Don't hold back.

"Pessimism is my insurance policy," I said, "If I don't expect it to go well then I'll be pleasantly surprised if it does, and I'll be prepared if it goes how I predicted."
Ladies and gentlemen, this is the biggest lie I've ever told myself. And I've spent years telling it.  
Preparation is great. If it's raining, I wear my rain coat. If the paper is due on Wednesday, I have a rough draft by at least Monday. If the choir concert is next week, I'm drinking tea and staying hydrated every day. These are all things of certainty. Real events and tangible deadlines. How can we handle those times when the outcome is distant and clouded? What happens when the variables are human beings, who are so changeable? Obviously I thought I had the answer - Expect the worst from everyone. Protect yourself carefully by putting up walls of logic and apathy. 
This is not the way we were meant to live. Which is why it never works.
Unless the situation in question is something that honestly has little effect on me, I cannot help but get emotionally involved and desire certain outcomes. For a long time I was ashamed of this, but I've realised that humans were created to be passionate beings. God has given us minds that are capable of well-placed confidence (faith), forward thinking (hope), and attachment (love). His plan for us is the only insurance we need. James 5:13 says, "Is any one of you in trouble? He should pray. Is anyone happy? Let him sing songs of praise." It's okay to get caught up in joy! Because when our preparations fall through and trouble comes, we can turn to God and trust that he has everything under control. 
A couple of weeks ago I read an awesome article (found here) that speaks out against the idea of "guarding your heart". It's an idea that has been innocently circulated among young Christians who want to remain pure. Secular culture has also mirrored the sentiment (or lack thereof). It's said that we should be careful about who we love and how we let them know, to keep ourselves from getting hurt and to make sure we have enough love to give to the right person. Is love a limited quantity? The world today makes a huge deal out of saying the words "I love you". Why is it so hard to acknowledge how important someone is to us? Love is both the easiest and the hardest thing to give. It's something we desire, but it also leaves us vulnerable. That's why trust is so important in relationships. A trusting and self-sacrificing love is sometimes hard for non-Christians to understand.
For those in Christian culture, withholding love goes too far when we take God's law of saving sex for marriage and extend it to ban most kinds of physical affection and deep emotional attachment. Some well-meaning mentors would have us believe that if we allow ourselves to love another person completely, then we're distracted from loving God with our whole heart. On the contrary, God opens our hearts, and our love for each other is fulfilled by God and feeds our faith! One of the best places that helps us to understand love is in 1 John 4, (here I quote verse 8 and 11-12) "Whoever does not love does not know God, because God is love...Dear friends, since God so loved us, we also ought to love one another. No one has ever seen God; but if we love one another, God lives in us and his love is made complete in us." 
In the end, no amount of preparation or protection can keep us from being hurt when something important goes awry. Our foundation and happiness lies with Christ, who gave his life to protect us, and still holds us close today. When we have learned to trust in his secure love, we can share that love with the people in our lives. Many times I've noted that relationships with my fellow Christians are deeper and more fulfilling. Perhaps this is because I can show them unrestrained love modeled by Christ, and receive the same in return. 
Our compassion is a continuation of the love we've been given freely, which will never fail us.