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A Woman Was Set Up on Blind Date By Her Boss, And Things Took An Unexpected Turn

When it comes to blind dates, there’s always an element of mystery; that’s kind of the point! You don’t know who you’re going to get until they’re standing right in front of you. But Olivia Fenton’s blind date experience reached a whole new level of unexpected. The New York singleton was ready to take a leap of faith to find a match, but she wound up on one of the weirdest, most perplexing blind-date sagas imaginable.

An interesting proposition

In late January 2022 Olivia posted a video to her TikTok account that quickly racked up a mind-boggling 3.9 million views. It begins with a quizzical Olivia — a singer and an actress — posing a question to the camera: “Does anyone else have a manager who came into work, told you she wanted to set you up with her best guy friend?” Nothing too out of the ordinary there, but this is just the beginning of Olivia’s story.

Modern dating is tough

New York is a city absolutely filled to the brim with people — almost 19 million, in fact. But while there’s plenty of fish in the sea, the dating scene has arguably never been harder. On top of the usual avenues like hitting their local bars and clubs, most singles use dating apps or speed-dating events to try to find that special connection. Unfortunately, for some people, it can still prove frustratingly elusive in spite of all these options.

Deciding to go for it

Perhaps this is why Olivia agreed to let her boss set her up with her eligible bachelor best friend. She was open-minded and keen to try something new — not to mention impressed by how hot the guy was when she was shown his photo! So, she let her boss put her in contact with the mystery man, and they arranged to meet for a first date.

Everybody deserves a second chance

When Olivia showed up for the date, though, she wound up sitting alone. That’s right — the guy stood her up! No doubt feeling upset and betrayed, she went home, but soon received a text from the apologetic no-show. He tried to convince her to give him another chance and, knowing how sometimes plans can genuinely go awry, she gave him the benefit of the doubt.