How To Ask Out a Co-Worker

The dating world is tricky.  As you get older, your friends start to get married and the pool of eligible partners shrinks dramatically.  Naturally, you will find yourself spending more and more time with people you work with, and less with friends.  The average American spends 45 hours per week at the office, which I would assume is far more than any of you spend with your friends.  This will lend itself to inter-work mingling.  Where some might say not to dip your pen in company ink, I say, go ahead! Dip away.


As long as you do things the right way, a work relationship can be fantastic.  There is no reason why a perfectly suitable mate that you meet at the office can’t turn into a fantastic partner.  The first step however is to make friends with this person first.  I know it sounds hokey, but making friends with someone is the best way to pre-qualify them as a good partner.  When jumping into the world of work dating, you do not, and I repeat, DO NOT want to go for anything but quality, and potentially long-term relationships.  Developing a reputation as the love em and leave em guy or gal at work is bad in more ways than I can describe.  Just don’t do it.


So now you’ve managed to strike up a friendly relationship with the boy or girl who you’ve had your eye on.  When do you make the move, and how?  Good questions.  It is preferable to make the approach outside of work.  See if they would be interested in grabbing a drink on a Thursday evening, or a quick lunch one day.  You definitely don’t want to corner them in the coffee room and ask for a date.  Awkward, awkward, stupid. 


You’ve gotten this far, the two of you are at a social gathering, a happy hour, or something like that, it’s time to go in for the kill.  As always, you have to rely on your basic human intuition here.  Does this person have more than a passing interest in you?  Is there mutual communication on a regular basis?  If you feel confident that this is the case, then move forward.  If not, let’s keep the friend zone in play for a while longer until you’re absolutely sure. 


Ok, ok, you have a decent idea that this person is interested in you.  Let’s proceed.  If you’re at a happy hour, don’t wait until the end of the night when you’ve both had too much to drink and won’t necessarily remember the details of the conversation.  The middle of the night is the perfect time.  Simply ask him or her whether they would like to go on a date some time.  You can even pre-qualify it with something like, “Hey, I know this might come off a little forward, and don’t feel obligated in any way, but….” 


The key is to gather the courage to ask.  This is a life skill that will take you far.  The worst that can happen is they say no.  You did it the right way, and everything will be find on Monday morning.  Either way, you will feel great about the fact that you asked the question.