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Dating a coworker that dated a friend


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Posted

Help me out here, oh wise people of The Shack.

 

Should I run for the hills or pursue this woman?

 

I am a recentlyish singled 34 year old male. I've gone out on a handful of dates with a coworker. I know what you are going to say "Don't dip your pen in company ink." For the record, the pen is only hovering over the ink so far. :D

 

She is in her late 30's, attractive, smart, charismatic, and very professional. We connect very well and spend our time together laughing and having a great time.

 

There are a couple minor issues, aside from her being a coworker. She dated one of best friends/coworkers. He has since moved on and is dating someone new.

 

My heart says, go for it bro. She has all of the qualities of someone I could settle down with. I'd be lucky to date someone of her caliber. What if I regret not giving it a chance?

 

My head says, easy there buddy. You are playing with fire. Imagine things go sour and you have to face her at work every day. That would kill you slowly.

 

What do you think?

Posted

Do not mess with or try to date the women you work with. You might end up in trouble. Date women outside of your workplace. There are 1000's of them to choose from.

Posted

Working with you is bad enough, but having dated your best friend who also works there could also cause problems. I've dated a coworker before so I do know it rarely ends well. With those 2 red flags, I'd look elsewhere, but as long as you understand you may lose your best friend and may have to look for another job or transfer if things don't work, then go for it.

Posted

Once when I was in my mid 20's I dated a woman I worked with. Never again. Terrible mistake. Having to see and work alongside somebody every day that you were sleeping with then broke up with who's not happy with you is awful.

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Posted
Once when I was in my mid 20's I dated a woman I worked with. Never again. Terrible mistake. Having to see and work alongside somebody every day that you were sleeping with then broke up with who's not happy with you is awful.

 

That is my ultimate fear. I couldn't imagine how awful that could be.

 

Thank you for the advice. I appreciate you taking the time to respond.

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