How to Deal With Relationships in the Workplace/asking co-worker out


Hi Alice,

Here is the situation.  I am 33 years old and not very good at initially asking a girl out.  I am a part time instructor at a graduate school.  There are 12 of us instructors working together.  I am attracted to one of the new instructors (who I also liked when she was a student a few years ago).  She is 25 and broke up about 2 months ago from a relationship that lasted over a year.  Her reason was that she did not think it was developing into something serious/long term.  

We have become fairly good friends, and often banter with each other.  We already hang out with each other in small groups.  Some of our other colleagues have actually been pushing me to ask her out as well.  On a side note, her birthday is at the end of this month.  

My question is if you have any advice, or if it is even a good idea, to ask her out.  I didn't want to make things too awkward between us.  I thought about a birthday dinner, but this may be slightly ambiguous as to the meaning.  My intention is not to make it a "date," but rather spend time alone with her and see if she is interested.  Or do you think it would be better to do something smaller like coffee or lunch.    

Thanks for taking the time to read this,

Hi Nick,

I'm assuming your small group gets together regularly, like weekly.  Assuming that's correct, my suggestion would be that you ask her to join you for coffee or a bite to eat after the next group gathering.  Either before or after the meeting, say to her, "I'm a bit hungry; how about we grab a quick bite to eat after the meeting, my treat."  

Assuming she says yes, use the time together as an opportunity to get to know each other better, what her interests are, what she likes to do, her family, how she is enjoying the new job, etc.  If that initial outing goes well, tell her you had a great time and that you heard she has a birthday coming up.  Ask if she'd like to go to a movie and dinner as a light celebration.  If she already has birthday plans, let her know you'd still like to do a movie and dinner and then negotiate a date for that to happen.

As an instructor, you have good speaking skills and talking in front of others isn't hard for you.  That should give you confidence in talking with this young woman.  You also know that delays often result in missed opportunities, and things don't get done until one takes action.  It is time to make a move to see if this is the girl for you.  The old adage is true:  a journey of 1,000 miles begins with one step.  Take it!

Take care. I wish you well.

Alice J. Bogert  

How to Deal With Relationships in the Workplace

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alice bogert


I can field questions related to employee-employee relationship issues as well as employee-manager relationship issues.


I supervised staff at the county and federal level for over 25 years. I have extensive experience dealing with employee disputes, management employee disagreements, morale issues, managing change, etc. I teach a variety of leadership and conflict resolution classes.

National Association of Retired Federal Employees, Business Women of America.

I have a Masters Degree in Sociology.

Awards and Honors
Three Quality Step Merit Awards for Excellence while employed with the federal government. Numerous awards for training classes I've done.

Past/Present Clients
Private industry, Los Rio Community College District, federal, state and county government

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