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I was wondering if you can point me toward a resource on . . . well, dating. Something like a "Dating for Dummies" kind of book or website that has your seal of approval. I got married way too young, and after 14 years with the same person, I was done. We divorced over a year ago, and I just turned 34 on New Year's Day. Although I've worked through a lot of my own issues and think I've become a better person with more confidence in my identity, I am clueless when it comes to dating. It's funny that I have confidence to be able to talk to nearly anyone and cut loose freely (you should see me karaoke sometime), but when I try to ask someone out . . . oh good gawd. So embarrassing. I'm an awkward dork. Help!
—Awkward & Alone
Obviously I'm going to recommend my book, How Not to Date, and advise you to keep reading this column. A stroll through the archives will yield plenty of helpful advice.
The thing you need to remember about asking someone out on a date is that everyone finds it awkward, embarrassing, and slightly mortifying. OK, wait, let's amend that: If you're fantastically handsome, incredibly rich, powerful, and/or famous—or even if you're butt-ugly but possess those last two qualities—you probably have no trouble asking women out because you're used to dodging all the vagina thrown your way on a regular basis. Like George Clooney probably has no problem asking people out. But for the rest of us, it's uncomfortable.
You've already clarified that you have no problem talking to strangers or even doing one of the scariest things in the world next to bungee jumping: karaoke. Isn't asking a pretty young thing out to dinner and possibly maybe getting shot down (but also possibly maybe not) a lot less ridiculous than belting out "Jolene" to a room full of drunks? I'd rather have some dude laugh in my face than be forced to sing "You Give Love a Bad Name" in front of other humans.
As your luck would have it, most of the women who write me complain that men in Seattle are completely passive and never ask a girl out. They seem more inclined to mumble something about "hanging out sometime" to indicate interest and quickly slink away. So the mere act of walking up to a woman and offering a hey-how-ya-doin' pushes you miles ahead of your peer group. Add a little flirty eye contact? A total panty-soaker. Up the ante with a "Hey, wanna get coffee?" Her ankles will be wrapped around her neck. So go get 'em, Tiger. And let me know how it works out.