When I graduated high school sexually inactive, my grandfather was terribly disappointed.

“This is because you went to Catholic school,” he told me. “They messed you up.”

The fact I went to Catholic school bothered my grandfather, who was concerned that I was turning my back on my Jewish heritage. Jews, he explained, are not as conservative sexually and thus not haunted by whatever evil spirit was keeping me sexless. So, in an attempt to show him that I hadn’t betrayed him, I made a concerted effort to lose my virginity in college.

Here’s a tip: When trying to sleep with college girls, don’t mention that you’re trying to bed them to prove something to your grandfather. This “creeps them out.”

So, unable to reason with women, I tried the next best thing. I got really drunk on cheap beer and tried dancing at frat parties. And where there’s cheap beer and dark rooms and loud music, there are dance floor make-out sessions. After a steady record of evening tongue action, my grandfather was still not convinced of my commitment to our faith.

“How is most of America having sex by your age and not you?” he asked, rubbing my sexual insecurities in my face. “You damn Catholics are too afraid of hell.” To rectify this, he told me, he would set me up with some easy women.

Fun fact: if you strike out with a girl your own grandfather thought was “easy,” you may not be cut out for sex.

I was about to explain to him that it wasn’t the fear of hell that kept me a boy and not a man. Instead, the opportunity just never presented itself. But instead I got set up on a date with a girl that made it clear in the middle of dinner what her intentions were.

“I’m hoping to get married as soon as possible,” she said.

That didn’t make me feel comfortable. Though her demeanor during dinner was very cold and professional, she invited me back to her place for some of the most robotic kissing I have ever had. It was like kissing a vibrator whose batteries were dying. Since I was not a sexual connoisseur, I really only had refined tastes in kissing and assorted other “hookup things to do.” And, call me a snob, but I needed more than the Kissbot 9000.

I tried to explain this to my grandfather when I told him I didn’t want to date that girl again.

“My God, what is wrong with you? Do you know how old I was or your father was when we lost our virginities?”

Important knowledge: never ask that question and, if that question gets asked to you, never ever say yes.

So it turns out that my father and grandfather lost their virginities before I did — my grandfather pointed out that this took place before the birth control pill. I wanted to tell my grandfather that there was a whole ocean in between celibate and sex, and while I hadn’t yet slept with someone, I had my share of fun. But the problem is that while it’s occasionally appropriate to talk with family about sex, it’s nearly impossible to discuss the many other sexual things naked people can do. When these are the only other things you’re doing, it makes it hard to communicate that you’re not joining the priesthood and letting your Jewish ancestors down.

“Don’t you want to have children?” he asked me. “Do you know where children come from?” I wasn’t at the top of my college class, but I had an inkling. So to placate my grandfather, I let him set me up again.

This next girl and I had a lot in common. We liked the same movies, read the same books, and had the same grandmother. As it turns out, she was my cousin. When I had this realization, twenty minutes into dinner, I grabbed my cell phone and called my grandfather.

“Is this girl my cousin?” I asked.

“Yeah, by marriage. So?”

“This is gross.”

“She’s pretty and she’s smart and you of all people can’t be so picky,” he said. He had a point, but I wasn’t going to stoop that low. Perhaps I was a virgin, he suggested, because I was too choosy. If I disqualified women for such petty things as looks or being related to me, I would be a virgin forever. My grandfather insisted I could do worse. Best of all, he pointed out, she was Jewish.

I still said no, carefully reasserting that it wasn’t because she was Jewish but because she was a little too close to my tribe.

I eventually did have sex with someone outside of my family. But by the time I did, I had learned to appreciate the other aspects of a good hookup. Which made the pseudo-bar mitzvah my grandfather had for me bittersweet. So after the whiskey and celebratory prayers, I told him about some of my other adventures, trying to use as respectful language as I could while still getting my point across. He put his arm around me and told me he was proud.

Will Newman hosts a weekly podcast about making out which he, unabashedly, calls “Making Out With Will.“

Photo licensed under Wikimedia Commons.

Read more articles from Issue 08: “The Sex Issue.”

It was a cold December night. The girls were out in far too little clothing, hugging themselves and shivering as they walked around in their clackety heels. The wind, never overly sensitive to the sentimentalities of pedestrians, played coy, reclining just long enough to convince them to relax the tensing of shoulders and scrunching of necks before reappearing to lash at exposed skin. But one young man, just days shy of his 21st birthday, wasn’t suffering with the rest of them on the street. He was indoors, in the warmth of an East Village apartment, finally losing his virginity.

By 20, his virginity had gone from being that annoying family member your mom forces you to speak with during Passover dinner to the unwelcome friend you have crashing on your couch who traces your movements with sleepy eyes every time you walk into the kitchen to get a bowl of cereal in the morning.

“Dude, when are you going to find your own place?”

“What? I’m bothering you? You already want me to leave? I thought we were friends. We’ve known each other since we were kids man.”

“No, sorry, listen, that came out wrong, it’s just that-”

“You’ve changed. It’s really sad.”

He poured out his Honey Bunches of Oats/Cocoa Krispies mix and retreated back into his room.

–

Things with the girl had started off innocently enough. They met during the relative innocuousness of Taekwondo practice. Convinced by a friend to join the team, he showed up ready to find something new to occupy the waning days of senior year. She was a law student who looked nothing like someone called to mind by the word “taekwondo.” Basically, she was attractive, a girding-of-the-loins sort of attractive, and watching her kick and sweat and grunt for that first 2-hour practice didn’t necessarily alleviate any notions he started developing immediately upon meeting her.

But he was a good guy at heart, and he had a hard time reconciling the innate animalistic tendencies we all feel with the desire to be a gentleman. So after he finally left practice and got himself away from her physical presence, he started thinking less about how much he wanted to have sex with her and more about how he really just wanted to ask her out and, if he was lucky, maybe she’d become his…(giggle, giggle)…girlfriend.

Then again, who was he kidding? He was a kid next to this 23-year-old, law school-attending, “mature” woman. He didn’t think he had a chance, he didn’t even think she knew he existed outside of the awkward introduction during the first practice when he stuttered his name and quickly turned red. But on the other hand, there was nothing to lose, and having just climbed out of his post-pubescent years of acne and bad haircuts, he was finally feeling a little more confident in himself.

So, after a few weeks of holding kicking pads for her and accidental glances in each others’ direction, he finally asked her out. He had thought over in his head, a million times, about the least-stress-filled date environment he could find, and finally decided on something that was liable to make her feel totally at ease and score him some “nice Jewish boy” points – a dinner with a Chabad Rabbi and his family.

She came in clothing that made him look twice, at her legs, at her chest, at the line her neck made in its slide down towards her clavicle. During dinner, as the Rabbi’s kids bounced around between the dinner guests and tipped over hummus plates while reaching across the table for soda, the Rabbi’s wife smiled in their direction and nodded as if she was approving of this particular combination.

After dinner he suggested – offhandedly, thanks to the wine – that they visit a friend’s birthday party at a bar near Union Square. But it was only during their walk to the bar that he panicked from the realization that she didn’t actually know his real age, and that as the go-to-responsible one among his friends, he didn’t even have a fake ID.

“IDs please.”

He froze and stared up at the bouncer timidly. His mouth had gone dry.

It was at this exact moment when he was prepping himself for social disaster that the girl touched the bouncer’s arm and cooed in his ear – “He’s with me. Is that OK?”

A smile and a nod later, he was shocked to see the doors thrown open for them. Inside, he quickly wished the friend a happy birthday and proceeded to buy her a drink. She would only take whiskey, on the rocks, and he was too inexperienced at the time to fully understand what this meant. As she sipped on the drink, she pulled him onto the dance floor and drowned him in the deep twisting of her body in candle-lit corners. His head began to spin and he closed his eyes. His hands reached for her hips, desperate to get some grounding as the world seemed to slip from under him. And then, somehow, in the accidental turning of his head, his lips caught themselves on a spot just under her ear and she let out a light moan.

She didn’t invite him back to her place so much as tell him he was coming. And of course he followed her obediently, dragged by hand through that same winter lashing he would, in a few moments, be casually observing from inside her apartment. His feet moved methodically, stepping down from icy sidewalks onto icy streets and scraping their edges against the mesh metal webbing of overflowing garbage cans.

It all seemed surreal that this was actually happening. After all this time? He nodded to himself incredulously. As she led him into the 300 sq. ft. studio and shut the door, he felt the old shell of his world coming apart, sliding onto the floor. And even though he didn’t know all that much at 20, he knew that this was him, finally melting into manhood.

Photo by Mangui, licensed under Creative Commons.

Read more articles from Issue 08: “The Sex Issue.”