Boyfriend age 39 still pulling this stunt
The boyfriend who secretly brought his friends on a paid trip his girlfriend was funding was 39 years old, which the hosts found especially egregious.
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Around The World In 60 Minutes | Reading Reddit Stories
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Jul 4, 2026
Where this was said
My bf brought his friends on a road trip unannounced
At 27:27 · chapter starts 18:47
Shayne introduces the second story from Am I the Asshole (September 2022): a 30-year-old woman's boyfriend, Smith, aged 39, has been repeatedly asking to bring his two friends on a road trip she's paying for with her own car. He promises to drop it, and she agrees to pick him up — only to arrive and find him standing outside with his friends and all their bags, fully expecting her to comply. She doesn't stop. She turns around. He chases after her car on foot. [1] — Shayne Topp "A woman drives to pick up her boyfriend for a road trip she's funding, spots him outside with two friends and all their bags — uninvited, a…" 21:20 The fight that follows includes him accusing her of acting immaturely and demanding she apologize for embarrassing him in front of his friends. The hosts are uniformly stunned that a 39-year-old is behaving this way, with Shayne suggesting this isn't a one-off red flag but an unchangeable character trait. Ian and Amanda both note the inability to respect someone's 'no' signals he may not actually like her — and is using her financially. A perfectly-worded Reddit comment closes it out: 'recommend you keep this guy in the rearview mirror.'
Girlfriend paying for all trip expenses
The OP was paying all expenses AND providing her car for the road trip, making the boyfriend's secret friend invite even more exploitative.
The Silent Turn-Around That Spoke Volumes
A woman drives to pick up her boyfriend for a road trip she's funding, spots him outside with two friends and all their bags — uninvited, after repeated explicit promises — and simply keeps driving without stopping. He chases after her car. The hosts are unanimous: this is the correct response to someone who agreed to your terms and then violated them anyway.
He's 39 and Doing This
The hosts are particularly stunned that the road-trip boyfriend is 39 years old. Shayne points out the behavior — lying to sneak friends onto a trip his girlfriend is paying for, then accusing her of acting immature — signals not just a red flag but an unchangeable character pattern. Ian adds: if he's doing this at 39, it's never going to change.
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