At the end of the night, as we made goodbye-small-talk by Linda’s car, I fretted over the hug or kiss question. I’d had a nice time, but I could tell I wasn’t passionate about this girl. It felt strange to be only getting to know Linda when she was already certain she liked me. I decided to go with a hug, to take things slow, so I could catch up.
I leaned toward her with my arms in hugging position, but found her chin pointed up, her eyes closed, and her lips prepared. Okay, I can give her a little peck good night; that doesn’t send any big message. Before I could pull away, Linda grabbed the back of my head and enveloped me in a full-on makeout session.
When we finished, she asked if I was free Wednesday.
“I’m not sure. . . . I’d have to check my calendar. . . .”
“Okay,” she said, staring at me. She wanted me to check right then. I pulled out my phone.
“I guess I’m free.”
“Great! My friends and I are going to a beer-tasting concert event. You should come.”
I could learn a thing or two from Linda. She’d gotten a makeout session and a second date out of me when I wasn’t sure about either—the girl was a closer.
* * *
When I spotted Linda in the back corner of the brew pub, my stomach dropped—I’d walked right into a trap. Four female friends sat around her like a royal court. I tried to hug Linda hello and she again snuck in a kiss. One of her friends “aahed” while another “oohed.” I ordered food, but thirty minutes after my hamburger arrived it remained almost untouched, as I’d been too busy answering questions to eat. This wasn’t a social hangout; it was the Silver Lake Inquisition. Her friends were measuring my worthiness for dating Linda. The matter of whether I wanted to date Linda was not taken into consideration.
At the end of the night, I overheard my good reviews as Linda hugged her friends goodbye—He’s great; a keeper; so nice. It did feel good to pass a test, even one I hadn’t wanted to take in the first place. Linda texted me before I got home, telling me what a good time she’d had and how much her friends liked me. Apparently, she wasn’t familiar with the dating technique known as “playing hard to get.”
It was two weeks before I saw Linda again, a purposeful break to slow things down. I was using a technique called Plotting Points, which I’d learned from Grant (the friend who told me about Burning Man). The idea behind Plotting Points is that it’s not the number of dates that signifies the seriousness of a relationship, but the frequency of those dates. Three dates in a week means something different from three dates in a month, despite the number of dates being the same.
How to Plot Points in a Relationship
1. No more than one date per week. At this pace, the relationship can remain casual for a long time.
2. Don’t make specific plans for the next date while on the current date.
3. Maintain continuity between dates by keeping in touch via text.
4. When you do set the date, make it a few days or a week in the future, buying further time while confirming interest.
The goal of Plotting Points is to avoid having The Talk for as long as possible. And sometimes, when Plotting Points is executed well enough, the actions have spoken loud enough to render The Talk unnecessary. If you see someone less often than you take your garbage out, it’s probably not a very serious relationship.
After being “busy” (playing a new video game) for a couple weeks, I set a date to see a movie with Linda. The time away hadn’t dampened her excitement. She spent the whole movie stroking my hand with her thumb, laughter and soft looks punctuated dinner, and at the end of the night she invited me into her apartment.
“I like you,” she said, stroking my hair during a break from kissing.
“I like you too.” I said it out of instinct, but instantly knew my “like” did not equal her “like.”
For guys, the beginning of dating can feel like a series of trials they must pass to earn the approval of the girl. Wouldn’t it be nice to avoid all that? With Linda I had. Dating her was like being preapproved for a credit card. No credit check necessary, just start spending.
But in reality, the one-sided nature made me uncomfortable. It felt like my desire to be a couple was irrelevant because she’d already made up her mind. And despite her certainty, I knew she didn’t like the “real” me because she didn’t know the “real” me. No, she liked the idea of me, the me she’d seen onstage, me at my wittiest and most charming. I’d kept up the performance for three dates, but I couldn’t play the role forever.
After my recent experience with Amber, I didn’t want to lead someone on again, so I left without having sex, because no matter how well I Plotted Points, Linda wouldn’t get the message. I broke it off a few days later. The lack of hate-filled text messages told me I was improving.
I was happy with my progress as a responsible casual dater, but I did have one regret. My first encounter with a “groupie” had ended without my having done the one thing you’re supposed to do with a groupie—have sex. I should have at least snorted some cocaine off her breasts in the back of my tour bus. Of course, I’d never done cocaine and didn’t have a tour bus. Maybe I could have eaten ice cream off her breasts in the back of my Jetta? That’s kind of punk rock, right? Though, the problem there is that ice cream can get pretty messy and it would be a pain for her to clean the stickiness off. NO, STOP IT, MATTESON! You’re being too nice. Cleaning chocolate syrup and peanuts off your breasts is the price you pay for getting close to a STAR! (Or the host of a nonprofit storytelling show with a small following.)
10
* * *
THE SLAYING OF HIGH-SCHOOL-MATTESON
“I’m going to see Michelle Glimmermen next week,” I said as I dug into my waffle with fig syrup.
“Who’s Michelle Glimmermen?” Kurt asked.
“Uh, she’s only the prettiest girl in school.”
I told Evan and Kurt the tale.
* * *
On the first day of Christmas break my senior year of high school, my friends and I planned a party at my friend Pedro’s house. Behind his family’s main house was an old bunkhouse, a remnant from the property’s days as a ranch, which they’d transformed into a sort of rumpus room, with old shag carpet and a mishmash of garage sale furniture. We had spent many nights hanging out there, doing what teenage boys do—playing video games and passing gas.
But this party was going to be different from the average fart-fest. Pedro’s little sister, Melanie, who was two grades younger than us, was going to be there with her friends, including Michelle Glimmermen.
Michelle Glimmermen had created a stir when she’d shown up at school in the fall. Beautiful, tall, and athletic, she had the glow of youth but the body of an early-bloomer adult. I thought she was the prettiest girl in school, which meant she might as well be the prettiest girl in the world. Smarts (all honors classes) and a great laugh, deep and loud, rounded out the total package that was Michelle Glimmermen.
Before the girls arrived, there was much jockeying between my friends over who would hook up with whom. The one person I knew for sure wouldn’t be getting lucky was me. At that point I’d never kissed a girl, so I had little optimism I’d bone down, boink, take the piggy to the market, do the humpty dance, knock boots, lay pipe, pork, ride the baloney pony, score, or [insert any other horrible term teenage boys use for sex acts].
The party started slow, with the boys and girls segregated, but a suggestion by Pedro that we use the hot tub livened things up. The listed capacity was four, but we fit in ten people, making a warm soup of teenage hormones with slippery legs intertwining under the surface. Boys’ legs being as hairless as girls’ at that age meant it was often impossible to tell whose leg it was under the bubbles, but it was still exciting.
Because the hot tub was so full, girls were sitting on laps, and Michelle Glimmermen ended up on mine. I thought it must be an accident, that she’d only chosen my lap because no other option was open, but we talked and joked an
d she never got up, even when a seat was available.
While having the prettiest girl in school sitting on my lap thrilled me, I had a constant worry about getting an erection. It’s ironic that men spend the last twenty years of their lives hoping they can get a boner, but the first twenty often praying they won’t. There’s millions to be made with a reverse Viagra for teenagers: To be boner-free, take one pill before math class or a school dance. If your nonboner lasts more than four hours, steal the Victoria’s Secret catalog from your mom’s mail pile.
If I needed further confirmation of Michelle Glimmermen’s interest, it came when we were back inside and she asked if I wanted a massage.
“Sure, but only if you want to,” I said, giving her a chance to correct the mistake I assumed had occurred.
“Here, lay your head down in my lap.”
As I lay there, the number 73 popped into my head. My friend Ron had often cited studies showing that 73% of massages between men and women resulted in a sexual interaction. This stat was probably bullshit, but because of Ron’s confidence and specificity, I believed it. Surely, some university was running a massage-to-hookup experiment and crunching the numbers. And that meant I had a 73% chance of hooking up with Michelle Glimmermen.
Her hands moved in mirrored circles around both sides of my head, her fingernails scratching under my hair. My body tingled from the Jacuzzi, and my feet, positioned close to the fireplace, were toasty. I’d never been so comfy or happy.
Sometime after 2:00 a.m., people settled themselves for sleeping. The choice spots on the couches went fast, leaving only the floor for most of us. Michelle Glimmermen and I ended up next to each other, forced close by the limited space. After lights-out, I could hear the sounds of blankets shuffling and pairs of feet sneaking off to the bathroom. All around me people were getting it on. This was my moment.
But I did nothing.
I could have reached over and rubbed her back or whispered to her or spooned up next to her, but I did none of those things. Instead, every few minutes I’d open one eye and stare longingly. I was terrified she’d catch me, but also hoped I’d find her staring back. I only stopped looking when the sound of her breathing told me she was asleep.
* * *
“And nothing ever happened with her after that?” Kurt asked.
“We were sort of flirty at school for a couple weeks, but then she made out with this basketball player Jack Coleman.”
“Jack Coleman. He sounds like a real dick,” Evan said.
Jack Coleman was a real dick! Like a high-school movie cliché, I’d lost the girl to the asshole jock. I hated him, but I wasn’t angry with Michelle Glimmermen. We weren’t a couple, and for all she knew, I was a eunuch.
“And you’re seeing this girl when you go home for Christmas?” Kurt asked.
“Yes, I am.”
I hadn’t kept in touch with Michelle Glimmermen over the years, other than sporadic Facebook interactions, but a month earlier we’d met up at a party when she had visited LA. We’d gotten along well, so I’d asked her if she’d go on a date with me when I was home for the holidays. Though of course I didn’t call it a date.
“We should hang out when I’m in town,” I’d said.
Translation of the Phrases Guys Use when Setting Up an “Innocent” Social Interaction
• Let’s chill = Let’s date
• Wanna hang out? = Wanna date?
• We should get together = We should get together . . . for a date.
• We should grab a drink/bite/snack/meal = We should grab a drink/bite/snack/meal and I will pay for the drink/bite/snack/meal and that will mean we’re on a date.
• I was thinking of going to that new play. Would you want to come? = I would never go to a play, but I think it will entice you into a date with me and make you think I’m sophisticated.
• Do you want to go hiking this weekend? = No one except a Sherpa has ever gone hiking except as a date, so we will be on a date.
• Can you help me move this weekend? = Can you help me move this weekend? (It’s hard to find people to help you move.)
And so, I was getting a drink (going on a date) with Michelle Glimmermen a few days after I arrived in Colorado.
* * *
From our cozy booth Michelle Glimmermen and I could see the fat flakes of snow meandering to the already white ground outside. We had been at the bar for more than three hours, but neither of us wanted to face the reality of goodbye and the cold weather.
Of all the women I’d dated since my experiment began, Michelle Glimmermen was my favorite yet. Her laugh was as sublime and generous as it had been in high school and she had the vivid complexion, smoldering eyes, and wide smile I remembered. Even her body looked relatively the same, kept trim by yoga.
In stark contrast to the sweaty interactions of my teen years, the evening was calm and comfortable, thanks to my new dating confidence. Knowing when or how to make a move didn’t worry me. I could enjoy our date, certain I’d know what to do when the time came. And I very much hoped the time would come. In some small way, hooking up as an adult would help me to finally erase the cowardice of High-School-Matteson. Though I wasn’t angry with Michelle Glimmermen for choosing Jack Coleman over me, I hadn’t forgotten the pain it caused me. (Obviously. I mean, I am writing about it in a book.)
On the walk back to her apartment, where I’d parked my car, I offered my arm and she took it. Our conversation dwindled as we enjoyed the tranquillity of a world quieted by fresh snow.
“Would you like to come in?” she asked when we reached her doorstep.
I instantly dropped seventy pounds and the hair in my armpits fell out. I was no longer the thirty-year-old conqueror of online dating, the guy with a fuck buddy and a groupie, but once again the undersized and overwhelmed High-School-Matteson. I clinched my hands inside of my pockets, trying to get “Sure” to pop out of my mouth. I thought I’d gotten over this type of anxiety, but this wasn’t just some girl from OkCupid; this was Michelle Glimmermen, the hottest girl in school.
Luckily, she saved me by saying, “I have the latest episode of Mad Men on my DVR. We could watch that.”
Yes, TV. I was going inside to watch TV. High-School-Matteson could watch TV.
“I love Mad Men,” I said. “That’d be great.”
* * *
We cuddled up under a blanket, watching the episode. Soon we were kissing and as we made out, High-School-Matteson returned, not as a naysayer, but as an awestruck fan. Holy shit, Future Matteson, you’re making out with Michelle Glimmermen! Take that, Jack Coleman!
We removed our shirts, but the makeout session didn’t progress further, fitting for a hookup with a high-school crush. Afterward we lay next to each other and talked about our almost-fling years earlier. She had indeed liked me, but had been as scared and unsure of the dating process as I.
“When we didn’t hook up at the party, I figured you didn’t like me like that.”
“And then Jack Coleman,” I said.
“Yeah. It just kind of happened. He was forward. Not in a creepy way—he just knew what he was doing. No offense.”
“None taken.” (Some taken.)
“It made it easy. I did feel a little guilty, though. And to this day, he’s my dad’s least favorite boyfriend, if that makes you feel better.” (A little.)
We cuddled and talked for a while longer, but eventually I had to go home. There were holiday responsibilities to tend to the next day, like wrapping presents and making sure I was buzzed enough to deal with my stepmom.
“Well, thanks for living in LA,” she said as we got dressed. I could hear in her voice the same regret I was feeling about the unlikelihood this would happen again.
I should have felt triumphant as I drove away—I’d finally made out with Michelle Glimmermen. It wasn’t merely a victory for me, but for every shy Nice Guy dumped by a girl for a jock. I was like the Braveheart of awkward teens, though instead of “Freedom!” I would yell “Second Bas
e!”
But I didn’t feel like I’d “won.” Over the course of the evening she’d stopped being Michelle Glimmermen, the hottest girl in school, and became Michelle, a girl I liked but couldn’t date because of circumstance. There was potential between us, like in high school, but it would remain unrealized. That didn’t feel like “winning.” It felt disappointing.
(Okay, it felt a little like winning. I mean, after all, I had made out with THE Michelle Glimmermen. Suck on that, Jack Coleman!)
11
* * *
THE “WHAT-IF?” GIRL
Years earlier, before my year of being single, before Kelly . . .
I was living in New York City and had been dating Ann for just over a year. It wasn’t going badly, but I could tell it wouldn’t last—neither of us had said, “I love you.” And a year is a long time to go without saying that to the person you’re dating. The more time passed, the more weight the word itself gained. Both of us had started avoiding saying the word love at all, in any context. We’d be like, “What a great egg sandwich, I really lo— like it. I liked that egg sandwich. It was very special to me.” It’s bad form to rank a breakfast sandwich above your partner emotionally.
Since we weren’t using the L-word, the cards we exchanged at our one-year anniversary dinner came out sounding like we were signing each other’s yearbooks. It’s been great getting to know you this year. Stay cool this summer. XOXO.
So, things weren’t good, but I certainly wasn’t going to break up with her, because I was still a Nice Guy at that point, and Nice Guys don’t do things that might be emotionally difficult.
One weekend, not long after that awkward anniversary dinner, Ann and I had plans to attend a concert with my roommate, Dustin, and his girlfriend, Kate Middleton. (When I was writing this book, “Kate” told me she wanted her fake name to be Kate Middleton, so here we are.) At the last minute, Ann had to go out of town for work, so the extra ticket went to Lindsay, a friend of Kate Middleton’s.
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