If the error seems very solvable, it often is. Unless, according to Kennedy, you book with online travel agency Expedia.
In a TikTok, Kennedy said the mistake was made by Expedia and was the reason he missed out on his celebration.
"My friends and I booked as a group and [Expedia] asked for our first, middle and last name, totally normal," he said.
"But somehow in the back end of their system, they removed the space between my middle name and my last name. So, my ticket doesn't match my passport anymore."
In the US, all travel documents must match official ID exactly, or else you will not be allowed to board a flight.
Since being posted 3 days ago, the video has amassed more than 1.3 million views.
According to Kennedy, not even WestJet, the airline he was flying with had the power to undo Expedia's mistake.
The bachelor was allegedly told by a WestJet agent that, since Expedia revokes access to airlines, they could not change passenger info for their own flights.
No information is available about this on Expedia's website.
"People have to call [Expedia] and pay them a whopping $65 per letter," Kennedy said in the TikTok.
"I woke up at 4 am to wait in check-in for two hours because of your mistake; stayed on hold with your support team for over an hour because of your mistake, and now don't even get to go to my own bachelor party because of your mistake, so f**k you Expedia."
Kennedy told Canadian news site Daily Hive he then received an email and a direct message on Instagram from Expedia stating they would investigate the issue.
"30 minutes later I received another email from the same address saying '[Employee Name] would like to recall the message,' " he explained.
Other travellers commented on the TikTok saying they had similar experiences and never resived a refund.
"I do want my money back, of course, but I'm not holding my breath," he said.
"Honestly, I think I just want them to apologize to my friend who spent so much time planning what would have been an amazing trip for me, and for Expedia to acknowledge their mistakes publicly because they're actively ruining what are meant to be lifelong memories for so many people."
The group attempted to find another flight, but knew "airports are miserable right now" and Kennedy was exhausted from dealing with the stressful situation.
Instead, he spent what would have been four incredible days in Vegas, at home, drinking with his dog and inviting followers to join a virtual bachelor party.
Kennedy may be disappointed and angry at Expedia but also felt it was important to be kind to employees working as customer service agents.
"Please remember, these people aren't the ones setting these greedy policies," he said.
"Nobody likes being the person that has to tell someone they can't go on their vacation, so as much as you can please try to temper your emotions and understand who to truly direct your anger at."
