I might be rehashing what others have already said to some degree, but here’s my take on it anyway. FWIW, I feel your pain - I’ve been single for entirely too long lately, but I’m fairly comfortable with it. I know I’m on the right path, and I know why I’m single, and I know what it would take to end it if that were my priority.
First, your negative, “dating’s not worth the trouble” attitude will show through whether you explicitly say it or not. It’ll come across in your tone of voice, your body language, and the off-handed remarks you make without even thinking about it. You have to train yourself not to think like that any more. Every time you hear yourself saying these things in your head, correct it. Seriously. This will work over time.
Second, true confidence is when your opinion of yourself is the only one that matters. If other people are pointing and laughing at you but you know in your heart that you did the right thing, so what? Write 'em off as jackasses and let their scorn roll off your back. The world is full of jackasses and there’s no way to avoid dealing with them. Sometimes they even come in large groups and make you feel like an outsider, or like you did something wrong, but with true confidence you can minimize their effect on your emotional state. Evaluate the “rightness” of your actions based on your own beliefs and attitudes and as long as you’re satisfied that you didn’t screw up, t’hell with what other people think.
OK, now that you have those pesky problems of negative thinking and confidence taken care of (heh), you have to meet women. Enough good advice on this has already been given - find some hobbies and interests and pursue them. Take every opportunity to do so with other people as you can. Hell, take every opportunity for social contact that’s presented to you. Talk to people, both men and women, about the things you care about and that interest you. Make friends. If they’re men, you never know when they’ll introduce you to the woman of your dreams. If they’re women, focus on what you have in common and pursue that. Don’t focus on the “will she date me?” side of things. If she’s not interesting enough to be your friend she’s certainly not going to make a decent life partner, is she?
As far as internet dating goes: I tried this for a while. I had anl ad on Yahoo Personals. For the first 2 or 3 months I got no responses. I contacted a few women who seemed interesting (not many - maybe 3-5) and got no responses back at all. I had a couple women e-mail me at random just to basically tell me what a jerk I was because I didn’t want to date women with kids. But I didn’t give up, and eventually women started contacting me. I don’t know why it took as long as it did, but it worked, and when it did, the floodgates opened. I suddenly had more responses than I knew what to do with. I met a few women, I dated a couple of them, and even fell madly in love once. Not one of those relationships ended up working out. So I decided to back off and focus on myself for a while. But I didn’t give up out of frustration, I made a conscious decision to not pursue a relationship. I’m sure I could have had many more dates, though - after all, it was working. I was meeting people, dating, even having sex! But I was a little emotionally burned out after the whole falling-madly-in-love-and-having-it-end-badly thing and just wanted to back off for a while.
So now I’m working on getting in shape and making money. I figure I’ll find the woman of my dreams when I’m both hot and rich. But seriously, I’m focusing on myself and my interests right now. If I’m eventually going to find a woman or two to share my life, I’ve got to have a life worth sharing, right? I’m not avoiding dating - I’d be happy to date someone if they came along and it felt right (single Doper gals, this means you!) - but I’m not actively seeking it out right now either.
To answer your first question last, no, there’s not a day that goes by that I don’t constantly see women I find attractive and would love to meet/date/have sex with. It’s made worse by the fact that I have a very broad definition of what’s physically attractive.