The Guy With The List, mid-30s.

Guy’s ad was the first one I ever answered. Except for a one-nighter with someone I met at a conference two days after I filed my divorce papers, no one had touched me since my soon-to-be-ex-husband. I’d been window shopping for men through the Salon and Nerve personals, but as I tried to compose saucy little notes to entice the appealing ones into checking out my I’m-smart-but-don’t-take-myself-too-seriously, I’m-sexy-but-pretendingnot-to-be-slutty, I’m-intriguing-but-not-pretentious electronic persona, I felt as self-conscious as I would trying to pick up a man in a bar—something I have never, ever been good at. Plus, everyone seemed to be checking the “serious relationship” box, and that could not have been less what I was after. When I heard I could spend a few Thursday afternoon hours on Craigslist’s “Casual Encounters” section and line up three dates for the weekend, the appeal was undeniable.

So, Guy: His ad noted that he was also going through a divorce. He seemed funny and sweet and more than a little sad. Which all sounded good to me: I was still feelin’ fragile.

We exchanged a few emails and made plans to meet at the Tunnel Top—I’m a sucker for a dive bar that makes its drinks with fresh citrus— which, as it turned out, was around the corner from his apartment. I knew from the minute he sat down next to me at the bar that it wasn’t going to happen. (Yes, it’s judgmental of me, but bad chemistry is bad chemistry, and it’s instantly recognizable.) But this being my first such date, I had not yet mastered the etiquette of sticking out my hand after one drink and saying, “Hey, it was really nice to meet you, but I don’t think there’s any chemistry here. So I’m gonna head out.” Plus, I was lonely and it was kinda comforting to talk to another recently heartbroken person, even about superficial things. I drank three of the Tunnel Top’s delicious cocktails, and then stumbled back to Guy’s dim, carpeted studio apartment, with its desk in the closet and its old leather chair full of dirty clothes. There I ate some Cheez-Its and caught a glimpse of his self-improvement to-do list. The only entry I remember is “Be more successful with women,” which not only made me want to cry, but also pierced my vodka fog enough to make me realize how painfully I was leading Guy on by being in his apartment with no intention at all of making out with him. I made my apologies and left fast.

My Little Friend, a.k.a. the Selfish Prick, a.k.a. Yes, I Am Still in Touch with Him, and You Know, He’s Grown Up a Lot, 24.

Clearly, I should be calling this one by his actual name. Nick and I met up at the Albatross one Wednesday night following several phone calls full of hot but surreal banter. My interest was piqued when he brought up quadruple penetration thirty seconds into our first conversation, and I could tell he was impressed that I had taken the dare of not hanging up on him for it. My hopes were up, and when I saw him standing outside the bar reminding me of the boy I’d lost my virginity to fourteen years before, I was flooded with lust—and relief that not all my blind dates were going to make me melancholy. We kept up the banter for a good two drinks, and I invited him back to my house.

Thus began our entanglement. Nick thrilled me and drove me crazy in equal measure. He was smart but arrogant (and not nearly as smart as he thought he was), contradicted himself constantly (including on the topic of what was going on between the two of us), and seemed to have no idea of how people normally relate to each other. Together we had some of the hottest sex of our lives, and what should have been a lighthearted three-week fling turned into six months of kink, mutual manipulation, and strip Boggle. I knew it was over when I called him up one December evening, laid up with a tremendous head cold. All my friends had left town for the holidays, and I had brought him juice on more than one middle-of-the-night occasion. “You want me to bring you soup?” he asked. “Yes, please,” I said. “I’m strokin’ it,” he replied. “I’ll call you later.” He did call me later. More than a month later, with the gall to be surprised when I told him I didn’t particularly want to hear from him. “I thought we had a friendship that was pretty permanent,” he lamented. “Friends bring friends soup when they’re sick, even if they’ve been interrupted while masturbating,” I corrected. He claimed not to remember the incident.

The intensity of the sexual chemistry kept me calling or returning calls from Nick for almost three years, during the first of which we would make desultory small talk before sussing out the likelihood of getting naked. Eventually, though, our conversations became less about what I was wearing or whether his cock was hard and more about the challenges of being a young, inexperienced white teacher in predominantly black classrooms or the frustrations of my job in the nonprofit-industrial complex.

Now that he’s more mature and less arrogant, he actually is as smart as he thinks he is, and I sometimes feel a pang for our missed opportunity. But when he calls me after a breakup and describes in vivid detail all the enticing things he wants to do with me, only to rescind the offer of a visit a week later, I remember why I have already vowed half a dozen times never to call him again.

Mr. Call And Hang Up, 31.

Oh, how I love caller ID. We had shared some fantasies over email, but he was clearly ambivalent about acting on them. I finally had to email him: “If you want me to call you back, you have to leave me a message.” So he did, and we met up for one brief, slightly uncomfortable bout of mutual masturbation during which he never took off his little knit cap. Sometimes I see him walking down Telegraph, and when he looks right through me I don’t think he’s faking not remembering our evening together.

Dude Who Smelled Wrong, 29.

Dude was 20 minutes late to meet me at Dr. Bombay’s and didn’t even apologize—though I didn’t get off on the right foot, either, not saying “Hi, nice to meet you” before telling him that I had been about to give up and leave. It didn’t matter; he shared a scent with someone I had dated years before, with whom the sex had been absolutely terrible. This guy could have been the hottest, smartest, nicest straight boy in the whole Bay Area, but I was having sense memories of slobbery kisses and a flabby tongue. Our lack of interest was decidedly mutual, and I was out of there in time to catch up with my friends who were halfway through dinner at Pakwan.

Dreamy Mama’s Boy, 27.

I could not believe my luck when I met this one, he was so totally my type—skinny, curly hair, glasses, seemed kinda queer. Oh, and way messed in the head. But I didn’t know that yet when he walked into Mission Bar with his knitting project (“I wanted to have something to do if you were late,” he explained) and bowled me over with his sweet, smarty-pants, self-deprecating manner. When he asked me if I wanted to see his sublet, I was touched by the earnest euphemism, and further charmed by his breathy admission, after the kissing started, that “I’m so glad you like me.” We went to second base and I slept over; by morning I was so crushed out I was almost too nervous to ask if I could see him again. I was even undeterred when he said he would have to consult with his therapist. Lucky for me she gave the go-ahead, and I entered full-on compulsive-emailchecking, holding-evenings-open-for-unconfirmed-non-plans, thinkingabout-touching-his-hair-when-I-should-have-been-working mode. Even though we were getting progressively more naked each time we hung out, and trading flirtatious emails in between, I sensed ambivalence, and it made me nervous. When I brought it up, he wrote, “I’m trying to tease out how I feel about physical appearances versus personalities. But, that said, what went down the other day was pretty fantastic in a way that I’d never experienced before.…We can be friends. Or ambiguous friends.” Translation: I’m not attracted to you but I really loved it when you stuck your finger in my ass, so I’d like to reserve the right to mess around when I feel like it. When I ran my interpretation by him, he corrected me: “Actually, you physically resemble (a young version of) my mom. And it turns me on. And scares me.” Yeah. Okay. Bye.

Perfect Technique Man, 34.

Man made me realize that I might be even more messed in the head than the Mama’s Boy. He was interested in hanging out once or twice a week; could hold up his end of a conversation very well; made it clear just how very attracted to me he was; and was honest, straightforward, and selfaware. The cherry on top of his cake was that he loved giving head more than anything else, and he was damn good at it. So why didn’t I think he was dreamy? I don’t know, but perfect technique only gets you so far. There were lots of orgasms, but no sparks. I had to end it before it made me feel totally dead inside.

Transatlantic Phone Sex Buddy, 26.

When we got close to making an in-person date he was suddenly called back home to London to care for an ailing family member. He wouldn’t give me his phone number and never said when he was going to be back in town. But: British accent. ’Nuff said.

The One Who Licked My Face When He Came, 33.

Needless to say, I did not see him again.

My Anarchist Bike Messenger Friend, 23

I actually kinda fell for this one, a sweet, sweet young man who rode all the way from Virginia to San Francisco on his bike. He was shy and straight-laced on the surface, but in between rounds of surprisingly hot sex, we talked politics and our histories of depression. I learned about his Catholic family and his three middle names. We curled up together in my hammock and smoked cigarettes. When he left that night, accepting neither the option to stay over nor a lift back to the apartment share where he was camping out on the couch (“No, I feel like I need to ride”), I thought we were gonna see lots of each other, maybe hold hands while taking long walks to good dumpster-diving spots. But it turned out that MABMF’s strong-silent-type façade masked an intense skittishness; turns out he wasn’t quite as ready for casual sex as he had thought.

Several months later, he got in touch to say that he was interested in giving it another shot, and that he could explain what he called “my whole nerves/stress/sex thing.” So we went back to the scene of our first date (the Ruby Room again), he explained, and I took him home for what was some very tender sex. For some stupid reason I didn’t see the freak-out coming. But it came anyway.

For a while, we would collide somehow—we would see each other on the BART platform, or I would email him about the Friendster-posted picture of his new tattoo—and end up back at my house, fucking. I would call him the next day, making a joke about how I was checking in to make sure he wasn’t freaking out. He would declare a desire to hang out more, and then evade my future calls. It’s been about two and a half years since we met, but it’s only been a few months since I stopped lazily daydreaming about him in idle horny moments, his lean biker’s body and incongruous coital sweetness. Last week I saw him outside the MacArthur BART station, perched on his bike, doing that pedal-forward-pedal-backward balancing thing while he talked to some cyclist buddies. I turned and walked the other way.

Tribeca Grand Guy, 25.

I was in New York on vacation, he was in New York on business. I was apparently the only non-hooker to answer his ad. He was an amazing dirty-talker. I swiped a bottle of hotel moisturizer on my way out.

Free Palestine Activist, 19.

The political conversation was incredibly interesting, the sex, not so much. It was cool to meet someone idealistic enough to believe that one integrated, democratic Jewish-Arab state could exist, but after our run-in, I decided that all my dates had to be at least 22.

Gay Porn Addict, early 30s.

Given my penchant for queer boys, I thought someone who was exploring his straight side after a decade of homo sex would be just the ticket. We met at Mission Bar late on a Saturday afternoon. I’d never been there during the day before; the contrast between the bright daylight and the bar’s cave-like atmosphere should have been enough to send me back home to Oakland.

The GPA was pretty cute, but almost too gay for me (which is saying a lot), with his tight, striped shirt and tinted glasses. We took a cab to his apartment. He showed me some of his porn collection, both professional and homemade. Clothes came off, I touched myself, he contemplated touching himself, and…nothing. “I told you I was going to be shy and you’d have to make the first move,” he said. But I couldn’t make a move when he seemed much happier to sit there in his underwear and watch porn. He chivalrously paid for a cab back to the BART station, and I promised myself not to attempt any more sex with men who don’t have a confirmed attraction to women.

The Boys, mid-30s.

The Boys were close friends who—though they were vehemently opposed to touching each other and any positions that might lead to any accidental touching of each other—liked threesomes. At a yuppie brew pub in San Rafael, I drank a glass of wine and watched Boy #2 eat the burger Boy #1 bought for him while I decided that I felt safe enough to go back to Boy #1’s apartment with them and finally, finally, finally get something I had wanted ever since that day in high school swim practice when I stood behind Dan Weiss and his slightly sleazy best friend, checking out both their asses at once and huffing their fumes of postpubescent near-homoeroticism.

The Other Boys, early 30s and somewhere around 50.

Since the original Boys wouldn’t touch each other, I figured I should find some boys who would. Though this was theoretically the scenario that made me hotter than anything, I was just not all that turned on watching OB #2 suck OB #1’s cock. I was supposed to be providing expertise and instruction; I went through the motions of commentary and even got kinda into sucking OB #1’s cock myself, but in the end, all I got from it was the resolve to do that again with men I think are hot.

The next day, OB #1 emailed me to ask if I would suck his cock again. When I politely declined, he offered to buy me dinner. Um, no.

The Wake-Up Call, 30-ish.

I knew five minutes into the date that it was all wrong, but somehow I couldn’t stop myself. There he was, sitting across the Elbo Room table from me, making himself available. My reservations only increased on the BART ride back to my house, as he kneaded my thigh and talked about not being a “one-pump chump.” I soldiered on, observing my own arousal in a detached and slightly horrified way. Even though WUC was skeezing me out, I wanted to get laid and I was gonna get laid no matter what. Back at my house, he lacerated my face with his needle-sharp stubble and dripped sweat onto my stomach. I was having no fun at all, and though I think I was faking it pretty well, he didn’t seem surprised when I nervously called a halt to the proceedings (no matter how many “you have the right to revoke your consent at any point during an encounter” trainings you go to in college, it’s still hard to kick a guy out of bed mid-stroke). In fact, I think he was relieved, cheerily observing that he could still catch the last BART home.

After the Wake-Up Call, I met a few people through the course of regular, in-the-flesh life, but between the Cutest Web Designer Ever (a friend of a friend visiting from an East Coast city) and the Huge Mistake (clearly needs no further explication), I saw how little difference it made. I dabbled in other dating sites, sometimes still cruising Casual Encounters late at night as if it might provide something satisfying. I even responded to a few ads, vowing each time to be pickier and slower to shed my clothes. That’s how I met the Kid with the Van (failed attempt on the slow-toshed-clothes tip, but oh, what a great kisser), the Biology Grad Student (turned out to be more interested in the conquest than the sex), the English Grad Student (I ended it after six months when he faked orgasm one night), and the One I Can’t Write About Because I’m Still Too Crushed Out Even Though It’s Over. I’ve just vowed yet again not to call Nick anymore. It might be time to move.