It has always been easy for me to get a date, but I am extremely picky about women. So I decided to meet women over the Internet, using the single's ads. Now, you can write this off as goofy and geeky all you want, but I met my wife this way.
There are A LOT of losers on the Internet who place single's ads. But you can sift and filter them. I met seven women this way, and none of them were loser geeks who couldn't otherwise get a date. They were just picky like me, and tired of all the dating bullshit. The seven women I met this way were all above average compared with the women I met the "normal" way.
One of the best things about Internet dating is that you can put all your weird crap on the table before you even meet the person. Ben, you can show women your Web site before they even meet you. If they like it, they will be more likely to like YOU. And if they don't like it, it's better to know now before wasting your time on a pointless date that goes nowhere.
I am the last person who should give you advice. The rock that I've been living under has gotten quite comfortable.
My point is that you're not the only one who hasn't gone out in a while. Whether that's consolation or just makes me look like a loser, I'm not sure. ;)
In my experience though, being honest from the start has always been a plus. If a woman can't accept who you are and/or what you do - then she certainly isn't worth pursuing.
My suggestion? Just mention that you're a writer, you write for the paper, you hope one day to do editorials, you have a moderately popular webjournal you keep for humor and personal pieces. Casually mention, "yeah, it's benkepple.com, check it out some time if you like." Then, late it go and do not talk about her on it again until you're sure she's looked at it. ;-)
She's dating a journalist and a writer. That's all she needs to know. ;-)
Drink more whiskey, and it will come naturally. Sober is no state to be in.