Hypothetical Dating For Beginners: Why My Descent Into Lonely Depression Was The Best Thing That Ever Happened To Me

I'm going to tell you about one of the worst emotional periods of my life, and why I thank God every day that it happened.

The loneliest time in my entire life was my Sophomore year in college. Some time in the middle of my Freshman year, I'd fallen for a girl. We were good friends -- best friends, even. Had many of the same interests. Loved spending time together. She was as quirky and uncertain as I was. We went to concerts. We walked the streets of Ann Arbor with no goals in mind other than enjoying one another's company.

For her birthday, she said she wanted me to write her something, so I wrote her a letter: a deep and moving piece of sophomoric prose detailing everything about her that was amazing. She called me that night to say she'd been moved to tears.

But always, always, there were other guys in the picture. She'd end it with one boyfriend just to pick up with another. She'd call me crying and asking why she couldn't just find one good guy.

Early in my Sophomore year, after another night of lamenting to a close friend that we she and I never seemed to click on a romantic level, this friend, a photographer, got her to agree to a photo shoot. During the shoot, he asked her straight out: what, exactly, are you looking for in a boyfriend? I can't remember everything she said, but my friend responded, when she was finished, "you DO know who that pretty much exactly sounds like, right?"

Her: "Don't say Randy."

He told me this, I believe, in order to give me hope. It was his way of telling me she really did have deeper feelings for me, but didn't know it yet.

What I heard was, she wanted everything I was... but not me.

What followed was months of soul-crushing loneliness. I shouldn't have been lonely. I had friends -- good ones! I was constantly busy between the college radio station, classes, the student newspaper, and my job in Dining Services. But I couldn't shake it. I was depressed. I was so lonely, I could actually feel it, like an ice-cold, iron hand wrapped around my heart. I wanted nothing more than for the loneliness to stop. I even considered quitting school. It was... awful. I remember at one particularly low point even reaching out to an ex-girlfriend. I just wanted to talk to somebody who'd loved me once.

I did try dating during that time. Once. She was a Freshman Art student. We had mutual friends, and she seemed interesting enough during our limited interactions. Again, my photographer friend took point in true Wing Man style, setting up a photo shoot in which she and I just happened to be the perfect subjects. We had a great time, laughing and enjoying ourselves and at the end, when I asked her out for a cup of coffee, she said yes.

As broke artsy college student dates go, it wasn't bad. We enjoyed the coffee and the company. We talked and laughed and found ourselves completely and overwhelmingly... uninterested in one another. I asked her to tell me about herself, but my mind wandered a bit as she revealed her disdain for the '60s and '70s (I grew up with that music and was -- am -- a die-hard, unapologetic Dylan fan), and I barely heard her say, "and I really hate guys who say 'dig' instead of 'get' or 'like.'

I nodded. "I can dig it," I said.

After that night, we hardly saw each other again, and greeted each other on our small campus with a friendly nod as we passed. It wasn't that we decided we hated one another. She just wasn't looking for another friend, and neither was I.

In the Spring of that year, my friend Melanie returned from a trip overseas. We knew each other, mostly through work and a class or two (I was a Business Major in my Freshman year), and had developed a friendship during my Freshman year. She knew I was someone she could talk to, and I'd always enjoyed her company.

 After she got back, we spent the work days joking around with another friend, the three of us surviving the hot drudgery of the Dining Commons with humor and sarcasm. She and I got to know each other better and, after she became the student lead for banquets and catering, I found myself volunteering for these events as often as possible. Sure, as a poor college boy, the extra money was an enticement, but really, I just found I enjoyed working with her.

I think I had developed something of a crush at that point. I didn't think much of it at the time, but my loneliness had departed as we spent time together. The depression was gone. I was, in point of fact, happy.

Eventually, we began spending off-work hours together as well. I'd stop by even when I wasn't working in the kitchen, just to say hi. She'd pop in to the college radio station while I was working to keep me from being bored during my shifts. Or call randomly to request a song I hated just because it made us both laugh.

That Summer, we both stayed on campus. We worked together and actually enjoyed it. When we both had time, we'd find ways to spend time together, walking around the tiny municipality of Spring Arbor, hitting the coffee shop or ice cream place. Her brother told her we were dating, and we laughed it off.

But by then, I was already smitten. The more we'd talked, the more I'd gotten to know her, the more my little crush deepened and turned, becoming something much more serious. How could it not? She was beautiful -- former head cheerleader beautiful. She was smart. Competent. Funny. Way, way, way out of my league. She still is.

By the time she was preparing to head home for a few weeks' vacation, I was in love with her. Completely. I didn't know it yet, until she mentioned someone from home had written and that she was considering seeing him during her stay. It was at that point the lessons I'd learned started coming back to me. I realized I couldn't lose any more time. I couldn't risk her going home to New York and seeing this guy, whoever he was, and coming back to school with a new boyfriend. (I didn't know it at the time, but that scenario had never crossed her mind. I'm glad I didn't know.)

I asked her if, "hypothetically," I were to ask her out, what would she say? She said she'd want to know where we were going, and I said dinner and a movie. "You know. Date stuff."

After we failed to talk about it again, I realized I had to grow a pair and let her know I really wasn't speaking hypothetically at all, but actually wanted to ask her out. On a real date. She had to think about it. We were such good friends. It was sounding awfully familiar.

During one of our many non-date excursions, conversation became stilted. Awkward in ways it never had been before. Indeed, our comfort talking to one another was one of the things we'd enjoyed most. It was getting weird. So, because she's intelligent and outspoken, she asked me. "Do we need to talk about something... or is there nothing to talk about?"

We talked. We talked for a long, long time. We talked so long, we ended up going to breakfast at Denny's and then going back to her apartment to talk more. There were no resolutions when we were done talking. She knew where I stood. I knew she had feelings for me, too... but that she was afraid of losing another friendship. It's a valid fear, and she knew where she was coming from in this case. It's not as though it hadn't happened before.

But I'd come from the other side. I'd already sacrificed my heart once on the altar of friendship, and that friendship had died along with it. When it was time for me to go, I stood at the door, my hand hovering over the knob.

"Something wrong?" she asked, a hint of amusement lighting her eyes.

There was. I never fully told her what was running through my mind in those moments, but it was the lessons I'd learned with my former friend. It was the realization that I couldn't just let it go without trying. It was knowing the way I felt about her was far beyond anything I'd ever felt for anyone, ever, It was a truth that, just maybe, hadn't been true in the previous situation: that we -- our lives, our futures, and our happiness -- were worth the risk.

So awkwardly -- as anything done by a shy, nerdy college student must be -- I told her I wasn't sure why, exactly, but I really needed to kiss her.

She responded with the single best piece of relationship advice I'd ever gotten: "Don't analyze it."

We were engaged a few months later; married a year after that. It's been 17 years, we have four kids, and every day I thank God I had my heart broken by a friend. Because, without it, I not only wouldn't have found something even better with Melanie, but I wouldn't have been scared enough of a repeat to do something about it.