Life by Shelby Presents: Dating in the Workplace

Dear Shelby,
I enjoyed your column and thought you might be able to give some perspective on my current dilemma. Basically I’m falling for one of my co-workers but am not sure if it’s appropriate to pursue further. We’ve hung out in group settings outside of work a few times lately and really hit it off. I am one of two managers in a 20 person office so she is technically a subordinate, however the other manager is their direct supervisor. I know it would be easier to just avoid but I’d really like to take her out on a date to see if the connection is as strong as it seems.
Coworker in Love

Dear Coworker in Love,

Author Shelby Otto writes her column, Life by Shelby, for West Orlando News readers! Feel free to send in your submissions (see below) and Shelby will offer her honest, personal advice!

Dating in the workplace is a tough subject. You spend so much time with someone who you feel like you know them, flaws and all, which can be great to discover before dating someone. It can turn into something pretty awesome. It can also end in complete disaster. You’ll then be forced to see them at work, potentially causing tension in your office. The first thing you need to find out is whether her feelings are mutual. The worst thing you can do is to make advances on her when she doesn’t feel the same way.

The next step in this delicate process is to find out whether this girl is 100% worth dating. Not 75%, not even 98%. Let’s take a page out of the dating book. You can be interested in someone, go out on a couple dates and then if things fizzle out you can make a quick escape and move on, no harm done. If this happens with your coworker, there is no quick escape. There is a chance that someone could get hurt and now things are extremely awkward. You also need to be prepared for the repercussions if this relationship goes against your company policies.

The best thing you can do at this point is to get to know this girl as much as you can before deciding to date her. Learn her favorite color, what kind of music she likes, and continue to hang out with her in group settings (avoid drunken nights at ALL costs). You need to know whether her chewing noises bother you, or whether you both have similar future goals. If you mutually decide to go forward with the relationship, you need to have a serious conversation about what happens if it doesn’t work out.

At this point, you should be pretty good friends with this girl which is the most important step because if you know how to be friends before the relationship, you’ll already know how to be friends if it doesn’t work out. This can alleviate the tension in the workplace in the event that things go south. That’s not to say that things won’t still be really awkward for a while.

Now if you’re not willing to put forth this much effort for her, then it’s probably not worth pursuing. Good luck my friend, I hope this helps you make your decision.

Please email me at if you’d like some sincere advice on the current dilemma in your life! Or you can send an anonymous submission directly through our WON contact form and reference the Life by Shelby column.



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