.Sleeping Around Craigslist

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

It takes a woman about a thousand words and a condom to get laid on Craigslist. But for a woman to be laid properly — by a passionate lover who knows what he’s doing — well, that’s a whole different ball game.

We are both middle-aged women who have spent the past eleven months sleeping around Craigslist. At an age when most women were sending their firstborns off to college, we found ourselves — through chance and circumstance — single, tumescent, and ripe for adventures. Those adventures have spanned ten counties and four states, and involved roughly 45,000 e-mailed words, 27 phone calls, 36 face-to-face initial dates, 13 actual lovers, and re-aggravated our carpal tunnel syndrome from all the typing.

Years before embarking on Craigslist, both of us had experienced sexual abandonment. We were both hungry for intimacy and physical touch after years of wandering in the desert. Our lives were on similar trajectories.

Lily Penza, 46, had been overweight since her teens and suffered from dangerously low self-esteem. At age 28, she moved in with the first man who looked her way. It was a virtually sexless union for ten years before a therapist helped her come to her senses and move on. Lily never married and spent most of her life caring for an ill parent who died recently. So she lost forty pounds and decided she would make up for lost time.

Anna Reed is a fifty-year-old who, as a young woman, had been raped and pressured into sex during the so-called sexual revolution. She had read books on women’s sexuality — Barbach, Tisdale, Jong, Hite, and Nin — but each held only a small piece of the puzzle. Not one of these authors could tell her as much about sexuality as her own inner life did. Emerging from a stale and sexless marriage, she would do things her way this time around.

Lily turned to the free Craigslist personals because didn’t want to spend any money getting laid. She started answering ads last July. She was open to every person and every experience — even Republicans, as long as they could kiss. Lily told her close friends about how thoroughly she would be sleeping around, joking “I want my vagina to have call-waiting.” Now she is enjoying the adolescence she never had; dating like an oversexed high school student but armed with the wisdom and savvy of a woman in her forties.

Anna decided to try Craigslist because she found other online dating sites too silly. Now, despite her wrinkles and middle-age spread, she “dates” a multitude of guys. But they aren’t really dates. “We don’t go places together, they sometimes buy lunch but just as often they don’t. I’m sleeping with them. Actually, that’s a euphemism; we have sex.” With a lover whose bad back has him on the injured reserve list, Anna knows what to do: click on “Casual Encounters” and start the e-mail banter that almost always leads to a meeting. “I don’t have a boyfriend,” she says, “I have a team roster.”

Lily and Anna are not our real names, but then you probably knew that was coming. Virtually everyone on Craigslist lies about something: their name, their age, their weight, their marital status, maybe even their penis or bra size. For the purposes of this story, we have changed everyone’s names to protect their privacy.

The two of us met when Anna answered an ad that Lily’s then-boyfriend, Scott, posted on Craigslist. Lily and Scott were seeking a third partner to join a ménage à trois. Before anybody actually met face-to-face, Lily dumped Scott and canceled the threesome, but she became e-mail pals with her would-have-been sex partner, Anna.

Once we met, we realized we had a lot in common, and began sharing our respective experiences. Our adventures have included the hot, the not-so-hot, and some potential hook-ups that never even got off the ground. There were memorable ones, like Lily’s first date, which ended at 3:30 a.m. at the Power Exchange sex club. Or the ex-con who went down on Anna for an hour straight.

There were forgettable ones too, like the alcoholic art dealer, or the guy who excused himself in the middle of sex to smoke a cigarette. And there have been multiple-partner dates, which involved average-looking East Bay residents who swing, tie up, dominate, submit, and spank.

What kind of sex did we find? Some of the lovemaking was wonderful, a lot of it was initially awkward but got better as time went on, and some of it was downright disastrous. Up-ending the notion of “Casual Encounters” — as Craigslist dubs its “Just Looking to Get Laid Tonight” category — we both discovered that casual sex is anything but.

Perhaps because we are highly verbal, our initial Craigslist encounters involved a ream of e-mail. Sometimes we just coordinated the logistics of the hook-up, but equally often, we wrote and received profoundly intimate and revealing letters — an epistolary of erotic stories.

Then there is the issue of sexual chemistry, which is arbitrary, inexplicable, and largely unpredictable. Terrific e-mail connections don’t guarantee a sizzling face-to-face meeting. And not everyone keeps their word. More than once, last-minute cancellations left us calling one another for support, or just drunk, horny, and alone with a DSL connection.

Finally, there’s the zany sitcom a woman’s life becomes when she’s juggling multiple lovers: scheduling dates; trying to keep personal data straight on each man; finding enough time after work to shave her legs, dye her hair, exfoliate her skin, apply mascara, and MapQuest the planned meeting spot.

But when it works — and it has — there is the sheer joy of exploring sexuality without any strings attached. And sometimes a woman can find a treasured friend with benefits, an outright boyfriend — or the love of her life.

Besides all the rules that sensible people follow when dating online, like “meet in a public place,” “let someone know where you are,” and “condoms are nonnegotiable,” we developed our own special list for middle-aged chicks who date on Craigslist:

1) A lot of men want to screw Sarah Silverman. (Three lovers told Lily the potty-mouthed comedian was their “fantasy fuck.”)

2) With ads for people over forty, add at least five years and ten pounds to the photo. That way, when the older and heavier date shows up, you won’t be as disappointed. This rule is as applicable to men as it is to women.

3) Men have a tendency to overreport the number of sex partners they have had. Women underreport.

4) You better have a good memory if you want to date a lot. In case you don’t, call everybody “honey” to avoid mix-ups and make a cheat sheet on each with the name of their dog, their favorite movies, wines, and sexual positions. Failure to take notes will make pillow talk a minefield. If you are compulsive, go ahead and make a chart.

5) Promise little, deliver much.

What We Found

Probably because the ads are free and largely uncensored, Craigslist has become “Hook-Up Central” on the Web. There’s no long questionnaire and no profile required as there is on other dating sites. There’s just a bunch of hungry people looking for everything — large breasts, big dicks, big beautiful women, skinny transvestites, long-term partners, friends with benefits, illicit affairs, spankable lovers, submissive studs.

The unspoken acronyms behind online personals are HIV, HPV, HSV, and HepB. Sexually transmitted diseases are the scourge of the modern gal navigating her way around Craigslist. Studies show one of the highest rates of new HIV transmissions is currently among women over forty. Just as a middle-aged woman knows she is ultimately responsible for her own orgasm, she also knows she alone is responsible for her own sexual safety. If a man won’t agree to wear a condom during sex, the thinking woman gets out of bed, gets dressed, says goodbye, and doesn’t look back.

Some people who date on Craigslist are careful, some are not. Some couples want full blood work and a credit check before they’ll swing; other couples bone strangers at the Power Exchange with just a few words beforehand.

But for a heterosexual woman who wants to get safely laid, there’s a fully stocked candy store on Craigslist waiting to be robbed blind. On a recent Sunday night there were 1,000 men in the Bay Area looking for one woman, any woman.

Most of the ads were written in a vulgar and tasteless style which didn’t even tempt an answer. For instance: “I often travel and find myself bored in a hotel room and not really interested in another half-assed handjob from some pregnant meth-head for $100. … So, I’m doing something very uncharacteristic: thinking ahead.” This man seemed to be looking for women to meet him in his hotel room the next time he was in town. His ad said he was “well-versed in the appropriate acts and mechanics” and able to “control myself so that everyone has a good time.” But though we like a man who is proud of his skills, he pissed us off by equating us with hookers. And his characterization of prostitutes as “pregnant meth-heads” is incredibly offensive.

Other ads were more tender: “Please, I feel so lonely,” or “Please I just want to hold you.” Many of the men who post on Craigslist are married, and some are upfront about it. There is an endless variety of enticing, amusing, and erotic messages. It’s never dull.

Neither of us ran our own ads; it was more fun to see what the guys were offering. Lily answered ads in the Men Seeking Women section while Anna looked in Casual Encounters. Anna was okay with the explicit nature of that milieu, and the ratio of men to women worked in her favor. Anna thinks like a guy anyway: have sex first; if that works out, see if love follows.

Nearly every Craigslist ad included the poster’s alleged age and geographical location. We answered ads that ranged stylistically: some were hilariously funny and tongue-in-cheek; some showed intelligence and creativity; others were just plain romantic. A good vocabulary excited us: one guy claimed he was a “naughty sesquipedalian.” A very funny ad entitled “Hideous Freak of Nature Seeks Sympathy Sex” included a surprisingly attractive photo of a buff male torso in briefs. Often one of us was the only woman to respond to an ad — that is, the only real woman. There are enterprising escorts, cyber-bots, and pay-to-view porn scams galore that spam male posters.

Many ads have photos, not just prose. This tactic increases the chances the posting will be read, but not necessarily that it will be answered. After all, the most common picture is the erect phallus. But, without a ruler or other scale reference in the photograph, a gal is skeptical. You also find narcissists in cyber-space: “You will suck my cock. You will lick my balls. You will do it all to ME.” C’mon guys, you’ve gotta give us a reason to hit the reply button. What’s in it for us?

Once we answered ads, we sought photos right away; no need to invest 2,000 words in someone whose face or body didn’t appeal to us. We sent current G-rated portraits to a new contact. Current is the key word here; people on Craigslist frequently post photos taken at least ten years earlier, or photos too dark or too far away to show details. Men send photos posing in front of motorcycles, sports cars, and boats; we’re guessing they think these props boost their sex appeal or give the impression that they have money. We didn’t give a whit about the props; it was the smile, the pose, the overall confidence that drew us in. The tackiest photo is a picture of a guy smiling with a woman’s arm over his shoulder, but the rest of her is cropped out.

The web etiquette we prefer: a compliment from a guy when they received our photo, as preparation for stage two. Flattery is nine-tenths of seduction. Sometimes a man’s picture isn’t as enticing as his ad or his initial verbal foreplay, so a friendly but firm rejection is in order: “I don’t think this is going to progress any further, but I wish you good luck and happy hunting.”

Did we use the now-clichéd “three-date wait” before going to bed with the men we met online? Not always. Did we throw out the rule book, cloth cover and all, and go against the advice of every therapist, professional matchmaker, and guest on Oprah by sleeping with men too soon? Yes we did. There is animosity in online forums about this; some women complain that women who bed men on Craigslist right away are spoiling the dating scene. They claim that if men don’t have to buy dinner or court a woman in order to get her in bed, they won’t. It’s the old why-buy-the-cow-when-the-milk-is-free argument, to which we say, “Give us a break.” We didn’t intend to upset the natural order. We just wanted to have fun.

And, now, some of the dates:

A Cunnilingus Expert

One of the first posts Anna answered was from a 55-year-old guy who said he would be happy to give cunnilingus for an hour — no reciprocation needed — and he was “not weird.”

Anna: “I love cunnilingus. But after an hour I would need … something else. Are you for real?”

Arthur: “Yes, I am for real … girlfriends have remarked how uh, dedicated I am when it comes to that activity. I thought it would be fun to find someone who appreciates that. So tell me about you!”

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.

The former was the first Craigslist date who understood that the largest sex organ in Lily’s body wasn’t between her legs. Last summer, Luke spent weekends on his boat at the Berkeley Marina and he and Lily started dating. Luke knew how to deal with a smart woman; if he didn’t touch her brain, he wouldn’t be touching her body. He was funny, audacious, and he kept Lily engaged and interested, in bed and out of it.

Lily and Luke fell in love. It was synchronicity: they both wanted the same thing — and it wasn’t monogamy. Although they live in different states, they still see each other once a month for passionate lovemaking — and lots of adventures; indoor skydiving in Union City, Raiders games at the Coliseum, halibut fishing on the San Francisco Bay, hunting in remote areas of Washington state, and dancing to live music, from Ben Harper at the Paramount Theatre to jazz at Yoshi’s.

While seeing Luke, Lily answered Carl’s ad. Carl was at the other end of the commitment spectrum: he wanted monogamy and he wanted it right away. Shortly after meeting Lily, Carl took his ad off Craigslist, professed that he loved her, and started introducing her to his friends and family.

Carl thought Lily was “The One” for him and he was upset she wanted to keep dating other men. He put more and more pressure on her to date him exclusively and get serious. Had she entered a strange parallel universe where the guy wants a relationship and the chick just wants sex? “At a minimum, I need a situation with a friendship that’s beyond a booty call between boink buddies,” Carl wrote.

Does the double standard really still hold in 2008? Can a man belt-notch and think he’s “sowing his wild oats,” but when a woman does the same thing, she exposes herself to being called a slut? Are we all still in high school?

Lily ran this by Anna. “I would prefer the term “sex-positive feminist,” but you can call me a slut if you have to, because there just isn’t a word for it in the English language,” Anna said. “Maybe ‘love goddess’ would be a good alternate.” Lily prefers the term “Supertramp,” largely because she likes really bad ’70s music.

This poses a larger question: is promiscuity really possible for women without attachment forming? There’s no easy answer. Anna admitted she fell in love “at least a little bit” with every man she slept with. Women are complex social creatures and our sexuality often requires some emotional or cerebral connection beyond just skin and friction. But there has to be friction.

And with Carl, there was some seriously good friction. Carl was expert at orgasm-inducing foreplay. He was a technician with a mission: he helped Lily find her G-spot, and then went further and found her elusive A-spot (a cluster of nerve endings located about halfway between a woman’s G-spot and her cervix). Tip: look for a man with really long fingers.

Lily was sprung. She told Carl “I love you.” But she knew in her heart she really should have said, “I lust you.” Out of bed, Carl was controlling, possessive, a chronic complainer, and could be rather boring. The complete truth was, Lily loved Carl because he was an amazing lover.

She continued to date him for the great sex, but the strain of lying to him took its toll. Guilt stopped her orgasms, even when Carl worked hard to get her there. She was foiled by the mind-body connection. After a weekend of whale watching in Monterey, during which it became painfully clear they were totally incompatible out of the sack, Lily broke up with Carl.

Time is limited, especially for a middle-aged woman, Lily realized. She felt she had wasted three months with a guy who drove her crazy by day — even if he also drove her crazy at night. Carl did not take it well: he sent her scathing e-mails and filled her answering machine with accusatory messages.

After the break-up, Lily was getting closer to knowing what she didn’t want. And with Luke, Lily got closer to knowing what she did want.

Lily turned to Anna for advice, who urged her not to settle. Anna also reminded Lily that while they are both late to the game, there’s still plenty of time on the game clock.

Ménage à Trois

Despite the languid, Henry-and-June, Paris-in-the-rain romanticism that surrounds the ménage-à-trois fantasy, Anna had to type e-mails for months to try to set one up. She contacted twelve couples and four pairs of men, but not one of these e-mail exchanges led to a single three-way tryst.

Threesomes are a pervasive male fantasy — check out any porn film if you need confirmation. It also is a common post from couples with a female partner harboring bisexual feelings. Anna herself had been pushing away bisexual feelings for many years, and decided she would finally explore them.

Anna used to live as if there were a paradise in the afterlife, but now she lived as if her name were already listed in the hotel register in Hell. Maybe this set-up wouldn’t lead to true love, but it would certainly be interesting.

She found that one person was usually much more into the idea of a three-way than their partner. Sometimes it was a man or a woman talking their significant other into trying something a little different on Saturday night. “First we’ll post, then we’ll decide whether we want to do it.” That’s the kind of attitude you get when the ads are free.

Before going to a meeting. Anna always asked to hear from the silent partner. She wanted to be sure that everyone who was there wanted to be there. If the eager party couldn’t get the recalcitrant party to turn up online, what were the chances of getting them to show up naked?

Anna didn’t have a whole lot of meetings. She answered one ad from a couple based in Oregon and met them face-to-face at Peet’s on Fourth Street. They divulged that they didn’t believe in condoms. Anna could handle garden-variety atheists, but how can you not believe in condoms?

When wooing, pairs of men were much better coordinated than couples. Two men would successfully tag-team Anna in e-mail exchanges until a meeting could be arranged. Among the dates that never went all the way:

Anna drove in the pouring rain to Chow in Lafayette to have beers with Bill and Richard, the friendly, oh-so-normal guy-next-door team. It would be easy to imagine Richard standing behind you at the hardware store, Bill standing in front. Either way, it doesn’t matter as the three-way never came about.

Next came happy hour in Sausalito with two overprivileged captains of venture capital. Kevin was quite handsome and aloof. His partner, Neil, owned a yacht and was old enough to be her dad. Anna noticed people at the next table staring at her from behind the men’s camel hair jackets. They were listening. As he left, Neil discovered he knew the couple at the next table. Yikes.

Anna had an urbane terrace lunch with Steve, 46, and Mark, 55, at Oliveto’s in Rockridge. Unfortunately, Anna found the waiter ten times more irresistible than her dates. Silver-haired Mark interested her, but she couldn’t imagine kissing Steve. Now that’s a bit awkward all around.

In the end, Anna found these threesome meetings rattling. It isn’t easy to flirt with two guys at the same time. And not every pair of men were effective at getting to the rendezvous:

Dick, Chuck, and Anna exchanged a staggering 105 e-mail messages, but only two were written by Chuck. After weeks of voluminous correspondence, Dick finally revealed he had lost his partner. It seemed that Chuck had fallen in lust for Dick. Anna wondered why he hadn’t entertained that as a possible outcome from the get-go.


Undeterred, Dick went ahead and answered a foursome ad with Anna as his new buddy.

Paul and Missy were an attractive middle-aged married couple. Dick jumped into an e-mail correspondence with Missy and pretty soon the four found themselves seated around a table of raw oysters at Pearl on College Avenue. The evening went surprisingly well: Missy, 47, was chatty, funny, and friendly. Paul, fifty, resembled Anna’s childhood TV star crush — Bob Crane, the colonel from “Hogan’s Heroes” who always got the girl.

The next day Missy followed up in an e-mail: “Dear Anna and Dick: Would you be willing for us all to get a STD panel done to share — so we know what each has or doesn’t have?” What a buzz kill.

But in a subsequent e-mail Missy revealed that her first husband had contracted HIV and died of AIDS from secret affairs he had had during their marriage. Although she was HIV-negative, Missy had understandably deep concerns about STDs, so the four would lay their cards out on the table. (Missy even forwarded Paul’s test results via e-mail as a PDF.)

Anna trooped to the Berkeley Free Clinic for her HIV test. She squirmed when she realized she was old enough to be the intake counselor’s mother. Anna tried to explain why a condom wasn’t always an easy sell with men in her age bracket — largely because they never had to wear condoms during the go-go ’70s. The 25-year-old counselor nodded her head, but it was clear that Anna wasn’t gapping the generational differences in sexual mores. Anna was sent off with fistfuls of condoms in every color: mint-flavored, lubricated, ribbed, and twisted. She did learn one thing: not to floss her teeth before, during, or after sex, to reduce the risk of oral-genital virus transmission.

The big night finally came for Dick and Anna to drive to Missy and Paul’s condo in San Francisco. Of course, they didn’t all have identical chronic STD profiles. What would be the odds of that anyway? Undaunted, Anna brought along every safe sex device available at Good Vibrations; dental dams, lickable lube, vibrators, Saran Wrap, and all those free condoms. That night, Anna shared a peak sexual experience that crushed her bones to stardust.

The next day, Anna visualized her happy future in a group marriage, but that lasted a nanosecond. The interpersonal dynamics of four naked people were exponentially more complicated than a relationship between just two people; and most of us know what a picnic that can be sometimes. In the morning-after e-mails, it was clear Missy felt the swinging foursome was a one-time event, although Anna would have liked to have seen the couple again for another go-round.

The Life Lessons

After we decided to collaborate on this article, the number of dates we went on fell way off. It’s tough to find time to have sex when you’re writing about it.

Lily dated Luke exclusively in the past few months. Their love grew deeper when, in April, Luke was handed an unexpected diagnosis of kidney disease. What started out as casual sex on a boat in the Berkeley Marina, ended up as friendship caught fire. Hearts can and will be broken when sleeping around Craigslist. And in love, just as in life, there are no guarantees.

Anna remains in the game full-time. We are publishing under pseudonyms to protect our kids and our day jobs, not because we have shame. Truth is, we are grateful to be having the passionate sex we missed when we were younger. We thank the men and women we have met on our journeys. And we share the real list of what we’ve learned:

Be yourself.

Trust your body and your intuition.

Be honest with your feelings.

Practice safe sex.

“No” is a complete sentence.

Have fun.


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