To Date or Not to Date

So, I joined a dating website.... against my better judgement. I was convinced by some inadvertent advice from one of my favorite gays. The site is your typical, "indie meets indie" dating site. Lots of hipster, artsy types.
The whole idea freaks me out, to be honest. I know that lots of people find someone through online dating, but I can't really believe I will be one of those people. It goes against my very nature.
The site has introduced me to many types of men... the "let's cyber" guys, the "i want a wife, NOW" guys, the "single dad's looking for mom's" guys... and a random assortment of others.
Some have shown interest, and though I am interested in some, I find it absolutely crippling to reciprocate. How can I open myself up to online dating? Is it possible to be at once strong, guarded and vulnerable?
The question I keep asking myself is, "Am I at the point where I am convinced I won't meet someone "organically"? (p.s. I know I am abusing the "" in this entry)


What I've come to, is that I need to take a leap. Clearly, I am not going to meet anyone in my day to day. I need to open myself up. That said, I can't just let go of my ingrained skepticism, so I'll be choosing VERY carefully.

chugga chugga choo choo

We're in full autumnal swing! Last year around this time, we had just moved to Oregon and Orion and I were just figuring out our life here. This year, we're celebrating having figured some of that out. We know the best pumpkin patches and the most fun apple orchards, we know where to find the yummiest goodies, and we're taking our pick of the most exciting concerts for kids. This is a good feeling! We're chugging right along.
Orion is almost out of his terrible two's which means that my life isn't quite as stressful, which is great. He's asserting himself, and testing boundaries, but usually we're able to resolve any issue with a calm discussion and he ends up making the right choices most of the time.
Every day, I notice little things that remind me that he is NOT a baby anymore. (most often, this is him actually saying, "I'm not a baby anymore Mommy!") I'm at once thrilled to see his growth and development (it is SO exciting to watch!!) and also a little sad that my baby won't be little forever.
This year, he picked out his Halloween costume (He's going as Thomas the Tank Engine), he has a friend to go trick or treating with, and he is very excited to trick or treat. Last year, we had a great time trick or treating with the Portland Single Parents Group, but Orion really had no idea what was going on.
The challenge now is how to entertain this developing, inquisitive and VERY energetic toddler during a long wet winter spent indoors.
I've made some mental notes of places with indoor play spaces, kids activities and I am hoping there will be some dryish days when we can go hiking, since that is a new favorite past time for the both of us.
I'm exhausted just thinking about all that!
Chugga Chugga...

SINGLE mom

Never has the title "single mom" felt more real and more tangible than it does now. Most of the time, I'm thrilled with my life. I have tons of fun with my son, we do lots of great things. This weekend, I took him fishing! Me! Fishing. Crazy. What's more is that I liked it. I could go fishing all the time. I am feeling like I'm doing a decent job of being mommy and daddy. (so much so that Orion has been calling me "daddy" almost as much as mommy lately).
Even though I love our life, and our time together, I'm feeling lonely. I don't know how to "get out there" or date or any of that. It's been a long time, and I've been focusing so hard on being a good mom, and doing everything for Orion. I just don't know how to do anything for myself.
How does a single professional mom find time to find someone? How can I be available, when I'm not? I'm emotionally ready, but the logistics of dating are really intimidating. Babysitters, time away from my son, fitting dates in to my crazy work schedule... all are obstacles.
Other people do it! Maybe that means I'm doing something wrong? I just don't know any more.