Need you to "weigh" in...(terrible pun, I know)

I'm learning to be brave.  I've had to close offices and layoff hundreds of people.  I've had to fire someone for stalking/inappropriate behavior/porn addictions (and worse).  I've had 2 major surgeries and 2 ER visits in the last 4 months.  I live alone, with the kind of cat that would not only allow a burglar to enter and take all my stuff, but would probably trip the police on their way in to rescue me.  I've sung karaoke.  Hell, I've even eaten trans-fats.

So I'm pretty brave, right?

Thing is, I don't feel brave.  When I've had to do the hard stuff, it's because I've HAD to, not from any sense of bravery.  That's why I chose the weight loss surgery--weight loss is hard, and unless I was forced to eat more healthy (and a whole lot less food in general), I didn't think I could do it.

So today, I'm thinking of things that scare me.  Here's my list:

1. Dating.  By this I mean going and putting up an online profile at Match.com or doing e-harmony.  This is the scariest thing I can think of, which means I either am not living my life right or I am very pathetic.
2. Working out.  Actually going to a place of fitness and doing physical things.  Right now all I can do is walk, but come June 21st my physical restrictions are lifted and I'm supposed to start lifting weights and doing things.  What if I wear the wrong shoes, people?
3. Riding a bike.  When I was little, I loved my bike.  Now, all I can think of is how I must look with both butt cheeks hanging off the seat, and the time I chipped my front tooth because I lost my balance and fell off the bike.  Doesn't sound scary, but without the cap I have a "Dumb and Dumber"-style chip out of my front tooth.  And yes, I lost that cap while on an actual date once (refer back to fear #1)
4. Trying out for choir.  Yea, I sing.  But I don't like doing it in front of actual people, let alone having to audition.
5. Clothes shopping.  Maybe I'll like it when I'm thin enough that clothes fit and look good.
6. Going to the Geneen Roth conference in Seattle in October.  She is the author of "When Food is Love" and "Women, Food, and God" and it would be a great experience.  My parents live not too far away and I could get away for a long weekend with free room and board.  But it scares me to do this and not know anyone and confront my food issues so directly.

Here's where you weigh in.  Comment on this post telling me what it is that scares you, and what on my list of scary things you think I should try first.  I hope someday that my hand will be forced and I'll have to do each and every one of those things, but today I feel like throwing caution to the wind and letting you decide where I start.  Unless you make a bad decision, that is.

Feel free to weigh in whether or not you are a regular reader.  The more, the merrier.  I'll give you until this weekend...