In putting ourselves out there to meet others we run the risk of rejection. I'm an out-of-work actor . . . I know all about rejection! It's not easy. I'm also very shy &, were it not for my 3 best friends - especially my roomie Noah, I don't think I'd get out very much. I spend very little personal time online but I read, I watch films, I work out & play sports, I play guitar. But I have buddies who I can rely on. It would be very difficult without them. Most of the girls I've ever dated I've met through them. Except the girl I'm seeing now, who I met almost by accident, a fluke really. You never know when you're going to meet someone. But you won't meet anyone if you don't get out there!
Moresecode, do you have any hobbies? Over a year ago, I got into photography. Real photography where I develop my own black & white film in my kitchen sink. Look into a hobby that would get you out among other people. Take a class in something that interests you at your local junior college (or whatever they have up there in Canada), a class that would get you involved with other people directly. How about ballrooom or swing dancing? Or . . . I kid you not, square dancing? I know a guy who met a really lovely girl in such a class! And it's fun - it's exercise! And I don't care if the women there are not girls you'd seriously think about seeing. Your confidence will rise just learning & interacting with people! My years as an actor taught me this; if you do something you've never done before & keep at it, you'll get better at it & have this amazing sense of accomplishment. That's how I feel about my photography! It makes me feel amazing to develop some crappy pictures I took on a $25 plastic Holga & post them to my Flikr page or give to others for birthday or Christmas gifts. It's a wonderful self-esteem building thing.
I also agree with the suggestion to begin a regular exercise program. That means cardio at least 3 times a week & some sort of weight lifting. Here in CA, we've had some horrible fires recently & I was unable to go on my jogs for almost a month, the smoke was so bad. My body missed the effort. In case you don't know, our bodies actually produce feel-good chemicals, like endorphins, when we work out! Seriously, a routine exercise program would help you immensely! Your goal might not be to look like a bodybuilder but, like mine is, to be fit & healthy. That's a good goal. If you currently don't exercise, start by taking a walk in your neighborhood (if it's safe). You begin to feel better about yourself within a week or so. I promise.
If talking would help, PM me or any of the others here who've offered (if I know the folks on this site, they mean it from the heart - most of them). Therapy might help in your situation, it's helped with some friends of mine but I'm not big on it. If you're religious, see your priest or pastor for guidance. Try reading the Bible, if you don't - start with the New Testament. Even if you're not a believer, I guarantee you will find something you don't expect there that will help you.
Also, & I think this is VERY important: Project what you want to get back. It's been referred to as the Golden Rule: Do unto others as you would have them do to you. Smile at people. Wish them a good day. When others say "thank you" to you, say "you're welcome" back to them & . . . here's the kicker . . . mean it! I firmly believe that it's all about love, folks. Show others - all others, even those you find it hard to get along with - love at all times. That love will come back to you. Paul wrote it: "In the end, the love you make is equal to the love you take." There is so much beauty in our world. It's so much fun to add to that beauty by being kind & loving. It's much to easy to be nasty & bitchy, frankly. That way lies the darkside, padawan! I agree with the other poster that getting out to volunteer at a soup kitchen or other such thing would help you, too. Do something totally selfless &, in doing so, you'll find more of yourself! The more I lose who I am in doing things for others, the more I feel I become who I really am. But that's just me. I like doing that stuff.
For me, it's all about discipline. Keeping yourself busy doing thing that interest you & keep your mind & body engaged in a positive direction. I was depressed for about 2 years & it took a toll on my body. I know what it's like. Do NOT give up. Always make the concerted effort to be positive, to make the positive choice rather than the choice that will support poor self-esteem.
Take if from my experience - & this may sound like new-agey platitude bullshit but it's very true: You are loved. Even if you don't realize it yet!
Sorry, pal, I went on too long. I hope this helps. You are not alone.