I met a charming woman during my work event and I can’t stop thinking about her. We had a brief chat over a drink, but I was too shy to ask for her number or to ask her out. We work in different departments, so normally I don’t get to see her. I found her via employee directory, but I am not sure if contacting her via her work email is the right thing to do. She is confident and successful head of a department and I am just a regular clerk and I am dreading that she will never look at me as at a potential match or even worse, she will tell everybody that I am hitting on her. Shall I just try and forget her?
When it comes to working situations you do have to be careful. I understand where you are coming from as you do not want people in your company talking about your crush on your colleague or even worse – get Human Resources involved. What I would suggest is for you to take your time and find a way to stop by her department every once in a while to say “hello”. The difference here is you’re in a work environment so you will have to pace yourself instead of going after the woman that you want. You want to make sure there is a mutual attraction and you will figure it out as time goes on. For now, pacing yourself will be the best thing to do. A couple of suggestions I think will help you is going to social events the office is having and start talking to her about things at work and then start asking her personal questions, such as what she does for fun, what food she likes, how long she’s lived here and the like. Once this has happened a couple of times and you have built a familiar relationship with her and you see that she is reciprocating or possibly flirting with you, use the opportunity and ask her for lunch. I do think that you have to set the tone for this. So, for example, you both are hanging out at a work-related event. Ask her what her favorite place is to grab lunch. Then reply “Ok, I’ll have to try it out, let me know when you go”. That way you are already planting a seed and you can see if she reciprocates and take it from there.