Should I Tell Him How I Feel?

Wednesday | February 23, 2011

Love Letters Dating

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 mutually 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.

– 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 … 1994 … 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 long, long, 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 think I’m in love with you!” The young boy looked stunned. Probably because his mom was upstairs. Bewildered, he told her he didn’t know how to respond but that he was happy she told him. Deredith left his house without an answer. The next day, the boy told her he didn’t quite reciprocate those romantic feelings.

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 out there. There’s something awesome about saying, like a rock star, “Let’s do this thing.” The high you’ll get from your own bravery will combat any bad news you have to withstand. And it’s quite possible you’ll hear good news. After all, you and Tom are much older than Deredith and her unrequited crush (who wound up marrying a flautist and moving to Connecticut).

Get to it. Disclose, just like they do in the movies. You have nothing to lose but ambiguity. And please, update us soon.

– Meredith

Dating