Dear 100 Hour Board,
So I recently returned from serving a mission, and found out that a girl I had once dated believes that she "waited for me." We had gone on a few dates about a year or two before the mission, we kissed, but things fizzled out and I'm not really interested. She however believes that we are going to get married. To make things more awkward she is a close family friend. How can I break things to her in the least painful way possible for her?
Sometimes we get this idea that we have to be super careful and let people down as gently as possible. We try to do this because we're considerate and care about how other people feel (or at least what they think of us), but it can cause problems when it leads us to be indirect in the way we deal with conflict. The truth is, while it may be more painful, uncomfortable, or even awkward now, being as direct as possible will definitely be less painful in the long run for everyone involved. The fact that she's a family friend makes it even more important that you be direct about your feelings, because it would be especially rude to try to make her disappear from your life forever. By being direct, you can make sure both parties are completely clear on how the other feels, there's some nice solid closure, and you can each move on with your respective lives. Trust me, it's better that way.
Shortly before I returned from my mission there was a girl who told people her fiance was to return. The problem was that she was referring to me and I had never before heard of this. Actually, I had sent her just one letter, not flirtatious in the least. I had also once gone with her to a high school dance. Just a dance, and nothing more.
My family actually obfuscated the day of my return to prevent her from showing up at the airport (which unfortunately meant two of my close guy friends showed up a day early and waited and waited and waited to no avail). When I returned and incredulously learned of my engagement, I avoided this girl for like three weeks, but eventually decided to meet up and told her rather cryptically/ indirectly that we weren't engaged, dating, or anything. While I was vague because I didn't want to hurt her feelings (but neither had I ever heard of the "engagement" from her) the general idea of us not being a thing somehow made it through my social clumsiness and while it made her cry possibly after I left, she appeared to be okay about it. We still talk occasionally, which is about as much interaction as I want.
Were I to go back in time, I would do as The Entomophagist says and just be direct. I would be direct with what I had heard, if she viewed it that way, and then tell her tactfully but clearly how I felt. It's more uncomfortable at the moment but is better long-term.
Isn't it interesting how we can vividly imagine our relationships with others to be something they're not? This idea has freaked me out more than once as I have tried to assess if someone I am interested in has interest in me.
--Ardilla Feroz, from Şanlıurfa, Turkey...a place swarming with pigeons