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?