Shy Cub

                                                                                 

Hi Lucia,

I'm 25 years old and kind of shy. There is a pretty gal that I work with, who somewhat resembles you...she is 40 years of age.  I am very attracted to her.  Occasionally her and I have small-talk. I wish I had the courage to eventually ask her out.  What should I do?  Kenny

Hi Kenny,

Before asking her out, ask yourself if things would be awkward if you dated and things didn't work out.  No one wants to go to a job where they have to see an ex that they wish they were still dating or vice versa.  If it's not against company policy and you'll be okay with whatever the outcome is, then go for it.

The good news is that she probably already knows you're interested in her. The bad news is that if she hasn't already made the move herself, then it will be up to you.

Read the full answer at The Cougar Club