About 2 years ago I had a room available in my home and put an ad on Craigslist. A girl reached out to me (she lived in Portland, OR, I live in Boise, ID), and after a few phone calls, she packed up her things and ended up moving in to my spare room. We've become great friends over the 2 years, and have both helped each other get through a lot of different things.

We have both dated other people while living together, and I have never made any attempt to take things past a friends/business relationship because I didn't want to make things awkward or jeopardize our friendship. I have always been attracted to her, and I think she has been attracted to me. For the last two years I've watched all my friends pursue her, when I've really wished I could be the one pursuing her. We're both very similar personalities, get along great, and I really could see a great future between us if we ever chose to go down that path.

Here's the kicker... She has decided she is going to move to Hawaii, and has her plane ticket already. She's booked to leave December 3rd. The thought of not having her in my life legitimately scares me, and I have been pretty sad off and on thinking that this wonderful woman that I get along so well with is leaving, and I may or may not see her again. She has nothing lined up in Hawaii (work wise) and is going just to go, and see what happens.

Should I tell her how I feel? If I do, how should I approach it to not make it awkward if it turns out she doesn't feel the same way since she'll be living here another month or so? Maybe it's the romantic in me, but I'm hoping that if the feelings mutual she'll stay, and we could actually try to go forward as a team. It's kind of a now or never situation. I honestly wonder if our paths crossed for a reason, and I don't want to look back and wonder what could have been.

Thoughts, suggestions, advice? Thanks so much!

You'll never know until you explain how you feel. She may be just waiting to hear you tell her.

Thanks Ma, I realize that. Hoping for some insight as to how to approach it in general and how to approach it to not make things awkward if she doesn't feel the same way.

I would tell her how you feel. Remember you decided not to go back friendship, so that is perhaps what she saw. So, she may be moving to get a new start, since nothing worked with you.

I would say, if she goes, next time, if you have feelings, act on them and tell people how you feel.

No solution is ever perfect, and dealing with the awkward, or taking a risk of being rejected comes with the territory. You just never know how things will unfold. My advice is hope for the best, but plan for the worst.

Definitely tell her how you feel. It's better to try and fail than to fail because you never tried. Who knows, she might share those feelings and change her mind or make the trip to Hawaii a short vacation and then come back.