I need to tell her how I feel

New Year's Updates tomorrow.

Hi Meredith,

I'm not usually one to write into a blog, though I've been a semi-frequent reader of yours over the years. I'm writing today because there is this great woman, "Kay," I've known since my first day of college. She is drop-dead gorgeous and also has the sort of sparkling personality that catches your attention pretty quickly. Throughout many years of school (we were in a medical program) we became very close friends but never seemed to be single at the same time. One night, when we were briefly single, she even broached the subject of friends with benefits, but I said I didn't like the idea because I don't think I could do FWB without developing feelings for the person eventually (the discussion was in the abstract but it was clear to me where it would have gone).

We graduated and now live a plane trip away from each other. We have stayed in contact and I finally made a trip to visit her a few weeks ago. We had a grand time just talking about life and our hopes and dreams and how we both feel adrift at this point in our life even though we both have the satisfying jobs we want. We are both happy but want something more. We are both truly single, simultaneously, for the first time since we have met and over the course of my trip I started thinking that she may also have feelings for me too. She even suggested that we would share a bed, adding that "nothing sexual would happen." I declined, thinking I wouldn't be able to hold back from trying something, though in hindsight I'm wondering if she was doing it to just try and get me into bed with her without scaring me off. (Side question: How many people sleep with a person they are attracted to without any sexual thoughts going through their head?)

Luckily, it appears that she'll be coming to New England in a few months. I am dying to tell her how I feel. I almost told her several times when I went to visit her but fear of losing her as a friend kept me from doing it.

After reflecting on it for a while, I don't know if I can keep her as a friend knowing how strong my feelings are and how much stronger they became when I went to visit her. Every person I've talked to says I should just tell her. She's even met my parents and they are completely baffled as to why I haven't pursed her openly yet. So my problem is this: Why am I more petrified than a mosquito in amber? The bigger question is that I have no idea how to start the conversation with her. What do I say to start? I feel like if I could just get the first few lines out the right way everything will work out.

– Can't Just Do It, New England

Do it, CJDI. Tell her. Say, "Kay, when I was visiting you, I turned down sleeping in your bed because I have feelings for you and didn't want to tempt myself. I know we're living far away from each other, but I'd like to lean in and kiss you and then see if we can turn this into something awesome."

If I were you, I'd tell her before she gets here -- by phone -- so that she can ponder it all before she's standing right in front of you. Maybe she'll let you down easy before she gets here. Or maybe she'll spend the next few months picking out an awesome pair of pajamas for the trip.

I know it would be more romantic to tell her in person, but you guys have a habit of not being single at the right time. She could get a boyfriend within the next two months. Don't miss your window.

And for the record, the bed sharing thing is suspect (in a good way). It sounds like she had a perfectly nice couch. So yeah, it's very possible that she wanted to see if you were willing to sleep by her side. It's possible she wanted to give you an in for that first kiss.

Put it out there and then tell us what happened. You have every reason to be hopeful and nothing but bottled-up feelings to lose.

Readers? Should he tell her now that she lives far away? Should he tell her in person or before she gets here? How should he say it? Script him and help.

– Meredith