Is it better to take risks or not?

Wolfy asks: My friend wants to find me a boyfriend. Honestly I didn’t think she could, but she thinks she has found the perfect guy for me. So I made her a deal: if she can get this guy to ask me out, I will go out with him. BIGGEST RISK OF MY LIFE (so far of course). I feel like those 30 long seconds of making the deal totally changed my life. Have you ever gotten the feeling that something bad or something good will happen to you because of something you did or will do? That’s how I feel. I was sitting right next to her when she tried to tell him that “someone” might like him. He now knows is that this person is in our reading class, so all the girls in the class are “suspects.” He also knows her general looks – all hints to me! He will know it is me by the end of next week. There is one choice I am trying to make – should I let it happen or tell him it is me and no matter what say no to going on a date? Fate, life, the future – the three most unknown, bad, fantastic things all at once. Funny uh!

Hi Wolfy –


I absolutely love this! It sounds exciting and risky (in the best sense), and that you’re pushing yourself forward into an area that is far from comfortable for you.


You asked, “Have you ever gotten the feeling that something bad or something good will happen to you because of something you did or will do?” Oh Wolfy, to me that’s called being Alive!


Look at it this way. Handsome is eating a piece of pizza. Now I could just decide I’m not going to get any, and go outside and sniff around to see what’s happened today. Or I could walk up to him and give him the big round eyes and whine and let him know how much I’d like him to share that yummy treat with me. Now if he gets annoyed and says “no,” and tells me to stop begging, I’m going to feel bad – worse than I would by just going outside. But if he says “sure, here,” I’m going to feel loved and cared for… and happy with how good that pizza tastes! So should I take the risk, or just go outside?


Wolfy, my answer is almost always to take the risk, unless it’s truly unsafe. The downside isn’t that bad (it’s not like Handsome would hit me or yell at me), and the upside is so good! So sure, I’ll take it.


But there’s a bigger reason to take it, which is that if I get rejected, at least I’ll know I tried, and because of that, I’ll feel good about myself. I’ll feel true to my wishes, I’ll feel honest. Again, I’ll feel alive.


There was a famous group of philosophers about seventy years ago who developed a whole theory around this concept, called Existentialism. They believed that the only way to give your life meaning was by making choices – or rather, that the meaning of someone’s life was determined by the choices they made (so if they never took risky choices, that defined who they were).


So again, I’m loving the situation you’re in. But there’s something important here that I don’t know: how do you feel about this boy? Your friend is telling him that you like him, but do you?


You see, while I’m all for taking safe risks, they don’t mean much unless you know what you feel about them. I know I want that pizza! But here, is there something for you to gain from going out with him? If you don’t have any interest in him, it might actually be kinder for you to not go out, since he might start to fall in love with that hair and those eyes of yours, and you’d just have to hurt him by rejecting him.


But if you’re interested at all… oh I totally want to see you go for it, Wolfy! Just make sure you’re safe, and that nothing bad can happen. And as long as that’s the case, this is fun. This is excitement.


This is life!




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