Should I tell him how I feel?

Hi Meredith,
I'm a 20something female professional living in Boston. While I've dated around, I'm admittedly a romantic moron in that I've never had a long-term relationship.

A few years ago, I met "Tom" through a friend. Tom and the friend go to grad school together in another state, but I visit often (every other month or so). Tom is one of those genuinely nice/goofy/nerdy guys, and we share a lot of the same interests. About a year ago, I realized that I had romantic feelings for Tom that I am pretty sure are reciprocated. When our friends see us together, they tell me it's clear that he's interested. When I come to visit, he'll go out of his way to meet up with us, and we spend a lot of time talking one-on-one. He laughs at my lame jokes, and I laugh at his. We stay close to each other at parties/bars. He's visited Boston a few times (he has family in the area), and while he was here recently, we went out together alone. He paid, but it was never overtly called a "date."

However, it's never progressed past friends. I know he's not gay, and he's not dating anyone at the moment. He's very shy and a bit of a romantic moron himself, which may be why he hasn't ever seized the moment, but I've given him plenty of signals. I'm usually the one reaching out to him, but he's always very eager to meet up when I'm around. While my friends yell at me to make a move, I'm never sure how to go about it, and it never seems to be the right time. Further complicating the matter, he's finishing grad school this spring, and he's probably going to move far away. I don't want to sign up for a long-distance relationship, but I feel that I need to tell him how I feel.

What should I do? Is it even worth telling him how I feel when he will only move away? If I should tell him, which I'm leaning toward, how do I word it without scaring him? Aghhh! I'm so not good at these things. I've been online dating, and I even dated another guy for a few months (which ended a while ago). However, Tom is always in the back of mind.

– Romantic Moron, Boston

It's been a while since we've heard a good story about Deredith Boldstein.

Let's gather 'round the campfire and I'll tell you another tale.

Once upon a time, in ... let's say ... 1993 ... Deredith fell in love for the first time. She was only a teenager, but she was sure about this boy. She just didn't know how to admit her feelings. She was friends with the young man and he seemed to love her company. She didn't want to ruin it, so she kept quiet for a long time. A very, very, very long time.

Finally, one night, she snapped. After leaving a party at the young man's house, Deredith ran back inside and called out to him, "I have more-than-friend feelings for you!" The young boy looked stunned. Probably because his mom was upstairs. Bewildered, he told her that he didn't know how to respond but that he was happy she disclosed her feelings. Deredith left his house without an answer. The next day, the boy told her that he didn't reciprocate her feelings but that he cared about her very much.

The thing is, even with the rejection, Deredith didn't regret telling the boy how she felt. In fact, she got a strange rush from putting it all out there. She felt powerful. She felt strong. She felt like a sexual being (even thought she had barely hit puberty and had really unfortunate bangs).

The lesson here, I think, is that it always feels good to get it all out there. There's something awesome about saying, like a rock star, "Let's do this thing." And that's pretty much how I think you should say it. "Tom, I have more-than-friend feelings for you. I know that you're leaving and that we've both been slow to talk about this, but I want you to know how I feel. Because I like you."

Get to it. You have nothing to lose but ambiguity. And please, update us soon.

Readers? Thoughts? Got an idea for a speech for the LW? Is it worth disclosing knowing that he's going away? Is there any reason not to disclose? Is there anything to lose? Discuss.

– Meredith