Dear Prudence,
I’m very new to adult dating and have never had a relationship with someone I met through work. I’ve developed a low-key crush on a work acquaintance, “Brad.” We work in different areas and only intersect occasionally, but Brad is close with one of my work besties, “Scott,” and I know he’s single. We have nice chemistry with each other and I don’t think he’d be mad if I asked him out. But I’ve never made a move, simply because our work has stringent policies against employee relationships. Plus, Brad is highly introverted and shy, so I’d have to make the first move if I want anything to happen.
I just landed a new job and handed in my two weeks notice. Coincidentally, Brad is going in for a medical procedure and won’t be back at work until after I’m gone. I really want to shoot my shot after Brad gets back on his feet from the surgery, but I’m afraid it’s going to come off as weird or creepy. Brad isn’t a social media person, and because we won’t be interacting for a while, I’m afraid it will seem like I’ve been dwelling on him in a weird way. I can easily reach out to him through Scott, but is that appropriate in this kind of situation? I don’t want to put him in an awkward position either. But I really don’t want to miss this opportunity, especially because we won’t be working together or seeing each other otherwise.
—Inexperienced and Interested