In the clip, the man can be seen showing the woman his online bank account with Wells Fargo, in which he has more than $92,000 (£66,603). But pleasingly, his sizeable savings seem to do nothing to woo the woman.
She says: "You really think that that is gonna impress me?"
He replies: "It should."
However, it's clear that the guy is barking up the wrong tree here, as our Shania Twain-like hero has got no time for his boasting.
She says: "Money doesn't f*****g impress me. I'm sorry, it does not impress me."
At this point, rather than apologising and feeling all humiliated about his arrogant, failed attempt at pulling, the guy decides to double down - well and truly ensuring that this woman will never be impressed by him.
He says: "Then you lost in life... $92,208."
I'm not sure about that mate, seems pretty clear which one of you was losing in life right here.
The people of Reddit were in no doubt either, with a decisive 98 percent of respondents in a poll voting it 'cringe'.
Commenting on the video, one person said: "This feels like he just got a personal injury settlement pay-out and thinks 'I'm rich now b*****s'.
"Everything about this screams 'sudden cash' for a person who's usually financially unstable."
Another said: "'You're lost in life' that's rich coming from a guy who has so few attractive qualities that he can't even get people interested in him with money."
A third added: "Bragging about money reduces your attractiveness factor by at least 75 percent. Just shut the f**k up and be a good person."
Beyond the undeniable cringeworthyness of the interaction, others argued that his antics made him look more like an idiot than a success story.
One Reddit user wrote: "Keeping 92 grand in a checking account is idiotic. Poor guy clearly doesn't know much about personal finance.
"Edit - to all of you who are asking why this is bad: checking accounts accrue no interest so having a large amount of cash in checking is just leaving thousands of dollars per year on the table for this guy.
"Especially considering that if you're the type of person to show off 92k at a bar it is likely all of your liquid assets. Keeping that in stocks/bonds, mutual funds, even savings accounts are all better options.
"If this man had kept that money in a total market ETF for the year, he could've bought the whole bar out for the night on just the earnings. Then maybe he'd have gotten laid, and been put on Reddit as 'awesome guy who buys whole bar drinks because he is really smart with money', instead of 'cringiest guy in Reddit so far this year'."
Featured Image Credit: Reddit