I’m approaching another Boy At The Window related milestone this week, a not-so-fun twenty years since experiencing an obsession-driven heartbreak. This involved another crush, another young woman out of my league, one which left me scarred for a little more than a year.

She was one of those mid- to late-80s cool Black girls, attractive and popular, yet one of the nicest people I’d known during my middle school and high school days. The things I remember about her most are kind of silly and sensuous. I remember her long legs, her long dark hair, her always wearing skirts in public. I remember her lips and bright white smile most of all. She was all of 5’7″, and seemed to be always there to pick up my spirits. I guess that was why I ended up wanting to date her by the middle of my junior year.

But images of the mind, no matter how powerful and complex, can only begin to capture the reality of the person who could be the object of your affection. So it was with shy and pitiful me our senior year and the summer before college. I tried but I could never figure out a way to ask her out, to tell her that I liked her, to tell her that I was terrified of my own emotions about her and about her learning about my family. After a few weeks of stifled attempts at conversation, I accidentally ended up overhearing a bitter conversation about me between my crush and her sister outside of a mall in White Plains. I wasn’t a man, I certainly wasn’t a Black man, so she kept saying to her sister.

I was devastated. I didn’t have the greatest opinion of myself to begin with. I went into my freshman year of college at the University of Pittsburgh more protective of my heart than I’d ever been. Still, with the help of a female friend that I’d made during the summer, I decided to confront my obsession, leading to a letter that brought me more despair and heartache. She had all but destroyed my image of her as someone who could save me from the horrors of my world, someone who I could pour all of my confidence and aspirations into.

I finished that semester with a C+ average, homesick and not sure about people or my future. I completely distrusted anything any woman had to say about me that semester. Most of all, I distrusted myself. How could I allow this “triflin’ ass” — as one of my friends described her — affect my grades, my life like she had? I took all of that anger and focused it on my classes, and pulled my over GPA back up to a B in the process.

You could say that I learned my lesson. But that would be a lie. I had to go through a summer of unemployment and a week of homelessness my sophomore year at Pitt before I learned one of life’s most important lessons. Trust is a decision that we all have to make, even if it does mean heartbreak, because trust — especially in yourself — allows you to see people as they are and as you would hope they could be. Trust means taking risks with your heart, means being honest with yourself about why you may be terrified to date or for someone to know about your dark past. Trust means that people, even people you may know fairly well, may betray you in some way, but trusting anyway, because it’s the only way to live a great life.

I also learned that much of what I thought I saw in my second crush reminded me a lot of my mother. Especially around definitions of manhood and being a Black male. We were supposed to be bold, even arrogant. We were expected to make the first move, in dating or otherwise. We were supposed to break away from our families but be there for them at the same time, to succeed in the world but never forget where we came from. I realized that my mother and my obsession were both wrong, that they didn’t know me, and had no right to lay their expectations on me. I figured out, for the first time in my life, that having a mind as powerful as mine brought with it the responsibility to tame it, especially when it came to figuring out men and women. I needed to trust my instincts, that a bright smile and wonderful lips didn’t equal a sense of seriousness or integrity or actual kindness. I could still dream of a kiss. I just needed to make sure that the rest of the person in that dream was worth kissing.

Still, I have to thank her, my second infatuation. I wouldn’t have known what not to look for in women or in friends without this experience. I learned as much about what attracted me to my first crush as I did about what kept me from going after my second one. The women I’ve dated and the woman I married all benefitted from my period of mindful obsession. My college education, formal and informal, became that much sweeter once I let go and allowed myself the opportunities that only trust in myself could bring.