I like him, but he is way too shy...

Illustration/Uday Mohite

There is a guy in my building who keeps smiling at me and tries to make conversation whenever he can. He's sweet and I have known him and his family for years. I know he likes me because it's very obvious by now, but he is horrible at communicating and won't be able to manage with me because I am more outgoing and talkative than he will ever be. I think I like him too and would like to consider the idea of going on a few dates with him because I know he would agree instantly if I asked. He can't even work up the courage to ask me out though, which is why I am so hesitant to take this step. If it ends up being horrible, it will only be very awkward for everyone involved because we live in the same place. What should I do?
On the one hand, you want to get to know him, which is possible if you just ask him out. On the other, you presume it will be horrible and may lead to awkwardness. You can't have it both ways. If you want to see what he's like, there is no shortcut, and you will have to spend some time with him. His awkwardness only means you will have to do more to draw him out, because an inability to communicate fluently is not a flaw. It can be learned. Awkwardness can be mitigated by drawing boundaries and being open about what you think can happen. Being upfront about not being sure is fine, because two adults can go on a date, find out that they are not compatible, and still be friends. This simply doesn't have to be a problem unless you both want it to be. I suggest you think about what you really want though, before taking any step in either direction. He lives in your building, so you have time, and can always indulge in more small talk until he is more comfortable around you.

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