January 8th, 2009 
Dear Miss A,
I have a friend and coworker who I absolutely think the world of, and I am pretty sure that I have fallen in love with her. Unfortunately, I am completely paralyzed with fear as to what to do next. I am completely terrified that telling her how I really feel about her will bring irreparable harm to the friendship. But I’m just as scared of not telling her on the chance that she might have similar feelings. At the same time, her not knowing how I feel really her isn’t fair to her either.
Which course of action is most responsible, and how should I broach the subject with her?
Sincerely,
Very, Very Vexed
Dear Very, Very Vexed,
Congratulations! I’m so happy to hear you’ve fallen in love. This is a good thing. You hear so much about men who want casual sex and make booty calls, that it’s so refreshing and inspiring to hear about a man falling in love! (Romance isn’t dead, Ladies!)
The first thing I think you should do is consult your Employee Handbook at work, and see if your company has a policy against inter-office dating. In most cases it’s fine unless she is your subordinate or superior. I would normally warn that you should make sure you’re really into her before getting involved, because the fun of a brief fling wouldn’t be worth the drama involved. Since you think you’re in love, then that’s not a concern. I’m sure you realize that you should keep everything professional in the office, and as distracted as you may be especially at the height of a new relationship, you really do need to focus on work during the day. So do all you can to compartmentalize and not think about her.
Now that the work stuff is covered, how should you go about telling her. I’m assuming that you all must spend time together outside of the office, since you mention your friendship. You probably don’t spend that much time one-on-one, so I think you should ask her to do something alone with you. Not super date-y like a fancy dinner, but definitely something so that this will seem different from your usual pattern of spending time together. Gauge her reaction. Let her see you in a different setting so she can imagine you as a date rather than as guy friend. See how she responds. If everything goes well, proceed like you would on a regular first date.
I don’t think you just lay all your cards on the table and tell her you’re madly in love with her. Just take it date by date, if she is receptive to your advances, and share the fact that you love her after you feel sure she loves you as well. In time, you can share the fact that you fell in love with her before you even dated, and I know she’ll love knowing that.
Good luck! Let me know how it goes. I’m sure my readers would love an update from you.
- Miss A
Andrea Rodgers is a Dating & Relationship Expert for HealthCentral’s Sexual Health Connection. Email questions to missa@askmissa.com.
