Can I have some advice about my love life?

For most of ages 15–25, I was in relationships. In the last one things went wrong slowly, like the frog in the boiling water. Brian wanted me to spend all my (limited) free time with him. He wanted me to quit my job, move in with him, and work part time while going to college. I wanted to start a career with wine. We kept getting into fights about it, he wouldn’t back down, and that’s when I finally ended it.

Andy was one of our vendors; he knew me when I was just a cashier. I became a buyer/ manager, and after that we worked together often. (I’m 26, he’s 42.)

Andy is… different. He’s rather awkward and nerdy, and his fashion sense is like this.) He’s tried online dating for years; it never works out. He dresses up for renaissance faire, and lost years of his life to World of Warcraft, is what I’m saying. I kind of… suspect… that he might be a virgin.

He also has a goofy sense of humor, and a hidden thoughtful side. Our conversations became ironic banter filled with elaborate running jokes. Sometimes circumstances brought us together outside work. Then we ended up talking for hours, long after everyone else went home.

Once a party lasted until 2 or 3 AM. We talked all night and went down to the river to watch the sun rise. It was one of those meandering conversations about everything- books and music, old family secrets nerdy stuff, our worldviews, and our hopes and dreams. He wants to meet someone smart and interesting and have a family someday. In the morning he gave me a hug and we went home.

My breakup was a year ago, and Andy was assigned to a new sales route. I waited two months, gathered my courage, and asked him out in an e-mail. It took him a month to answer (why???). He said that he believes in me, and thinks I’m going to have an amazing career. But he’s “not ready yet, and maybe I never will be, but I hope not.”

Since then, I’ve stayed single on purpose. I want to work on my life for a while. In a question below I asked about depression; I need to figure out how to be happy. In the last year I’ve made some big strides, like getting in touch with old friends, getting in better shape, improving my finances, and getting a car. For the first time, things are pretty much ok. I’m not struggling financially anymore, and I’m starting to have a fun and active social life.

But I’m still- heartbroken? I might stay single for a very long time.

I’m afraid of dating again. What if it’s another Brian? He slowly took over my life, and the more that happened, the less I was attracted to him. He made me feel like I “owed” him sex because we were in a relationship, and I consented to sex that I didn’t want, many times. It’s amazing that it took me so long to leave.

In a lifetime you meet a handful of kindred spirits, and I think Andy was one. People say I’m a space cadet, or I’m out in the ether, but I’m just thinking. For once, someone was out there with me. If I date again, I want that same kind of connection, and it’s so rare.

For now, I’ll just keep on keeping on, I guess. It seems like it will be a while before I really feel better and my life is in a better place. Honestly I thought a year would be enough time, but it’s like I’m just getting started. Have you ever purposely been single for a long time? Am I on the right track?