LET’S just say there is a really smart, cute girl whom I really like who works in my building. I’ve wanted to ask her out for a long time, several years in fact. Said girl does not work in my department, or on my floor. Also, our jobs are not related at all, and we have no dealings with each other in the course of normal business.
The only time I actually see or interact with her is when we wind up on the elevator together, or arrive or leave work at the same time. The limited interaction is a double-edged sword. On the one hand, it means any potential relationship shouldn’t interfere with work dynamics. On the other hand, it means we barely know each other, and I have no idea if she is even remotely interested.
I don’t want to seem weird or creepy by just showing up at her desk one day to ask her out, but I also don’t know if I have any other choice. I’ve tried to let the opportunity to socialize come naturally, to no avail.
How should I approach this girl at work? Should I even do so?
Jim

Jim,
Sometimes we have to ask to find out what we want to know. How much does that house cost? How do you make oatmeal cookies? Can I have that package delivered to my workplace?
Though we don’t always hear the answer we want, it isn’t a shot at our self-esteem.
Often, life is not try and succeed, try and succeed. Often, life is try, try, try, try…success! When we change the model in our head, it becomes easier to accept the results. This is true in the workplace, and it is true in relationships.
You and this girl have a common ground: Where you work. You know each other, at least slightly. Unlike a stranger in a bar approaching her, she knows where to find you. That gives a woman a sense of security.
You don’t know if she is dating anyone, so why not simply say, “If you are not involved with someone or dating someone, I’d like to go out for coffee with you.” The worst she can say is no, or I’m involved. And that’s fair, isn’t it? To both of you.
Wayne & Tamara