All You Need is Love... and Guts

Recently a former student came to me with that classic problem: a girl. Not that the girl was the trouble, but his feeling for her were. You see, he was firmly entrenched in the "friend zone" (how deeply even he didn't realize until he had given my wife and I some details) and he wanted to get out. To me, the friend zone is a place where guys seem to go far more frequently than girls, the ratio is something like 5:1 in there.
It boiled down to the same issue it does for most of us when we have found ourselves dug in to that deep defensive trench of friendship; do we go over the top, risk it all and go for the glory or do we stay where we are, out of the wind, unable to be hurt but never getting anywhere? Everyone agrees that once you go over the top everything changes, for ill or good you won't know until you've done it.
After a long long long (we're talking two in the morning in suburbia here) talk I gave him the only advice I could give: Go for it.
It is disingenuous to stay in a relationship when the other party is possessed of a totally different idea of it than you. He was scared, afraid that she would stop talking to him, no longer let him snatch up the little snippets of her affection that he gets. In fact, he seems to think that outcome is much more likely than her reciprocating. But it's just not the way to go about it. How do I know? I've been there, more than once.
There I am, fifteen years old and madly in crush with a girl from my old school who I barely ever see anymore. Now a crush at fifteen is a serious business, it effects every aspect of your day and your thoughts. I was talking to her over AOL (remember when Messaging was confined to pay services or IRC?) and the subject of HER latest crush came up. Eventually we work our way around to who it may be that I like, my heart racing the whole time. It comes out, I tell her- or rather type to her, not the smoothest proclamation of love, I'm sure. Chaos ensues. She is shocked, unable to understand, maybe even a little disgusted.
This was my first introduction to the friend zone- she just did not have any idea that I was investing this much time and interest in her for anything but platonic reasons- she was doing the same and there was no interest on her side. Now, the thing is, I knew that. Or, I should say, I was fairly certain of it- but it didn't matter. Even at fifteen I knew that if you don't try you don't get the girl, so I went for it, blindly, badly and selfishly, but I tried.
POST-SCRIPT #1- this girl went on, after about a year of almost no conversation, to become my best friend (platonic, of course) from senior year till the end of college. Not a bad deal, I think.

Now we get to the tough one, the one that really paralleled my student's issue and that I have the most trouble writing about. I was a senior in High School and she was a Sophomore in a different school, we had a few of the same friends and saw each other at events and pizza shops. Eventually we ended up working together in the same Chinese Take-Out place. She was funny, bizarrely so. She was pretty, in a cute, shyly un-shy way. She was a good friend. And one night I had a dream, an incredibly vivid and non-sexual dream about her. I just couldn't get it out of my head. There were definitely romantic overtones in the dream (most of it was candle-lit) but it was the sense of comfort the dream conveyed that convinced me to convince myself that I was madly in love with her.
Her sister took us all out to a movie on her birthday. I gave her some lame gift that showed I had been listening to all her little concerns and issues and I went home. That night, on the phone (see, no Internet- I was getting better!), I told her. Unlike the last time, she didn't recoil in fear or shock, she actually denied that I could feel that way and cried. I went on enumerating the reasons I loved her and pushed and pushed. She needed time, I would give her a day. We worked together the next day and barely spoke of it. On the phone that night she said she was very fond of me and that we could give it a try.
What followed was an odd, occasionally long-distance relationship that probably had more to do with who I am today than most of what I learned in classes at college. It ended one rainy day in February, shortly after my birthday with a letter she handed me and her running off in the rain. After reading the letter in a daze I rode the train confused and saddened with a pain I had never known before.
I won't go on to talk about all my pleadings and attacks to try and win her back- it didn't happen and I grew from it in ways I can't begin to enumerate.

Flash forward to a year later, a new group of friends and a new crush. She was one of the girls my friends and I often went out drinking with and I couldn't stop thinking about her. I talked about her to old friends and strangers, I found her fascinating and funny. Not one to be dissuaded by past failures, I worked up the courage to ask her out. (Face-to-face, no less!) She quite blithely refused, saying I wasn't her type. I insisted that she give me a chance, she just kept refusing. Finally, I convinced her to go on a "not-date" with me, Coffee and a movie, just to see if maybe she had the wrong idea of who I was or what type she really wanted. What followed was a trio of "not-dates" that all ended the same way: with me asking her if she had changed her mind and her telling me that she had had a great time, but was just not interested in me "that way". We parted as friends and a few months later she was gone, transferred to a college in Canada.
POST-SCRIPT #2- a year later when she came to visit friends in NY she insisted on seeing me, to see how I was and talk about old times. Apparently, I was important to her as a friend and she missed me. We were both able to laugh about my persistence and agree that her perseverance was correct.

So what's the point of all this? That I constantly tried to get myself out of the friend zone and failed time after time? My student didn't really see this as encouragement for him to do what I was saying. I tried to explain that each of these experiences ended in the way they had to and that they had helped form me into the person I was, the person he respected and liked. But more importantly, my attempts had given me the courage and experience to tackle the hardest crush I ever had.
It's the summer after the last girl went to Canada and I am, pompously, sending out little e-mail updates to all my friends about my life (this was the days before blogs and I like to think my one hundred plus e-mails were an early form of that now ubiquitous medium). One of my friends reads one of these e-mails with her friend looking over her shoulder, the girl finds it amusing and interesting, and insists her friend send an e-mail to me to add her to my list. Soon enough we are talking on the Internet for hours at a time and I find myself falling again, HARD. This girl is it, she is the culmination of everything I love about the opposite sex. She shares my interests and has the same sense of humor as me. Undaunted by all my past failures, I take another stab at "getting the girl" I won't go into all the trials and tribulations our relationship had; the friends who didn't want us to be together, her father's strict rules about dating and his distaste for me. Everything seemed to be set against us, but we were an US. I had found someone who felt about me the same way I felt about her and through it all, she stayed by my side. My life changed into something almost unrecognizable and completely unimaginable six months earlier. In the end, it worked out- we got married a year and a half after our first conversation.
POST-SCRIPT #3- Sarah, the mother of my two children, and I are very happy together and my student who came to me for advice likes her and respects her even more than he does me.

As I said, what's the point of all this? Why did I feel the need to unburden myself unto my poor, confused student? Because he needed to know that failure IS an option, that every time you would rather just hunker down and stay out of the fighting you are cheating yourself out of life. Every time you would rather suffer in silence and let the status quo prevail you aren't just missing out on a chance, but on life itself.
Courage is not the act of facing obstacles you can overcome but the action of facing the unknown, going into the fray when you have no idea what is going to happen. Obstacles are so named because they are IN THE WAY, they are something you need to deal with. If you ignore them or try to get around them without facing them you don't just cheat yourself- you, most likely, find yourself right back were you started, having learned nothing.

Feel free to share your own obstacles and defeats that have shaped you as a person below.

Principles: Obstacles, Courage.