Sleeping Around Craigslist 

Two middle-aged women discover that casual sex is anything but casual.

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Anna: "Okay ... when I was in high school, my first sexual experience was in the back of a Chevy when my boyfriend went down on me; he initiated me to my first orgasm. I've never found anyone who was nearly that, um, dedicated. If you are for real, it would be wonderful."

And wonderful it was. Arthur was intuitive and long-lasting. Plus he was a sweet guy. What's not to like?

Mr. Fit

Meanwhile, Lily met a 57-year-old self-described "Sensually Charming Man" whose ad read "Fit/Athletic, mild mannered, financially and emotionally secure, and sensitive." Their rendezvous was at the Lafayette Reservoir where, strangely, Mr. Fit became quite winded after the first slight grade change. Perhaps his definition of being "athletic" involved sitting on the couch watching sports. While they connected intellectually, Mr. Fit accused Lily of misrepresentation.

"In your e-mail you said your eyes were green," he told her. "But they are actually hazel."

Lily didn't call him out on his own apparent exaggeration of his fitness level; she just smiled and said her goodbyes. She chalked it up to a good walk spoiled. Later, channeling her inner-bitch, she realized she should have said to Mr. Fit: "Don't worry about the color of my eyes — you won't be looking into them ever again."

Erection Dysfunction Junction

Phil's e-mails and phone calls with Lily were irreverent and spontaneous. He gave great e-mail. A former art dealer, Phil and Lily discussed de Kooning and Franz Kline. They discovered they both loved Richard Thompson's music. Phil wrote that his ideal woman was a cross between "the shiksa goddess Diane Keaton, and Sarah Silverman." Lily, who is brunette and funny, thought she and Phil might be a great connection.

When they met for the first time at Peet's coffee, Lily was nervous because they seemed so perfect for each other. Phil, on the other hand, was utterly mellow.

"Wow! You are so relaxed," Lily told him.

Phil's response: "I had a shot of scotch before I got here."

Their date was at 12 noon. Maybe Phil had confused a bottle from his liquor cabinet with his mouthwash? Since they were so compatible — and they were physically attracted to each other — Lily proceeded with the date as planned. Later that evening, when they made it back to his place, Phil poured them each a glass of brandy and got to the business of pleasing Lily. But his penis had made other plans.

The problem of erectile dysfunction looms large among men of a certain age. It's difficult for men and women not to take it personally. It wasn't just Phil; erectile dysfunction surfaced in a few dates. What we don't understand is, why don't men with this problem compensate by developing other skills, like oral sex or French kissing?

Anna concluded that erectile dysfunction might be the great equalizer: "It makes older men more vulnerable now, more human than when they were young and at the top of their game."

Some men look to better living through chemicals: One of Anna's lovers with an erratic erection brought his little blue pills by the fourth date. Another guy, a 49-year-old from Hercules, accidentally dropped a half tablet of Viagra out of his pocket when he was making out with Lily on her bed. He was mortified — he apparently hadn't planned on telling her he might need to enhance his erection — although Lily was fine with it. The awkwardness of the moment subsided, but killed the date.

Younger Guys

The cure for old guys with erectile dysfunction is younger guys. Trouble is, sometimes they have erectile dysfunction too. A younger guy is not a get-out-of-jail-free card. There are a fair number of attractive, fun men in their thirties and forties who post on Craigslist looking to hook up with a woman ten or fifteen years their senior.

Dylan: "I just happen to like the dynamic. It's not a fetish or a fantasy. I'm looking for a casual physical relationship that also involves interesting conversation, and older women generally have more life experience to learn from."

A younger man knows that the alarm bell rang on an older woman's biological clock years ago. She already has the kids, the career, the house, the car. Of course, none of that may keep him from dropping her like a hot potato when a younger woman enters the scene. When Anna finally met the 41-year-old Tim face-to-face on the San Francisco Embarcadero after four weeks of hot e-mail, she whacked him with her tote bag when he admitted he had backed out of earlier plans because he had slept with a younger woman instead. The bitter irony: he had suffered erectile dysfunction.

"That's for being stupid enough to think that a twenty-year-old woman would be a better lay than a fifty-year-old woman," Anna said, grinning at Tim. "And this is for realizing you screwed that up," she added, kissing him.

A Tale of Two Men

Lily met two men on Craigslist who would rock her world: Luke, who restored her faith in romantic love; and Carl, who made her want to change her phone number, pull the covers over her head, and never go on another date again. Some relationships enhance your life while others diminish and deplete you.

Luke, 48, from Washington, honored and celebrated the righteous, smart, pretty, fun-loving woman he saw in Lily. Carl, who never did cop to his real age, but was well over sixty, made her feel like a hostage.

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