Hey Harlan,

I've been harboring a crush on a good friend for four years. We first met in a professional capacity. We went out on a couple of dates, but it quickly became clear that she wasn't romantically interested. We continued to have a professional relationship, and have formed a lasting friendship. We never run short of things to talk about, and spending time together is always effortless. At the moment, though, we live in cities 500 miles apart and are going about our lives independently. I still think about the "what-ifs" occasionally. My question for you is, Would it be appropriate to express my true feelings, and if so, how? Or is it better to let sleeping dogs lie and move on?

Pining

 

Dear Pining,

Sleeping dogs eventually wake up. And when they do, the butt they smelled four years earlier can smell very different (yes, I definitely carried the "sleeping dog" metaphor too far). Maybe she's secretly pining for you, but thinks you're not interested. Maybe the first time around was about her need to focus on a job, not a man. I'm a big fan of the occasional check-in every few years (assuming it won't get you fired). This means giving her another shot at being with the best man (or woman) on the market - YOU. Bring it up casually. Give her permission to not share your feelings. You already know you can still be friends after getting rejected, so there isn't much at stake. If she's not interested, be grateful for her friendship. Then try again in 2015.