In Love With The Man That Signs The Checks

by Vonda Howard

man with cashHey Vonda,

First let me say I love your column!  I have been reading them since the beginning and you always give such great advice!  Hopefully, you can help me with my little bit of drama.

I will get right to it…I’m in love, I mean head over heels, in love with my boss.  I know it sounds a bit cliche, but I am.  Vonda, he is like Morris Chestnut and Idris Elba all wrapped up in one tall, sexy, chocolate package.  Let me put out there that he is single (I am and will never be the other woman).

Now, I THINK he likes me too.  There has been flirting going both ways at after-work events and social engagements we have both attended, but there has never really been any action on anything.  There have been “secret admirer” gifts sent to me, and we get one another gifts every year for each other’s birthday.

Vonda, I dream about this man and often cannot concentrate because he is on my mind.  What should I do?  I want to approach him and see if he wants to go out on a date, but I don’t want to look like an idiot if I’m wrong.  Help!!

In Love With The Man That Signs The Checks

Dear In Love With The Man That Signs The Checks,

First, thank you so much for the awesome compliments!  I really appreciate the love.

Now, let’s get to your drama.  It’s great that you found someone that makes your heart go “pitter-patter”.  Everyone deserves that, but I would say to tread lightly on this one.  You said that you THINK he feels the same about you.  That little bit of doubt can make a huge difference not only in your job, but whether or not you get humiliated.  The fact that in this long amount of time he has NEVER acted on any (of what you may perceive as) flirtations says a lot to me.  I would not suggest you approaching this head on unless you are sure without a shadow of a doubt that he feels the same way.  Are you sure you’re not looking too deep into any of it?  You can’t really say the secret admirer gifts are from him, unless he revealed it was him and birthday gifts can be just that…birthday gifts.

As it stands on office romances in general, I tend to lean on the “stay away” side.  What happens if the relationship crashes and burns?  It will certainly create a hostile and uncomfortable working environment for the both of you.  Again, the fact that nothing has been acted on may signal that even if there are feelings or attractions involved, he know that this would just be an inappropriate situation if it went any further. I know this is probably not what you want to hear, but trust me, I’m saving you a lot of heartache and embarrassment.  Outside of you finding another job and THEN approaching him, I REALLY don’t think its a good idea to pursue any type of romantic relationship with your boss.

Good luck to you!!


About the Author: Vonda Howard is the author of the new hot book series, The D-Cup Divas™, a graphic designer of her own graphic design firm, Cupcake Creative Studio, mom to two, wife to her one and only and a domestic goddess (not really…LOL). She does not profess to be an expert, but just that one opinionated girlfriend you go to for the straight nitty-gritty. So just relax and enjoy. ;o) Do you have a question? Send it to this and you may get featured!

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