October 24, 2025 at 6:15 am

His Elderly Friend Invited Him On An All-Expenses-Paid Trip With Her, But Then She Made His Life Horrible By Expecting Him To Be Happy All The Time

by Liz Wiest

commercial airplane taking off

Source: Pexels/Reddit

Fewer things can make or break a friendship than traveling together as a pair.

How would you handle figuring out the hard way that you and your best friend were not compatible travel companions?

One man recently asked Reddit for advice on how to save his friendship after a particularly bad trip.

Here’s what went down.

AITA for not being constantly happy on a vacation I did not pay for?

I 38m was invited on a vacation by a dear friend 78f.

At first I was told that she would pay for everything as she had planned to take another friend on the trip.

The friend had to drop out of the plan.

Hate it when that happens.

Dear friend did not want to travel alone as she has mobility issues (uses a cane and has particular trouble with stairs) and wanted someone with her as she has fallen a couple of times this year and has a major surgery scheduled for later this year.

The vacation included a number of plays that she bought tickets for.

I do not particularly like the plays she chose nor did I have any input on the ones she chose.

I did not pay for any tickets.

However, she enjoys them greatly and I wanted to support her to the best of my ability.

Doesn’t mean you’re automatically going to like the plays.

One of first arguments we had was over what time to meet up on the first day.

Dear friend had told me 8:30am but called me at 700am expecting me to come immediately.

It was not an emergency or anything like that she just changed her mind.

I felt bad because I trusted her words.

Seems like these two haven’t communicated their expectations.

The next argument we had was over food.

I need to eat three times a day.

She exists off of coffee and one small, to me at least, meal at night.

She sounds like an enigma.

She would not stop and let me buy myself food instead insisting I eat the items she brought.

I do not particularly like those items.

Anytime I bring up a restaurant, she said she felt pressured to eat and that it would make her sick.

I never meant to pressure her into eating.

She then chose another restaurant, and ordered a sandwich.

Different eating schedules can throw a whole trip off.

I paid of course I am not a total lout.

The rest of the trip I managed to find a smoothie shop that worked really quickly while she occupied with shopping.

Tonight she got upset that I was not enjoying the plays.

I mean they are nice, but not my thing.

I’m sure he tried to be a good sport about it.

I try to talk to her about them or works by the same authors but she seems agitated when I try.

I am just lost on how to make her happy…

AITA?

Seems like this one was really just two people trying their best. Let’s see if Reddit agreed.

Many pointed out the unfair setup.

Screenshot 2025 09 23 at 7.24.27 PM His Elderly Friend Invited Him On An All Expenses Paid Trip With Her, But Then She Made His Life Horrible By Expecting Him To Be Happy All The Time

Some felt it should be water under the bridge.

Screenshot 2025 09 23 at 7.24.52 PM His Elderly Friend Invited Him On An All Expenses Paid Trip With Her, But Then She Made His Life Horrible By Expecting Him To Be Happy All The Time

A few were able to see both sides.

Screenshot 2025 09 23 at 7.26.41 PM His Elderly Friend Invited Him On An All Expenses Paid Trip With Her, But Then She Made His Life Horrible By Expecting Him To Be Happy All The Time

But others pointed out valid concerns.

Screenshot 2025 09 23 at 7.27.51 PM His Elderly Friend Invited Him On An All Expenses Paid Trip With Her, But Then She Made His Life Horrible By Expecting Him To Be Happy All The Time

Though some weren’t as forgiving.

Screenshot 2025 09 23 at 7.28.38 PM His Elderly Friend Invited Him On An All Expenses Paid Trip With Her, But Then She Made His Life Horrible By Expecting Him To Be Happy All The Time

It’s important to remember not all trips are vacations…

If you liked that story, check out this post about a group of employees who got together and why working from home was a good financial decision.