Back in my undergrad days – many, many moons ago – I sang A Capella. (If you’re curious, I’m a 2nd soprano, but I’m pretty solid on alto when necessary.) Anyway, at the time, we did a cover of this one song that I absolutely hated, called “How Do You Tell Someone,” by Cowboy Mouth. I still don’t like it all that much, but lately the refrain has just been swimming around in my head. It’s starting to make a lot more sense.

I’m not entirely sure how I’ve gotten to this spot. It would be nice if something started to make sense to me soon, though. What I’ve been able to work out thus far is:

• Wildly unpopular little kid. I was poor, shabbily dressed, awkward, uncoordinated, nerdy, chubby, and had glasses, and was regularly bullied until high school.
• In high school I grew hips and boobs, and became something like nerd-dom’s high ranking official at Northside High, reigning over quiz bowl teams and academic clubs, and dating a new guy every month or so. I was known for my epic makeout sessions on school field trips – but I was also known for being very devoted to remaining a virgin, so I didn’t get into anything too heavy.
• In college, I got more serious about dating, and eventually I fell head over heels in love – twice in a row. The first one never liked me that much, but led me on. The second one loved me back, but in the end he chose his musical career over me, and dumped me to have more time to play music. He really messed with my head, even though he was probably the only guy I ever dated who sincerely didn’t want to hurt me. He’s a great musician now, so his choices definitely paid off.
• It took me a few years to get over that last relationship, and I was still a complete and utter mess. When I say mess, I mean borderline mental. Imagine any TV show you’ve ever seen where the guy has a psychotic ex girfriend who’s plotting something sinister. That was me, every day. I wasn’t out of my mind all the time, but the right conversation and a few drinks could create utter havoc in my life. I just couldn’t control my emotions.
• Eventually I decided that I wouldn’t fall in love again. It wasn’t worth the pain. For years I thought that the decision was just a joke, but I’m beginning to wonder if it was real.

Then I met The Man. At the time I was dating two men casually, and had to eventually make the decision to drop one. The Man loved me, and was my friend, and for the first time, here was someone putting everything out on the table for me, no games, no lies, just real talk about the future and how to get there. Plus, he was drop dead gorgeous and kept his pantry stocked with clam chowder for me. So of course I chose him. He was a grownup, and I’d never dated one before. That was over seven years ago. Unfortunately, now I see that what I thought was maturity and responsibility is actually just predictability and lack of adventure. I loved him for a long time, and really liked him for a lot longer, but now it’s all wearing a bit thin, and I’m not sure if I’ve got enough emotional duct tape to patch up the holes again.

So how do you tell a guy with effortless four-pack abs, a gorgeous, chiseled jawline, and perfect hair (he’s straight out of J.Crew), who loves to clean the house, cook all the food, wait on you hand and foot and wants nothing more than to have you be the mother of his children and live in a Victorian house by the ocean that you just aren’t that into him? Especially when in every sense of the word, he has it going on, and you, well, just don’t?

My head is spinning. It’s not like he doesn’t fit quite a few of my “wants” for a potential mate. It’s not like he’s doing anything wrong. He does everything so right that I even feel shittier about this now than a month ago when I first started making serious plans to leave. He’s ridiculously thoughtful, and always has been. Tonight when he was leaving, he even stopped to tilt the TV on its stand so it was facing me properly where I was sitting on the couch. He sends me love notes. He bought me Magic Mike yesterday and hid it in my purse to surprise me. He even buys me toys. The good kind. But none of it is enough. None of it makes my heart stir. It just makes me feel guilty for not being able to flip that switch and respond to him with the passion he deserves.

A friend of mine told me the other night that I’ve given myself this glass ceiling, and it’s my job to break through. I know in my heart that what he’s saying is right. And I know that settling is a classic mistake, and it will make me miserable for the rest of my life. But I’m not settling because it makes me feel secure. I’m settling because I don’t want to break a heart. Every time I’ve told The Man that I feel like things are over, he asks me for a list of things to improve, and then improves them. He’s seriously the most kick-ass boyfriend a girl could ask for, as long as she never wanted a man she could dance with, and duet with, drink wine with, laugh over cards with, talk about God and feelings and the beauty of the ocean with, or any of the 100 things that make me feel most alive that he will never, ever get.

So how do you tell someone? And then how do you get the hell out of dodge immediately afterwards?