sulked about the price, and complained that nobody gave her enough time to save up for the trip — six months.
Be Upfront

If a friend suggests going away somewhere, maybe the best option is to be upfront about everything. If you feel they are not at their financial best, a better idea would be to suggest a cheaper or shorter adventure somewhere — an overnight mountain biking tour, a staycation in your city, or visiting a mutual friend’s place for a night instead.
Source: Reddit.
Generational Shift: 18 Classic Cars Loved by Boomers, Snubbed by Millennials

In the world of automobiles, some cars are timeless, forever etched in the minds and hearts of those who drove them. But generational shifts in taste and values can lead to once-beloved vehicles being relegated to the shadows. Let’s revisit 18 classic cars adored by Baby Boomers but often overlooked by Millennials.
Generational Shift: 18 Classic Cars Loved by Boomers, Snubbed by Millennials
From Boom to Bust: 18 States on the Brink of Financial Ruin—What Went Wrong?
We’re embarking on a financial roller coaster ride through 18 states, and it isn’t the fun kind. We’re talking about states having to check under the mattress and behind the couch cushions for extra change. These states are trying to balance their budgets, but the numbers aren’t increasing. Why are they skimming through their wallets like they lost a 20-dollar bill? Let’s find out!
From Boom to Bust: 18 States on the Brink of Financial Ruin—What Went Wrong?
Avoid These 19 Pointless Expenses When Living Paycheck to Paycheck

Living from paycheck to paycheck puts one in a dangerous financial bind. It’s more prevalent than you can imagine. According to a survey by CNBC, more than half of all Americans (58%) live paycheck to paycheck. When money is tight, it’s crucial to pinpoint and cut out wasteful expenditures that eat away at your hard-earned savings.
Avoid These 19 Pointless Expenses When Living Paycheck to Paycheck