“Like on a real date?”
“A real-deal date.”
She claimed it was only the second “real date” of her life and set about getting ready. When she emerged from the bathroom, she looked like a different person, a stunner in makeup, heels, and a dress. I dressed up too, in a blazer and tie. After a week of weird dusty clothes in the desert, neither of us could believe how good we looked. As we sipped our nightcap after dinner, Alenka thanked me for the special bond we’d formed.
“I’ve never had an adventure like this,” she said. “I didn’t know such a relationship was possible.”
Neither of us had ideas about staying together long-distance. Though we got along well and had good sexual chemistry, we weren’t in love. We were friends who had sex and it was exactly what we both wanted. Like Burning Man itself, the finite nature of our time together had made it special. We toasted to not having ruined the friendship.
The next day, we drove to the Griffith Observatory, so she wouldn’t be a total failure as an LA tourist, and then headed to the airport. Because of traffic, our goodbye was rushed. No long speeches, no promises to stay in touch, just one last kiss, a wave, and she was gone through the sliding door.
In the past ten days I’d tried drugs, fallen in love with a man, seen a motorized cupcake, and had a lot of sex. Quite an adventure. I mean, yes, it would have been cool to get involved with a fuck-pile, but overall, a great experience.
Part III
* * *
AM I THE SLEAZY GUY?
17
* * *
WHY QUIT WHEN YOU’RE AHEAD?
After Alenka departed, I was left to face the consequences of my revelry. I’d lost five pounds and was suffering occasional bouts of vertigo, due to mild dehydration. My sunburned skin was starting to peel and a sleep deficit had me yawning every fifteen minutes. I barely left my apartment as I dealt with a weeklong hangover.
When I recovered, the Bros’ Brunch reconvened and I told Kurt and Evan all about Burning Man, sparing only the details about my relationship with Brian (no need to make them jealous). When I’d finished, I asked what they’d been up to.
“Not much,” Evan said.
“I went home with a girl from a bar last week,” Kurt reported. “That was fun. Probably won’t see her again. But, in other news, I got a new meditation pillow—it’s great!”
Kurt proved once again he was the wisest of us all.
“So, Burning Man was the end of your self-imposed year of being single,” Evan said. “Are you going to try to find a relationship now?”
During my recovery week, I’d thought this over. Was it time to move past all this, to settle back down? I was in my thirties, after all. In my hometown, bachelors over thirty had to wear a red B on their chest so they could be easily identified and set up with someone’s niece.
But I lived in LA, where being single in your thirties wasn’t weird. In fact, it was an advantage. Unmarried, gainfully employed, nonasshole guys over the age of twenty-eight were valuable commodities. But wanting to stay single wasn’t just about being a scarce resource; I also felt more confident than I ever had.
For the first time in my life I didn’t feel like a boy playing an adult in a high-school play. I lived alone, cooked for myself, could afford premium cable, owned blazers, and washed my sheets on a regular basis. With a Gentleman Résumé like this, I expected to be knighted any day.
“I’m at the height of my powers,” I told the guys. “Why would I give up casual dating?”
“For love or companionship or true intimacy?” Evan said.
As I dipped my French toast into cinnamon guava syrup, I waved him off.
“Who needs those dumb things?”
* * *
Because I’d let relationships lapse as I prepared for Burning Man, I had to start with a clean slate. Expecting the usual low response rate, I messaged a dozen women at once. Because of luck or improved technique, I got several responses and ended up with three first dates on three consecutive nights.
A year earlier, this would have seemed an impossible task. Back then I had needed at least forty-eight hours of mental prep before each date to harden my psyche against nervousness and possible rejection. But now I wasn’t anxious at all. I knew what to wear, where to go, the pathos to emote, and the jokes to tell. Dating was now like building an IKEA desk, simple and easy, with a successful end product almost assured.
Three nights in a row I went to a different bar and met a different girl and had the same experience: The same awkward hello; the same discussion of childhood, families, and hometowns; the same explanation of career, goals, and frustrations; the same hugs goodbye and proclamations of “This was fun we should do it again”; the same follow-up texts.
I didn’t experience amazing chemistry with any of the girls, but that was okay. I’d become so good at mimicking what it’s like to connect that I didn’t need to actually connect anymore. I could create a successful date by recognizing patterns and reacting to them.
PATTERN RECOGNIZED: Date opens up about family.
RUN PROGRAM: Talk about parents’ divorce and seem vulnerable.
PATTERN RECOGNIZED: Date enjoys travel.
RUN PROGRAM: Tell funny story about backpacking in Europe.
PATTERN RECOGNIZED: Date is talking about profession.
RUN PROGRAM: Ask lots of questions and seem fascinated.
PATTERN RECOGNIZED: Date likes the Twilight series.
RUN PROGRAM: Pretend that’s not ridiculous.
PATTERN RECOGNIZED: Date complains about prior relationships.
RUN PROGRAM: Tell story that shows I’ve suffered similar pain, but that indicates optimism remains.
MASK DATA: Possible emptiness of soul.
* * *
A lot of people, maybe even most, dislike dating, but I loved it. After my three dates in three nights, I finally understood why: the charge I was getting from dating was very similar to the one I got from performing live. In both cases I was seeking validation by persuading strangers to like me using a well-practiced routine. As a comedian, the validation came in the form of laughter; with women, in getting a second date.
This realization gave me pause. Just as there’s something unnatural about wanting to perform in front of strangers (it’s many people’s greatest fear), maybe dating so much was abnormal too. Maybe it was a defense mechanism. After all, if you’re no one’s boyfriend, you can’t be anyone’s ex-boyfriend. For the first time, I wondered if my “experiment” might be unhealthy. Was I changing my relationship pattern or just filling a void with the affection of strangers?
Well, no time to contemplate that now—I had three second dates to go on!
* * *
The word casual in casual dating implies it is easy and laid-back, but the opposite is true. To do casual dating properly, one must be disciplined and organized.
Keys for dating several people at once:
• DO remember that continuity matters—If you can’t see someone often, stay in touch. No contact at all for over a week will kill most relationships.
• DON’T just text—In a world of text messaging, a phone call feels special. A phone call? My, my, this thoughtful person must have been trained in Britain’s most prestigious politeness school! Plus, phone calls get you a quick answer so you can move on to the next person if the first is busy.
• DO make definitive plans—When dating multiple people there can be no “we should get together sometime this week.” That’s how you end up with scheduling conflicts. Find out what night your date is free and schedule a specific event and time. This has the added bonus of showing decisiveness.
• DON’T make booty calls—Unless it’s been explicitly discussed that the relationship is sex-only, nobody likes to feel like they’re only being contacted because of horniness. Make plans that involve more than having sex (even if you’ll mostly be having sex).
• DO own two sets of sheets—I know this one is kind of scumbaggy
, but it’s a good tip. For both sanitary and aesthetic reasons. Sometimes you might not have time to do a load of laundry between dates.
• DON’T make a spreadsheet—At times it will be tempting. Keeping everything straight will be difficult, but remember, turning people into data points is never a good idea.
• DO protect your phone—Set your phone so it locks and there are no previews of texts or emails. Sure, both people might know it’s a casual fling, but breaking the fourth wall will ruin the mood.
On my string of second dates I had a hard time keeping things straight. Who was the assistant at the production company? Was it Brenda or the other brunette I took to the cocktail bar? And which one did I kiss? I’m almost certain I kissed one of them. It was a microcosm of my whole dating experience—everything was starting to blend together.
The second dates all went well, but one stood out. At the end of the night, the short brunette, Brenda, invited me to her apartment, but prefaced the invite by saying, “Nothing’s going to happen.” This wasn’t the first time I’d heard this phrase during my dating time. What “Nothing’s going to happen” means is “Everything’s going to happen except actual intercourse.”
At the height of a heated, mostly naked makeout session, while caught up in the moment, I blurted out something I never thought I’d say.
“When we have sex I’m going to fuck you so hard.”
WHO HAD I BECOME? Who talks like that except a private detective in a Cinemax soft-core porn?
I nearly apologized right after I said it. I’d always tried to be a Nice Guy not only on “the street,” but also “between the sheets.” Brenda didn’t seem to mind, though—she kissed me harder and the intensity of our session increased. I became forceful in my actions and she matched my roughness at every turn.
When I’d started my year of dating I’d believed women should be treated delicately during sex, as if made of papier-mâché. This belief stemmed from movies, which had convinced me as a youngster that the ultimate in sexual romance for a woman was slow and gentle lovemaking on a bed of roses. But for Brenda, passion and assertiveness trumped politeness.
At the end of the night, as I kissed her goodbye, Brenda grinned and said, “You’re trouble.” This made me feel very cool.
That’s right, lady, I’m trouble. Sexy Trouble. Yeah, I’m the kind of trouble that sticks with you, that don’t wash off with soap. No, you’re going to need a scalding hot bath with baking soda to get rid of this trouble. Wait, maybe now I’m describing poison oak? Anyway, you get the picture. I was TROUBLE.
Brenda asked when we could go out again.
“We’ll see,” was all I said, because Trouble don’t stick to a schedule. But, then again, Trouble did have to take his Volkswagen Jetta in for service next week, which would complicate things. Might be best for Trouble to pencil something in.
The next time I saw Brenda it was part of a different kind of back-to-back than my three dates in three nights—I had sex with different women on consecutive nights. Brenda was the first, followed the next night by Sonya, the girl I’d been with when I ran into Kelly. I had to admit that it thrilled me a bit, to be this “good” at getting girls, but with the excitement came qualms. Though I’d made no promises of exclusivity to either woman, they’d probably be bothered by what I’d done. Plus, feeling prideful about it felt icky. These were people I was dating, not achievements to unlock in a video game. Was it possible to be too good at dating?
18
* * *
A FEW RED FLAGS
We all have emotional baggage; it’s nothing to be ashamed of. The bad things that happen to us and the poor decisions we make may shape us, but they don’t have to define us. But, broadcast problems too soon and they become Red Flags. A girl I was dating, Wendy, had more Red Flags than a Chinese military parade:
• At age twenty-nine, she was currently living with her mother. RED FLAG
• She became blackout drunk on almost a weekly basis. RED FLAG
• She brought up and talked about—at length—not one but two ex-boyfriends. RED FLAG
• She had moved in with one of the ex-boyfriends after a week of dating him and he turned out to be gay. RED FLAG.
• She dated the other ex-boyfriend for over a year despite its being an extremely volatile relationship. RED FLAG
• She readily admitted she was not over her last boyfriend. RED FLAG
If Wendy and I had been together for six months by the time I heard all this, I wouldn’t have cared. But we hadn’t been together for six months. We hadn’t been together for six hours. She revealed all of this on our first date. Which wasn’t even a date.
I’d run into Wendy at a hipster dance club in Silver Lake, where, instead of velvet ropes, bottle service, and techno, they have skinny jeans, PBR, and mash-ups of Vampire Weekend. Wendy and I knew each other, but barely, having met through friends a couple times. After a few hours of dancing, I suggested going back to my place for a drink and she accepted.
We were on my couch, sipping beers, the dance-induced sweat on our shirts still drying, when she began to unload all her Red Flags at once. It was more therapy session than conversation as everything flowed from her in a long monologue prompted by my probing question, “Where do you live?”
When she finished speaking I comforted her, told her she was a great person who deserved to be happy, and drove her home. One night of physical pleasure wasn’t worth the risk of engaging with someone who had so much to sort out emotionally.
NO . . . WAIT . . . That’s not what happened at all.
Instead, I waited until the conversation came to a lull and kissed her. One night of physical pleasure was TOTALLY worth whatever fallout might come. When you’re not interested in a relationship, a Red Flag can look a lot like a Green Light.
The makeout session was one of the strangest I’d ever experienced, aggressive and passionate, but, at Wendy’s request, fully clothed. We were doing sex positions—missionary, doggy style, reverse cowgirl—but in our clothes, practicing the Dry Hump Kama Sutra. It was so unusual, I didn’t know if I should count it as another Red Flag or not.
* * *
Judging by all the Red Flags, at best Wendy was a little kooky and at worst a big old pile of hot mess. After our first rendezvous I knew there was no way we’d have a serious relationship, but we had nice physical chemistry, even with our clothes on, so I asked her out again, which meant finding more Red Flags.
On our next date she told me all about how she’d once worked at a bar as a paid “date.” Men would come into the club and choose a girl to be his social companion for the evening, talking to him, fetching him drinks, and dancing with him. She never had sex with a client, because she didn’t want to and it was against the official rules, but other girls often did. I didn’t mind that she’d had this job, but a second date is when you talk about childhood fears, not the icky feeling you got from being a pseudo sex worker. Red Flag.
After dinner we returned to my house and started fooling around, this time removing clothing. There was biting, scratching, and hair pulling, which I’d experienced before, though not with such animalistic fervor. It frightened me a bit, but excited me as well.
Wendy explained that she liked to be physically dominated in bed, but not degraded. She enjoyed dirty talk, but didn’t want to be called a slut or a whore—kink without misogyny. While pinning down her hands I would think about how women deserve equal pay in the workplace.
When things got heated, Wendy pulled away.
“I’m trying to be good,” she said. “I’ve had sex too quickly in the past and I don’t want to do that anymore. How many people have you had sex with?” (Too early to be discussing this—Red Flag.)
Having almost doubled my lifetime sex number in slightly over a year, I proudly reported I’d slept with thirteen people in my life.
“Yeah, see, that’s barely anything. I’ve slept with A LOT more than that.”
Wendy left late that night
and after I walked her to her car, I went to the bathroom to brush my teeth. As I began brushing, I noticed something—a small bruise on my right biceps. There was another one on my shoulder. I moved my gaze from my arm to the mirror and I froze—my body was covered in dozens of hickeys.
Toothpaste dripped from my agape mouth as I examined the damage in the mirror. There were small blue bruises, crescent arches of teeth marks, and long red stripes made by fingernails. I’d known things had gotten a little rough, but this looked like I’d just gotten home from a hard day of octopus wrangling.
Normally, this wouldn’t have been an issue, as they were all in places I could cover with a shirt, but I was flying to Mexico the next day for a family beach vacation. And so, at 3:00 a.m., I googled “How do you get rid of hickeys?” The consensus on the internet was to alternate between using ice (to reduce swelling) and rubbing the marks with a bare hand (to increase blood flow and reduce discoloration). I sat on my bathtub doing both things for two hours. I tried other suggestions too, such as using a hair dryer, applying a warm tea bag, and patting the hickeys with a hairbrush. It all seemed unlikely to work, but it was either this or convince my family that turtlenecks were the newest chic beachwear. Oh yeah, the neck-du-turtle is all the rage in the French Riviera this year.
By the time I went to bed I’d made some progress and the next morning all but a persistent few had faded. My dad commented on one, but I blamed it on getting hit with a racquetball, and though it wasn’t 1988, he bought it.
These are the kind of things you deal with when you ignore Red Flags.
* * *
Of course, that didn’t stop me from seeing her again. But after a couple more dates, Wendy did something REALLY crazy. She told people we were dating.
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