When I posted my reply, the person I had in mind was Miss Washington Universe of 1969-70. I was in college, and was one of the yearbook photographers. The staff photog assigned me to do a shoot of this 6' tall platinum blonde knockout who had just been crowned Miss Washington State at the local Miss Universe/Miss USA pageant. Turns out she lived in the same dorm. We hit it off, she liked my quirky sense of humor, and I liked her sunny personality and how photogenic she was. She also was a lot smarter than your average model. We dated a few times, she was a frequent visitor to my dorm room, and after a couple of months she took up with my roommate, a 6'3" championship crew team member with a degree in pharmacy going for his MBA. They moved out of the dorm to live together off-campus.
In 1973, I was the layout editor and official mug shot photographer for The Daily Astorian in Astoria, Oregon. When Lois Feary came back from winning the Miss Teen Oregon pageant, I took the mug shots. And I asked her out. We dated a few times, but she was on the travel circuit and going to school, so we eventually lost touch.
Jamie Distefano was in the chorus and our belly dancer for the 2000 Sunnyvale production of Man of La Mancha. She had been Miss Santa Clara County 1999 and was twice in the top 10 finalists of the Miss California pageant. I was one of the leads in the show, and we hit it off from the start. But it was when she stumbled upon me playing the piano backstage before a rehearsal that she asked me out. We had one date, and she invited me to a party at her place, but as soon as the show was over she reportedly moved back to Twain Harte out in the Sierra foothills to be with her dad, and I have not been able to locate her since.
Edit: This picture is not a very good one of her, but it's her second Miss CA appearance, this time as Miss Mission City in 2001. Here is a slightly better view.
SO I have two or three points to make. First, for those women who make the excuse that men don't ask them out because men have fairy tale dreams about dating supermodels, you can put that excuse in the shredder. Second, supermodels are not all airheads who are only in it for the cash and to be the Toy Boy's Boy Toy. And third, I guess I'm not as shy as I always think of myself as being.