I was reading your column and noticed an ad about singles on the same page. It talked about being available, telling your friends you're looking, and using chat lines and advised that I SMILE AT A STRANGER. Well, I'm kinda the older guy in good athletic shape looking for a younger girl in similar shape. I walk Green Lake several times a week trying to make eye contact and to smile at someone I find interesting. I find that hardly anyone looks up and even fewer smile back. I am sure I am not the only one in this position. If there are any such women, they must really want to be alone. Just a simple smile and a "hello" would be a good start.
You know, a handsome fellow named Ted Bundy built quite a career for himself by hooking up with pretty young women in well-trafficked public parks. He'd reel the ladies in by wrapping his arm in a fake cast and asking the first cute girl he saw to help him carry his things to his car. When he got them to his car, he'd offer them a ride. Once inside, they'd eventually notice that there was no interior door handle. Their goose: cooked.
My point is that the smiley-guy approach only works when the target of your smile feels safe. What might work at a dinner party or bar doesn't translate well on a deserted mountain trail or in a dark alley—or even on a well-lit path. In the course of a normal day, we broads have to put up with a lot of crap: "Let me eat your pussy," "Nice titties, shortie," "What's the matter—you think you're too good for me—bitch!" etc. Let's just say that for the most part, it's a lot easier on a girl's psyche to avoid eye contact with her fellow man.
A few years ago, I went through a brief Pollyanna phase where I started to get bummed out by all the frowns and too-cool-for-school, attitude-laced faces surrounding me. I concocted an experiment wherein I would walk down the busiest, most hipster-laden street in my neighborhood and flash a smile at everyone who crossed my path. I brought along a girlfriend to objectively gauge my progress (left to my own devices, I would just assume everyone was charmed by my winning grin). I figured I'd spread a little joy. I figured wrong.
I quickly found out that people weren't charmed—not by a long shot. Moms with babies were the most patient, as they're used to strangers pulling stupid faces at their kids; but Tim, they weren't happy to see me—they merely tolerated my presence. As I rambled down the street, flashing my pearly whites at one and all, random pedestrians gave me funny looks and high-school girls openly pointed and laughed. Several extremely inebriated toothless gents seemed to find me irresistible (which they proved by following me, howling obscenities). The most disappointing reaction of all was from my target audience: the Hottie Boy. Cute guys actually seemed a little alarmed at my glee and went out of their way to avoid passing too close.
Three blocks in and I was ready to throw in the towel, but Mama didn't raise no quitter. "I think people are going to start wondering who that nice, happy girl is," I informed Chloe, as we noticed an old woman clutch her purse closer to her side. "I think people are going to start wondering who the retarded girl is," Ms. Thing smirked.
Ms. Thing had a point. I quit it and went back to my default grimace. See?
Your other rather large potential stumbling block is that you're exclusively in the market for younger babes. Unless they have a daddy fixation, most girls want boys—not old men. You've been misled by crusty old flapjack asses like Donald Trump and Michael Douglas scoring hot young tail. The difference between them and you is that they're fabulously wealthy and you're not. Therefore, it follows that they get supermodels and actresses—you don't.
So quit slobbering over every underage piece of ass that passes your way and get thee to a bar or a personals ad and pick on broads your own age. There's no fool like an old fool.
Dateless? Don't just grin and bear it: Write Dategirl at firstname.lastname@example.org or c/o Seattle Weekly, 1008 Western, Ste. 300, Seattle, WA 98104.