The Mother of ‘Em All

Taylor, in her late 30s, is an executive assistant in Boston and knows her way around a mouse pad. She’s employed several sites in her quest for companionship but met this gem on AdultFriendFinder.com.

“He was hot, in his mid-30s and worked as a financial guru,” she says. “We spoke a number of times, had great phone conversations and phone sex, and when he asked me out for our first real date he said he planned to pull out all the stops.”

To her delight, he showed up at her office for the event in a limousine with roses in hand. “All the girls were so jealous!” she remembers. “We walk downstairs, he opens the door for me and his fucking MOTHER is in the limo, too!”

“She’s only joining us for dinner,” he told her. “Then you and I can cruise Beacon Hill for a night cap.”

Stunned and horrified, she grabbed her coat and got out of the car. “He called me for days trying to explain that he and his mom are really close and she was just excited to meet me after he told her how well our conversations went. But I mean—on a date? A first date?! FREAK!”

The Wrankle File

“When I think of this guy, I just can’t help but remember that Seinfeld episode where Jerry goes out with this beautiful girl, but can’t get over the fact that she has man-hands,” laughs Rae, 33, a veteran online dater from Northern California who doesn’t consider herself all that picky. In fact, this entire episode, which happened three years ago, was something of a private embarrassment. She is referring to Wrankles, a date with whom at first there seemed potential.

“He had a great smile and wonderful sense of humor. We had a nice date—actually went out on Valentine’s Day—to a winery and had some lunch,” she remembers. “He was nice and not bad looking—a few extra pounds but he biked and worked out, so I could get over that. But it was just—his wrists!”

They were so unbelievably thick she found herself distracted. “I was watching him using the fork over lunch,” she says, laughing and readily admitting the absurdity of the situation. “They were like cankles on his arms, so I just thought, ‘wrankles.’ I was sure at that point I’d crossed some kind of line and would be single forever.”

Months later, as fate would have it, her friend was set up with the same guy by another person. “I had never told anyone about the ‘wrankle’ issue out of self-preservation,” she says, “but when we realized we’d gone out with the same man, she told me she’d noticed the same thing and couldn’t get past it, either.”

Fast-forward to pretty recently: A new neighbor moves in up the block. “I was walking my dog and noticed a red Cherokee with an Obama sticker. Good sign, I thought, and hoped for a young, single gentleman. I see a familiar blond man coming out to say hello and slowly I put the car and the face together and realize, Holy shit! It’s Wrankles! Living on my fricking street!”

She sighs. “Eight doors down. Too bad I couldn’t get over the wrankles.”

Too Much of a Good Thing

Be careful what you wish for.

When Taylor (she has an arsenal of oddballs) met Jeff, she thought there was genuine promise. They talked constantly for a month, exchanged clean pictures and decided to meet. “We had a great time and began dating regularly,” she says. “Two months in, I was absolutely ready to sleep with him – but he hadn’t tried anything!”

One night, after a date, she decided to be the aggressor and asked him up to her apartment. “We started making out and before long, I was naked and he was still completely dressed!” The action stopped and Taylor asked him what was wrong. Jeff said he had something to confess. Her heart sank.

“Turns out his big confession is that he had an absolutely giant penis and wanted to warn me of his freakish proportions,” she says. Jeff explained that in the past he’d lost many girlfriends because they felt his member was “difficult to work with.”

At this point, suspecting he was a little full of himself, she insisted on having a look. Reluctantly, he removed his pants.

“He unleashed the fucking Kraken,” she says, without a trace of irony. “His dick was enormous! I couldn’t see the end of it! There was no way that was going into any of my orifices.”

The two got dressed and went downstairs to the diner. “I bought him a piece of pie,” she jokes, “because that was the only kind he was getting from me that night!”

Photo Finished

People, seriously. Use a current photo of yourself. Why waste your own time, let alone someone else’s? I spoke with dozens of people in my research and the number-one complaint was that the date would show up and look nothing like the images they’d been posting online.

Submitted for your approval: Sterling, a 36-year-old writer who, bored and “mostly” single, decided to throw out a line on Craigslist one night to see what might bite. A few e-mails, pictures and phone calls later, she knocked on his door.

“The picture must have been taken in a previous life,” he says, “because she had gained well over 100 pounds, was a solid 10 years older than advertised and looked and smelled like she hadn’t showered in at least a week. Not even a Pez dispenser full of Cialis was going to get me through this one. But I’m a sucker for a good story. I bade her enter, anyway.”

Ten minutes later, she threw herself on him. “Slobbering and humming and wanting a big ol’ bag of stuff I wasn’t prepared to provide, but managed to get out of it with the one man-trick we rarely share.”

He faked a back injury.

“A bit of wincing and hobbling later, and she was gone.”

In Bondage

Although she is now happily married with a couple of rugrats, 10 years ago, Vivienne—a structural engineer—was in her late 20s, a Brit expat living alone in New York. “And I had just been dumped by my fiancé—spectacularly,” she laughs. Although proficient in the ways of the Web—she’d even enjoyed some chat-room fun in the early days of AOL (“I ended up having really good phone sex with this guy in the Bay Area of California,” she confesses, “but honestly when I heard his voice I wondered if he was even old enough to be in college…!”)—she had never employed the Internet as a dating tool but decided to take the plunge.

Before long she had a bevy of suitors, but one stood out. “After a couple of days of online chat, we started talking on the phone.” They’d forged a nice report bonding over their love of movies, particularly older ones.

“He was very witty and he knew more useless trivia than I did,” Vivienne remembers. At one point, the conversation turned to old Bond films and she mentioned that she’d always had a thing for Sean Connery. “He immediately lays into the most spot-on Connery impersonation you could ever imagine. It was perfect. And as silly as it seems, it turned me on in the worst way!”

For weeks, the two continued the dance—online and on the phone. Throughout the courtship, he would use the accent. “He’d leave me messages, calling me ‘Moneypenny’ and that sort of thing. I got a bang out of it, you know?” Finally, they made plans for a date.

“He showed up at my flat and he wasn’t the most dashing guy in the world, but his looks were nice, and it was him, after all—the guy I’d been speaking with for more than a month. I knew him. I liked him.”

The date—dinner, followed by several pints and rounds of pool—led right back to her apartment. “I had this nagging feeling in the back of my head that it might be a mistake, but I was tipsy and didn’t want to listen,” she admits. “We fell in the door pawing at one another. The clothes fell away quickly and we were in my bed.”

Once there, in the dark, the lanky salesman morphed into someone else entirely. “I was up on top of him, bouncing away” she says. “At that point I’d already thrown caution to the wind and so I was going to go out with a bang if he wasn’t going to call again, you know? And then in the middle of the whole thing, he starts dirty-talking, which I’m mostly okay with—except he was doing it in the Connery voice!”

She was amused “for about 4 seconds,” she says, “but then, as I’m riding him, he’s not stopping. ‘Fuck me, Moneypenny,’ he’s saying, and then on and on with these really dirty things—all the while in the bloody accent. It was just—weird. And I was going to stop, but he worked himself up so doing the Bond thing, he came straightaway. Before I could help it, I laughed.”

After that, it was awkward. There wasn’t much eye contact. He sort of skulked out in a hurry muttering that he’d call me, which he did, actually—but three days later—and it was clear he had his tail between his legs about the whole thing. I might even have blown it off had he not been so odd about it.”

They never spoke again. “But he did leave his VHS copy of “Dr. No” at my place,” she laughs. “I still love the old films but since then that Scot accent just doesn’t do it for me the way it used to.”