Entitled job applicant lands interview, demands job because dad dated boss's sister: 'You might remember my dad'

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Ally Perry • Writer and Editor
Feb 8, 2026 9:00 PM EST

It's often said that professional success is down to who you know, not what you know.

There is a reason that professionals from all sectors make a big deal about forming relationships and making connections when advising those who want to get into their industry. The fact of the matter is that the working world is rarely fair, and a little networking can get you a long way when it comes to exploiting that. Keeping in touch with people counts for a lot, and can set you up with opportunities that you might miss otherwise.

That being said, forming these kinds of relationships is just as much of a skill as anything else on your resume. It requires a certain level of strategy and tact, which does not come naturally to everyone when they are doing their best to get ahead. Just like anything, networking involves a level of risk, and it can backfire massively when you get it wrong. Not everybody appreciates being the audience to somebody's desperate attempt to sell themselves, even if it relates to their career. What's worse is that this attempt to form a connection can come off as entitled, which is not going to go down well.

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  • a man in a suit holding a pen with papers in front of him speaks to a woman sat opposite him
    via Getty Images (Unsplash+)

    The image does not depict the actual subjects of the story. Subjects are models.

  • These days, getting to the interview stage of a job opening is no small achievement. It makes it even more important that you do your best not to mess it up. One manager was taken aback by a recent job applicant after a comment he made towards the end of his interview.

    Although this interviewee had given a positive impression in the first half of the interview, he jeopardized this later on when he claimed that he should be given the job because of his personal connection to the interview. His dad had dated her sister when she was in high school.

    He didn't get the job, even though he begged for it afterwards. He had to learn a lesson in being humble.

  • Son of my boss's sisters ex says he’s entitled to a job

    When my company recently was hiring for three new managers one guy we'll name Colin came in for an interview.
    via Gymtrio2025
  • During the interview according to my boss Colin was very professional and showed promise until he said to my boss, "By the way I'm 'insert name' son, you might remember my dad he dated your sister in high school." My boss paused and remembered who he is referring to and said, "So you're expecting me to hire you because of an old connection your father has to my family?" Colin smiled and said, "Not expecting I'm entitled to it because we both know people in common." My boss said she'd let Colin k
    via Gymtrio2025
  • My boss sees Colin's father all the time in the gym when he comes to workout so she planned to talk to him about if he put his son up for saying their connection with each other.
    via Gymtrio2025
  • In the end Colin didn't get the job and tried pleading for a job but he still didn't get it.
    via Gymtrio2025
  • a man in a suit with a clipboard in front of him speaks to the woman sat opposite him
    via Getty Images (Unsplash+)

    The image does not depict the actual subjects of the story. Subjects are models.

  • PlausibleCoconut Connections but no brain or social skills
    via PlausibleCoconut
  • Gymtrio2025 Original Poster's Reply Reading my mind
    via Gymtrio2025
  • Tony-Flags I mean, personal connections have gotten me an interview before (that's how lots of people get jobs), but a sane person doesn't expect that you just automatically get the job. This is either a fantasy, or a moron thinks that's how hiring works.
    via Tony-Flags
  • Gymtrio2025 Original Poster's Reply Colin is definitely a moron for thinking that's how hiring works
    via Gymtrio2025
  • WeirdPinkHair I bet when your boss tells Colins dad what he said, his dad will groan and say 'where did I go. wrong with that boy'. And Colin will get an earfull.
    via WeirdPinkHair
  • Gymtrio2025 Original Poster's Reply I was told the two talked but the exact reaction of the dad is not known to me
    via Gymtrio2025
  • woodsman775 Doesnt even really have connections. At least not good ones!
    via woodsman775
  • TheQuarantinian I am your father's brother's nephew's cousin's former roommate
    via TheQuarantinian
  • LovelyLilac73 Yeah, that's not exactly how "leveraging connections" works, Colin...
    via LovelyLilac73
  • Weedster009 I can't believe that "My dad boned your sister" didn't get ol' Colin the job!
    via Weedster009
  • StructEngineer91 That also means the person you are interviewing with actually knows of your connection, meaning it is an active and likely meaningful connection.
    via StructEngineer91
  • TheGypsyThread Kid was lucky he didn't burst out laughing and send him on his way
    via TheGypsyThread

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boss manager work applicant workplace job interview dating entitled people
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