Lifestyle Sharing the Struggle

Sharing the Struggle: What if? Or maybe no regrets!

Dear June,

I have a huge crush on my co-worker. I’ve liked him for about two months now. We hang out everyday during lunch with our other work friends. However, I am moving soon. I want to tell him how I feel but, at the same time, he’s my co-worker and it’s not appropriate. Plus I don’t want to risk ruining a good friendship. And what would be the point? I’ll be leaving anyways. Help, please!

-Tortured in Tokyo

My editor has informed me that I am not allowed to refer to you as “TIT,” which would be customary for this column, so I will henceforth refer to you as “TNT.”


I am a huge fan of letting love in, with few exceptions.  If this man is your superior or your subordinate I say absolutely do not tell him how you feel while you still work there.  You will open yourself up to the potential for unwanted HR attention.  You also mention that you are moving but you don’t state how far.  For the sake of this article, I am going to make the assumption that this man is your peer and you are moving far enough away that an intimate relationship would be next to impossible.  

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Let’s break this down into the limited possibilities.  Let’s say he likes you.  Now you will move away wondering what the relationship could have been if you had stayed.  What if you aren’t that lucky?  You have altered the friendship you value so much, at least for the time being.  Are you prepared for either outcome?  Awkwardness can’t be part of your decision to tell him, because of course things will be awkward.  I promise, the awkwardness will fade within a week.  

If you weren’t moving, I would say go for it.  When it comes to finding love post-college, work is one of the only chances you have to meet someone organically.  Since you are leaving, my advice is to phrase it in such a way that you let your feelings be known without the expectation of a response.

Studmuffin (insert his actual name here), I have enjoyed our time together for the last X months.  The more we got to know each other, the more I could see myself with you.  I would like to think that should our paths ever cross again that we could grab a drink and see where things go.”

Live your life with no regrets.  If you know you will always wonder “what if” if you don’t tell him then, TNT, you know what you have to do.  So, go get your nails done, buy an outfit that makes you feel confident, put on said outfit (don’t do this naked because results may vary) and tell the man.

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Best of luck,

June Spence

P.S. TNT, please keep us posted on how this turns out.

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About June

June was born and raised in the south where “bless your heart” is an insult. Self professed serial dater and an expert in all matters of the heart. June also enjoys volunteering, dancing and sewing.

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