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32YO Man Confused After Female Boss Invites Him On All-Paid Vacation, The Internet Is Very Divided
Smiling woman in business attire talking on phone in hotel room, reflecting on blurred lines and vacation with boss.

32YO Man Confused After Female Boss Invites Him On All-Paid Vacation, The Internet Is Very Divided

Interview With Expert

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Most folks have experienced what a good boss is like and what a bad one can be like, which is why people mostly prefer to work with nice managers and leaders. Sometimes, when people are close friends with their bosses, the line can get blurred and it becomes hard to know how exactly to behave around them.

This is what a man experienced when the owner of his company asked him to join her on a non-work trip to Mexico. Since she just sprung the plan on him, he wondered whether to go or if it would create unnecessary drama.

More info: Reddit

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    Boss inviting vacation with her, smiling woman in business attire talking on phone while sitting on hotel bed.

    Image credits: stefamerpik / Freepik (not the actual photo)

    The poster shared that his boss is bad at separating her work life from her personal life and that she has always been very friendly with everyone

    Text excerpt discussing a boss who invites an employee on vacation, highlighting blurred boundaries between work and personal life.

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    Text excerpt describing a boss invite vacation with her, mentioning a fully paid trip to Mexico not related to work.

    Frustrated man at office desk with laptop looking stressed while two women in background discuss boss invite vacation with her.

    Image credits: freepik / Freepik (not the actual photo)

    One day, the boss randomly asked the poster if he would join her on a paid non-work trip to Mexico, but he was shocked by the request and didn’t know what to say

    Text describing someone unsure about a boss inviting them on a vacation, clarifying no flirting or romantic intent.

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    Text expressing uncertainty about a boss invite vacation with her, appreciating the boss and job but unsure what to do.

    Man sitting on floor next to yellow suitcase, looking thoughtful while holding travel documents before boss invite vacation with her trip.

    Image credits: prostock-studio / Freepik (not the actual photo)

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    The man didn’t think his boss was hitting on him since she has an on-and-off-again boyfriend and has not implied anything like that

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    Text excerpt discussing a personal story about the boss invite vacation with her and past relationships.

    Image credits: anonymous

    The poster also clarified that he does find his boss beautiful, but he isn’t interested, as he has never slept around since losing his wife five years ago

    Right from the start, it seems like the company’s owner is on quite friendly terms with all of her employees. She doesn’t seem to have a problem with creating overlap between her professional persona and her personal life. That’s probably why she thought it would be okay to ask the OP to join her on vacation.

    According to experts, a friendly boss can help foster a pleasant work environment and make people feel comfortable. On the flip side, being too casual can cause interference with professional matters and lead to concerns about favoritism. Therefore, the leader must maintain a balance so that their behavior doesn’t cause conflicts in the workplace.

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    To get a better insight into this situation, Bored Panda reached out to Wendy Sellers, also known as the HR lady. Apart from being a consultant, speaker, and educator, she is also the author of HR and management books. Wendy said that “generally, it’s not appropriate for employees to vacation with their boss because it blurs professional boundaries.”

    She also mentioned that it “can create perceptions of favoritism and may expose both parties to ethical or legal risks. If they’re genuinely close friends outside of work, it’s still wise to be cautious about trips like this because perceptions matter in a workplace. Even with a real friendship, coworkers or higher management may assume favoritism or conflicts of interest.”

    Boss invite vacation with her, smiling woman in blue shirt talking on phone at office desk with travel plans nearby.

    Image credits: freepik / Freepik (not the actual photo)

    Even though the poster was wary of his manager’s vacation offer, he was torn because it meant he’d get a free trip that would probably be enjoyable. He asked folks for advice because he didn’t know what would happen if he actually accepted her offer and travelled with her to Mexico.

    Wendy Sellers clarified that “if the man accepted the offer, it could lead to workplace gossip, damage his credibility, and potentially compromise his career growth or objectivity in performance evaluations. The ‘boss’ needs to ensure she is always holding all of her employees, including this man, accountable for their job responsibilities, no matter what their friendship status is.”

    Another important thing to note is that, even if people do go on trips with their boss, professionals say that they should always behave in a refined way. That means that they shouldn’t let their guard down with their manager or act in an overly casual manner. 

    Therefore, it seems like even if the guy did travel with his boss, it would probably be a tiresome experience where he’d have to put on a ‘professional’ act. Although the offer of a paid trip does sound inviting, is it truly worth it? 

    Would you take up an offer like this from your boss? Be honest with us and let us know your opinion of this story in the comments.

    Netizens were divided, with some feeling that it would be a bad idea to go, and others thinking there would be no harm in his accepting the offer

    Comment on a forum post discussing taking an opportunity, relating to boss invite vacation with her context.

    Screenshot of a social media comment about a boss inviting her on vacation, offering to go in her place.

    Text comment on a white background reading woman calling boss naive and backup plan in a casual online discussion about a boss invite vacation with her.

    Boss invite vacation with her message displayed on a screen with a comment about corporate life and challenges in the background.

    Comment about a tan and a person named Jan, posted 5 days ago with 52 points.

    Text post on Reddit discussing negative views and advice regarding interactions with women, related to boss invite vacation with her.

    Screenshot of an online comment asking a question related to boss invite vacation with her topic.

    User comment on a forum discussing getting paid to vacation and having a bold interaction with their boss.

    Text excerpt discussing a situation involving a boss invite vacation with her, mentioning room sharing and a possible mix-up.

    Person typing on a laptop with text about flipping letters, representing boss invite vacation with her concept.

    Comment on a forum expressing doubt about the idea, mentioning it may not be a good plan.

    Comment warning against going on a vacation with a boss who has problems with boundaries, advising caution for livelihood safety.

    Poll Question

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    Beverly Noronha

    Beverly Noronha

    Writer, BoredPanda staff

    Read more »

    You can call me Bev! I'm a world-class reader, a quirky writer, and a gardener who paints. If you’re looking for information about tattoos, Bulbasaur, and books, then I'm the NPC you must approach.

    Read less »
    Beverly Noronha

    Beverly Noronha

    Writer, BoredPanda staff

    You can call me Bev! I'm a world-class reader, a quirky writer, and a gardener who paints. If you’re looking for information about tattoos, Bulbasaur, and books, then I'm the NPC you must approach.

    Denis Krotovas

    Denis Krotovas

    Author, BoredPanda staff

    Read more »

    I am a Visual Editor at Bored Panda. While studying at Vilnius Tech University, I learned how to use Photoshop and decided to continue mastering it at Bored Panda. I am interested in learning UI/UX design and creating unique designs for apps, games and websites. On my spare time, I enjoy playing video and board games, watching TV shows and movies and reading funny posts on the internet.

    Read less »

    Denis Krotovas

    Denis Krotovas

    Author, BoredPanda staff

    I am a Visual Editor at Bored Panda. While studying at Vilnius Tech University, I learned how to use Photoshop and decided to continue mastering it at Bored Panda. I am interested in learning UI/UX design and creating unique designs for apps, games and websites. On my spare time, I enjoy playing video and board games, watching TV shows and movies and reading funny posts on the internet.

    What do you think ?
    sweet emotion
    Community Member
    2 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Having just sat through the annual anti-harassment training at work, I can say that the boss' request is absolutely inappropriate (at best) and should be reported to HR or her manager immediately. Also, any retaliation on her part would be illegal in the US. If the company ignores or buries the complaint, outside counsel may be necessary.

    Dusty's mom
    Community Member
    2 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Boss own her own company. No one to report her to.

    Load More Replies...
    Melissa Harris
    Community Member
    2 months ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    Guys going to end up without a job eventually no matter what. It's a loss-loss situation. If he goes and rejects her sexual advances she's going to find a reason to sack him. If he declines he's going to be sidelined and at the top of the list for the next round of layoffs. If he sleeps with her he better be ready to get sacked the moment their relationship becomes public. He needs to start documenting the sexual harassment (this is what this is) and consult an employment lawyer. Hell, the inappropriate invitation alone if documented is grounds for a lawsuit.

    Nina
    Community Member
    2 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Even if he goes and nothing happens, their coworkers will assume something happened. Going on vacation with your boss blurs work-private boundaries way too much.

    Load More Comments
    sweet emotion
    Community Member
    2 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Having just sat through the annual anti-harassment training at work, I can say that the boss' request is absolutely inappropriate (at best) and should be reported to HR or her manager immediately. Also, any retaliation on her part would be illegal in the US. If the company ignores or buries the complaint, outside counsel may be necessary.

    Dusty's mom
    Community Member
    2 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Boss own her own company. No one to report her to.

    Load More Replies...
    Melissa Harris
    Community Member
    2 months ago (edited) Created by potrace 1.15, written by Peter Selinger 2001-2017

    Guys going to end up without a job eventually no matter what. It's a loss-loss situation. If he goes and rejects her sexual advances she's going to find a reason to sack him. If he declines he's going to be sidelined and at the top of the list for the next round of layoffs. If he sleeps with her he better be ready to get sacked the moment their relationship becomes public. He needs to start documenting the sexual harassment (this is what this is) and consult an employment lawyer. Hell, the inappropriate invitation alone if documented is grounds for a lawsuit.

    Nina
    Community Member
    2 months ago Created by potrace 1.15, written by Peter Selinger 2001-2017

    Even if he goes and nothing happens, their coworkers will assume something happened. Going on vacation with your boss blurs work-private boundaries way too much.

    Load More Comments
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