Grandma's Got a Boyfriend... and I Don't

“How’s your love life?”

“Not as exciting as yours, Grandma.”

My grandmother is 86 years old and she has a long distance boyfriend. She’s just been telling me about how every night at 8 pm her time and 10 pm his time (she lives in New Mexico, he lives in New Jersey), he calls her and asks, “Ready to pour?”

They drink one gin and tonic and talk for an hour before bed. This happens every night. She tells me that he’s started calling in the mornings too, “Just to say Good Morning.” I ask how they constantly find things to talk about.

“I don’t know, honey, we just do. We talk about politics and the people we used to know. We tell each other about what we did that day.”

I remember that feeling of wanting to tell a partner everything—purposefully remembering things from your day just so you could tell them about it later, every mundane little detail. I had that with Mr. Intimidated, which is how I knew I actually really liked him. Grandma tells me that her boyfriend admitted to making notes throughout his day so he wouldn't forget to tell her things.

“He makes me feel like a girl,” she tells me earnestly. “I never thought I’d feel that way again.”

My grandmother and her boyfriend, Bob, grew up together in the same tiny New Jersey town where he still lives. They knew all the same people, most of whom are now dead. Bob remembers more than she does about their high school days together—he remembers things about my grandmother that she doesn’t remember herself. Like about that time they were playing tennis in gym class and she got a cramp in her leg and had to sit down and the gym teacher came over and asked Bob, “What did you do to her?” Or when she fainted outside the school and knocked down a professor.

Bob remembers these details because he’s been in love with my grandmother for 60 years. My grandfather died three years ago and this man—a widower himself—waited a respectable two years before swooping in on the long lost love of his life. She wasn’t sure at first and she resisted him for several months—I think she felt some moral obligation about being faithful to the memory of my grandfather. But Bob just kept on coming, undeterred by her reticence.

“I feel silly now about resisting him,” she admits.

When Bob came to visit her in Santa Fe several months ago, my grandmother laid down the ground rules: “Hopper seat down” (she calls the toilet a hopper), “you have to help with the cooking, and... NO SEX.” Her boyfriend joked: “If you wanted to have sex, I’d have to bring someone in.” At first I interpreted this to mean a prostitute and I was momentarily shocked. Then my grandmother laughed, apparently charmed by his little joke. I guess he meant a doctor or something. Someone to administer the Viagra? I don’t know.

One of her favorite things about Bob is the fact that he can keep the names of her three daughters straight. The fact that he remembers that her granddaughter lives in Los Angeles.

“He has a good memory and he obviously cares about you,” I say.

I consider telling her about the guy I had been chatting with on OKCupid for a couple weeks who then, a year later when I got back on the site, opened with the same pick up line he’d used on me the first time around. I remembered the line and I remembered him. We had gone so far as to exchange numbers and had texted on a daily basis—we were pretty close to actually meeting in person before it fizzled out. He’d apparently forgotten all these details and was starting from zero with me. I wondered if he still had my number in his phone. I consider telling her about the chef I was chatting with recently and was really excited to meet. We had made a date, he had to cancel at the last minute, he wanted to reschedule. I said okay and then never heard from him again.

When my grandmother asks about my love life, I’m tempted to mention the fact that I recently deleted all my dating apps after reading a particularly depressing article about Tinder in Vanity Fair. Midway through the article, I grabbed my phone and promptly deleted ALL the apps: Tinder, OKC, Hinge, Happn, even Bumble. I decided I didn’t want to feed into this culture that was turning men into sociopathic pussy-monsters and women into simpering attention whores. I decided I would meet someone the old fashioned way: IRL.

I can’t explain any of this to my grandmother because it simply wouldn’t make sense to her. On a fundamental level, her generation doesn’t understand having a game on your phone where you swipe through millions of human faces trying to find someone to have sex with. Her boyfriend has been in love with her for 60 goddamn years! They talk on the phone every night. She’s living in some nostalgic Nora Ephron romance flick from the 90s. Every time she tells me about Bob, I get off the phone and quickly jot down some notes.

“I have to write this story!” I tell myself. It’s too good to be true. This isn’t real life. It’s some relic from a sweet unattainable past.

I remember my grandmother watching this short film I made in which the three young women gather in the kitchen explicitly talking about sex and masturbation. I had been nervous to show it to her, but her reaction was amazing.

“Do you girls really talk like that?” She asked, intrigued.

“Yeah, we do,” I told her.

“That’s really great,” she said to my surprise, “In my day you simply didn’t talk about that stuff.”

I think about the fact that my grandmother has only had sex with one man her entire life. The fact that she got married right out of high school, didn’t go to college, and had three daughters. I think about how she was the star of all her school plays, a real beauty, but didn’t have enough belief in herself or encouragement from her parents to pursue a career in acting. The fact that she is also a poet and a painter, and considers these talents to be just hobbies. And that she never really liked to cook—my grandfather was the one who loved being in the kitchen. My grandmother grew up in a generation where women were expected to stay home and bare children. And that’s it. And I think if my grandmother had been born of my generation, she wouldn’t have chosen that path. She probably would have been an artist. Maybe an actress. She would have had a choice.

When I ask my grandmother if she has any plans to visit Bob in New Jersey, she says she doesn’t have any desire to, that she really doesn’t want to stay with him. She insinuates it’s because she doesn’t want to have sex.

“If I were your age maybe I’d want to visit him…. You can guess what I mean.” She laughs. I laugh too. Last time I saw my grandmother she declared that she’d never have sex again. I just stared at her, mouth dropped open, like ‘how could you ever say that?’ Especially after having had sex with the same man for my entire life, I feel like I’d be chomping at the bit to see what else was out there.

“I just don’t want to anymore,” she said at the time, resigned. I guess it makes sense. Biologically speaking it makes no sense at all for a woman to still want sex at age 86. Still, I can’t imagine myself ever saying the words, I’ll never have sex again. Maybe on my deathbed.

Considering the generation my grandmother grew up in, it’s not totally inconceivable that she never actually enjoyed sex in the first place. It’s even possible she’s never had an orgasm. When I sent her a DVD of the first season of Masters of Sex for her birthday, her response was that she found it “silly to even study these things.” I explained to her that before the studies of Masters and Johnson, female sexuality was cloaked in shame and misunderstanding and that, although imperfect, even just the fact of their study was a step in the right direction. Despite finding it silly, she still said, “I’ll probably watch the rest of the seasons.”

Although I don’t idealize my grandmother’s generation and I certainly wouldn’t want to go back to a time when women had no sexual freedom to speak of, I think something has been lost in this age of endless choice. I’m nostalgic for a time when, if you wanted to talk to the person you had a crush on, you had to call them on the phone or drive to their house. You couldn’t just send them a text or stalk them on Facebook. There was more risk involved, and therefore more investment. You couldn’t swipe through a hundred potential dates a night. You had to talk to one person at a time and risk actually liking that person. Is romance dead? No. But it’s definitely old and potentially dying. 

It's a Match!

I went on two dates last week. With the same guy. They were real dates, not just sex dates. And he planned them, which was awesome. On Monday night we met for drinks at a classy whiskey bar and ended up sharing a pizza. The conversation was varied and flowed easily. He listened intently as I talked, seemingly very interested which inspired me to be even more interesting. At some point, we moved from the bar to the lounging couches in the corner of the restaurant. I started touching the veins on his arms (I love the veins on men’s arms). He smiled and lost his train of thought. We kissed a little bit. He smiled more. It was nice.

We shut down the bar and he walked me to my car. I then drove him the two blocks to his car. I parked and left the engine running, music blaring as we made out furiously. I felt his crotch and he pulled my tit out of my shirt. I could feel he was hard in his pants and I started to unbutton his fly. I pulled out his dick and decided to put my mouth on it right there in the car. What can I say, Florence and the Machine’s Only If For a Night was blasting and I felt inspired.

“Can I invite myself over?” He asked.

He followed me home in his car and we huffed and puffed as we struggled to walk up the incredibly steep hill I live on. When I got him in my bed, we proceeded to continue where we had left off. Only problem was, he was no longer hard.

“Ahh, my dick!” He lamented.

I reassured him it was fine. It happens. He was clearly nervous around me. We had talked earlier in the evening about the phenomenon of emasculation.

“Do you feel emasculated by me?” I asked now.

“Sort of,” he admitted.

“Why?”

“You’re just such a sexy woman,” he declared, grabbing my ass.

Obviously, this was the right thing to say. I was flattered. But I also wondered why this keeps happening to me—the fact that my being a sexy/strong/ambitious woman actually makes guys lose their erections. This has happened before. With men that were apparently really into me, and then when push came to shove, they had trouble performing and claimed to be “intimidated.” 

I pulled out some tried and true sex-ninja moves and managed to successfully get him hard. We had sex and we both came, and I felt more satisfied than 90% of the time when I first sleep with someone new. But he obviously felt embarrassed and frustrated and in his head about the penis thing, and I couldn’t get him out of it. We fell asleep and in the morning we talked in bed for awhile. He shared that he had recently stopped watching porn because it was fucking with his self-esteem (you know, the big dick factor).
"Porn is ruining men for real sex!" I declared, vindicated.
It was nice to lounge in bed with someone—it had been awhile for me. I made us eggs and coffee and we had more good conversation over breakfast. All in all, it was a lovely 14 hour date.

On Thursday, he asked me out again. He picked me up, which impressed the hell out of me (it doesn’t take much) and we went for a couple drinks and then to see a late night showing of It Follows. After the movie, he drove me home. And then it suddenly felt awkward, as if the ghost of last night’s sex loomed over us. As if there were some weird expectation on us now—we’d already had sex, so we should probably do that again. But he was still in his head about how from his perspective it had not gone very well. I leaned over to kiss him goodnight. He kept his lips pursed tightly shut.

The next day, via text, I brought up the awkwardness I had felt at the end of our date and he was very forthcoming about the fact that he’s been "going through some stuff" and that he just came out of this relationship that left him feeling less than confident about his manhood. He expressed his hope that this wasn't "TMI." I reassured him that, in my book, there is no such thing as TMI. I appreciated his vulnerability in telling me the truth. It was a welcome reprieve from the posturing I usually encounter from insecure men who, instead of admitting their insecurities, overcompensate with this big macho act that is really off-putting and I can completely see through anyway.

I talked to my Best Guy Friend about this. About the fact that I actually really like this guy. I like spending time with him, I love our conversations, I like myself when I'm around him, and I appreciate his candor and transparency. But if I'm being honest, this is not the person I see myself dating. I have had this fantasy of dating someone as ambitious and driven as me, possibly more successful/farther along in their life and career. Best Guy Friend has had a similar vision for himself. We’re both looking for the opposite-gender equivalent of ourselves. But I don’t know if that’s possible—I don’t know if that would truly be a match. Maybe every relationship needs that yin and yang, perhaps both partners can’t be equally ambitious because that would never work, maybe we both need to accept the fact that we are destined to be the more powerful partner in the relationship, that we will perpetually be in the driver’s seat calling all the shots.

If I’m honest with myself, I say I want a partner who makes decisions so I don’t have to, but the truth is I actually enjoy calling the shots. In every aspect of my life, I am in control, and I like it that way. This comes naturally to me. I’ve been looking for a dominant, but maybe I am the dominant. I don’t know if I could actually let someone else be dominant over me.

I’ve always had this fantasy that with the perfect match, we’d have like this mutual admiration society. But maybe admiration flows more naturally one way or another. I have to say, I love to be admired and appreciated. My favorite interactions with men are the ones where they want to hear a lot about what I’m doing and think it’s really cool and interesting. My least favorite interactions are the ones where they show off and talk about themselves the whole time and learn nothing about me. Maybe it’s not meant to be equal. Does my preference for being admired point to the fact that I’m naturally dominant?

I think of my mom. My mom is very ambitious and strong and opinionated, she is a leader and a control-freak. Like me. And she married my dad, who is much softer—he acquiesces, he takes her side, he is her support system. And although when she’s frustrated with him, she likes to complain that she wishes she were with someone more ambitious, driven, “successful,” I don’t think she would actually be a match with that person. And I don’t think that guy would put up with her shit. I mean that endearingly—I don’t know if that ideal mate I envision for myself would put up with my shit either. My parents probably have the best example of a marriage I have witnessed, and they’ve been together over thirty years.

Best Guy Friend and I came to the conclusion that maybe the reason we’re looking for that support system in a partner is because we don’t feel 100% confident in our own ability to support ourselves. And once we truly find a sense of security within ourselves, we’ll let go of needing it from another person.

In my new favorite (and now cancelled) show, Looking, there is this great storyline in which the main character Patrick, an upper-middle class, college educated white boy, starts to fall in love with a lower class, Hispanic hair dresser, Ricky. And he feels really conflicted about it—he did not imagine himself with this person. And he can’t deal with it. He ends up cutting it off before it can go too far. And then throughout the rest of the season, the what-if of what that could’ve been hangs over his head. Every time he sees Ricky with his new boyfriend, there’s this sense of that could’ve been me.

I relate so profoundly to Patrick’s conflicted emotions about Ricky. Because this might have been a true love-match for him, and indeed it sure felt that way. But Patrick’s idea about the kind of guy he should be with came along and sabotaged any potential future he might have had with this person he could’ve loved. I feel this level of conflicted about most of the men I have chemistry with—they’re actors and bartenders and waiters, and they’re hot and they like me and there’s an obvious attraction. And whereas when I was younger I would have pursued it at least just for the sex, now I find myself looking into the future. Do I really want to be in a relationship with another struggling actor? Not really, no. But why do I keep attracting them? Why do I never seem to attract that incredibly successful, powerful “man of my dreams”? Am I destined to be that person in my relationship? Should I just relax into that role and embrace it rather than constantly holding out for this imaginary powerhouse I have yet to meet? This person that supposedly “matches me.”

I guess this is my fundamental issue with online dating. Because online dating is all about being good on paper. And it doesn’t account for chemistry. When I think about my ex-boyfriend, whom I was with for four years, if I had seen him on an online dating site, I probably would have dismissed him. Because on paper, we are not a match. But in life, we were. It ran its course, we’re not life partners, but my relationship with him was wonderful and I don’t regret a moment of it. As much as I like to think I want to be with the male equivalent of myself, I probably would find that person completely impossible to be around. My first boyfriend was very similar to me—intellectual, ambitious, Type A—and we fought all the fucking time. I ended up hating him in the end. So I guess in conclusion I’m going to try to keep an open mind—to not be so quick to write people off because I don’t think we’re a “match”. Because you never know. My true love match might turn out to be the opposite of what I expect.

The Pussy Knows

He shows up to Urth Cafe an hour late wearing a shirt that says THE PUSSY KNOWS. I can smell his breath from across the table—hot and musty—and his shirt is damp when we hug.

“I’ve got so much energy flowing through me right now.”

He has just come from a seminar on the female orgasm. On his OKCupid profile, he is a self-proclaimed “female orgasm expert.” Obviously, this is why I’m here.

We talk about Law of Attraction (which he doesn’t believe in), and about how people are much more intuitive than they realize (which we agree on). To demonstrate this principle, when the food runner comes to our table carrying a slice of coconut custard pie and a turkey burger, my date insists he guess which belongs to whom.

“Come on, man, you know the answer.”

The food runner looks flustered and continues to repeat the names of the items, as if we haven’t heard.

Eventually, Orgasm Man gives up and sighs, “the pie is for her.”

I eat my pie with gusto, and he smiles at me, "You have a healthy sense of your own appetite."
"I love food!" I exclaim.
"Not just with eating," he says with a suggestive wink.

Later, he puts his hand on the table between us and I know I’m supposed to put my hand on his. I do, feeling the sweat gather in my palm. He stares into my eyes and we don’t say anything for awhile. Then, he smiles.

“I felt that. That wave you just sent through my body. I can feel it at the base of my cock.”

My mouth twitches into a snicker, but I choose to stay in the game. Also, I’m intrigued. In his very first message to me on OKCupid, he had said, “I find myself standing amongst a ton of people stroking pussy and for some reason in this moment I want to say hi.” I wondered if this was a metaphor—turns out it wasn’t, he actually teaches workshops in which men and women couple off and the man spends fifteen minutes stroking the woman's pussy. So, I knew what I was getting into with this guy, and it doesn’t particularly surprise me when he starts talking about the sensations he's feeling in his cock. However, I do get a hell of a kick out of the fact that this is happening over coffee at Urth Café.

I have to say, I don’t feel much sexual chemistry with this guy. It’s not that he’s not attractive, it’s just that by talking a lot about sex and what’s going on with his cock, the whole sexy game is demystified in an unsexy way. However, I am convinced that this Female Orgasm Expert has to be dynamite in bed. I don’t think that’s an unfair assumption.

At some point, after another long bout of staring into each other’s eyes, he asks, “Do you want to make out?”

I say, “Sure. In the Coffee Shop?”

“No,” he smiles.

And so we leave.

He walks me to my car and then we stand facing each other and, in slow motion, move closer and closer until our noses are touching. Then we slowly bring our mouths and tongues together, and he starts moaning, apparently very into it. I have to say, I am still more amused than turned on.

“Do you want to have sex?” he asks, matter-of-fact.

“Sure,” I say. Despite my incredible lack of horniness, I feel like turning down sex with the orgasm expert is not a smart move.

Then we start to work out logistics. I live East Side, he lives West Side, we met in the middle. I also have an important meeting the next day, and do not want to stay up all night fucking.

“Couple things. I have my period--“

“Don’t care.”

“And I have a big meeting tomorrow so I need to go to sleep soon.”

“I come custom,” he says. “Whatever you want, we’ll do it. I can come over, fuck you for 20 minutes and leave. You can come over and spend the night, or not. Whatever you want. What do you want?”

To be honest, if I listen to my instinct, I want to go home. Alone. I want to crawl into bed and get lots of sleep. But I feel like I have already agreed to the sex and I should probably follow through on that.

“Let’s fuck in the car,” I say.

“I knew you were going to say that,” says the Psychic Orgasm Expert.

We walk to his car, actually his roommate’s SUV he has borrowed for the night. He’s parked on a residential street that’s very well-lit and there are several people milling about. He clears out the trunk, puts down the back seats, makes a pretty functional bed. At this point, logistics are overwhelming passion and I try to think of how I’m going to get myself more in the mood. I pull out my tampon and, with no trash in sight, deposit it in a Recycling bin.

“Sorry, Recycling,” I say.

We then decide to move the car so we get back inside and drive around, looking for a darker, less inhabited spot. We park and crawl into the back.

He pulls off all his clothes, saying, “No time for the sexy undressing of each other.”

I’m wearing a dress so I leave it on. He doesn’t have a condom, but fortunately I do. He puts it on, gets on top of me, and pulls a boob out of my dress.

“You’ve got great tits.”

He plays with them a little, but then immediately starts to push his erection into me. I shift slightly, trying to accommodate him.

“Relax,” he says. So I just lay there while he sticks it in dry, feeling a little sore from the lack of a warm up act.

Then he fucks me for like fifteen minutes. At some point, he says, “This is the point where I would usually ask if you want to get on top.”

We just keep on doing what we’re doing. Every time I try to adjust myself to get into a position where I might possibly come, he tells me to “just relax.”

After a little while, he says, “I’m going to come inside you.” And then he does.

He lies on top of me for a bit, then rolls over, and starts getting dressed.

“That was awesome,” he exclaims.

I just lie there in the dark, thinking ‘that was it?’

He massages my legs for a couple minutes, and then it’s time to go.

For all those pussy-stroking workshops, he doesn’t stroke my pussy at all. Not even for a second.

He drives me back to my car and invites me to a workshop he’s teaching on Monday near where I live.

“I think I have something on my calendar for that day.”

I drive home, feeling a little grossed out. I don’t usually fuck strangers in cars, but the goddamn Female Orgasm Expert? I feel like I’ve been scammed. I look him up online and he is who he says he is—he’s a partner in an organization that specializes in female orgasm. He has youtube videos talking about it, he’s legit. People pay him to teach them how to give a woman pleasure—what? Then I get a little sad for the state of affairs between men and women—if this guy has no fucking idea about female orgasms, it doesn’t leave much hope for the rest of them.

That was Thursday. This is Friday.

I feel I can’t write too much about my second OKCupid date because, in my drunkenness, I accidentally told him about my blog, and I make it a rule not to write about anybody that might potentially read this. 

HOWEVER, there are some details that simply cannot be left unwritten.

My second OKCupid date is with a short Jewish man. I’ve been messaging with this person on and off for like six months. Early on, in reaction to something he said, I jokingly responded, “I don’t think this is going to work.” He countered with, “Well, it was worth a shot. I guess we should part with as much dignity as possible. So, uh… Nice rack.” Not gonna lie, his bluntness/ rudeness had kind of turned me on, and I decided to objectify him back: “And you look like the porn star James Deen, so I’ll enjoy that later…” Which was actually true, he did remind me of James Deen, which was 90% of the appeal. Then he said, “Yeah, I get that… a lot. Though more in person. Take that how you will. Or take that how you’d prefer. But, you know, take it.” This had my triangle throbbing a little, and again I was intrigued. Then I asked, “So you look like James Deen, but do you fuck like James Deen?” To which, he essentially said yes. As with Orgasm Man, this seemed an opportunity too good to pass up.

Turns out, he looks less like James Deen in person. We meet at what he calls a “dive bar” and to me looks like a nicely-lit Chinese restaurant. He’s nicer in person than his snarky online personality. And he’s clearly nervous, laughing a lot and too loudly. As the drinks flow, the snarkiness reemerges and he starts giving me sideways glances and kind of talking down to me. His condescension is annoying but also annoyingly sexy. We move closer and closer as the night progresses, and eventually we start making out in the bar.

His place is walking distance, so we head out at 2am, stopping at a 7 Eleven on the way so he can buy a cheap bottle of red wine. I comment that this particular 7 Eleven is the “crackiest” one I’ve ever been too. Which is true, and I’ve been to lots of 7 Elevens in my day. He then comments that I’m the “whitest” person he’s ever met. I notice that he has a bit of a thing about whiteness, because he was born in the Ukraine and grew up in a very white suburban town on the East Coast, where he was the “most ethnic” kid in school. He still looks pretty white to me.

He tells me that there are two Korean guys living in his apartment—his landlord apparently rented to them without asking him, and they don’t speak English or talk to him at all.

“I’m going to make friends with them,” I exclaim, drunkenly.

“You’re like the biggest seven year old in the world,” he tells me, not for the first or last time that night. I find it hilarious every time he says it.

We don’t see any Koreans when we arrive at his place, but there’s a curtain in the corner of the apartment, and I guess they’re living behind it. We beeline for his bedroom, where we make out on the couch and he pulls off my clothes.

“You look good naked,” he says.

He moves us to the bed, and we have sex. It’s actually pretty hot—he’s aggressive and passionate. At one point, he sucks too hard on my tongue and I groan and push him away. “Aw,” he teases, condescendingly.

After we have sex, I’m sprawled out naked on his bed. He points at my crotch.

“This is unusual,” he says. I look down. Everything looks in order to me.

“This landing strip. I haven’t seen a girl with pubic hair in years.”

Truth be told, I have very little pubic hair, and I’m surprised he’s pointing it out.

“I guess it depends on the kind of girls you’re fucking,” I say.

“Not necessarily. A girl could be a saint and she still would have shaved pubes.”

What?

“It has nothing to do with sainthood, it’s cultural,” I respond. “Does it bother you?”

“No, I don’t mind. I’m just not big on hair.”

I wish I could show you a photo of this guy naked and how completely COVERED IN HAIR he is. I’m surprised that someone this hairy has the audacity to point out the like square inch of hair on my entire body.

“I don’t usually date white girls,” he says. Here we go again with the ethnic profiling. “At least not ones as All-American looking as you.”

“Really? I don’t think of myself as All-American looking.”

There’s that sideways glance again. “You look like a cheerleader. Were you a cheerleader in high school?”

If I had liquid in my mouth, I would do a spit take.

“I was a theatre nerd!” But thanks for not listening to a goddamn word I've said all night. 

He suddenly seems annoyed with me, as if now that he’s come, he realizes he’s fucked an “All-American white cheerleader girl” and feels bad about it, or something. I don’t know. I get up to leave.

“Where are you going?”

“You seem annoyed or something. I think I’m gonna go home.”

“Come here,” he extends his arms. I pull on my pants.

He grabs me and pulls me down on the bed. Takes off my pants. And fucks me again.

I don’t come, he doesn’t seem to care. I head for the bathroom, naked, and I can hear someone in there running the faucet. I guess the Koreans are home.

At 4am, I walk the five blocks or so back to my car, and I wonder if I should have stood up for myself more. If I owe it to the next woman who sleeps with this guy to tell him he has no right to judge anything on my body—I have a banging body and he’s a short hairy little man. I wonder, like I always do after an orgasm-free One Night Stand, if I’m supposed to point out to these dudes that I didn’t come, and that they might try harder next time. Or at all. Or if I should wait to be asked. Orgasm Man didn’t ask me if the sex was great, he thought it was "awesome". I like to think if he had asked, I would have told him. I want to think I’m a good communicator in the bedroom, but I think I’m learning that guys really have no fucking idea and they need to be hit over the head with the cold hard facts. Even the ones who claim to be Orgasm Experts or say they fuck like James Deen. Perhaps they set the bar too high for themselves, and then pussy out and decide not to even try, because they know they can’t live up to the expectations they’ve built. Why would they do this? And why do I continue to fall for it?

The little Jewish Man’s follow up later that night: “You know, all in all, that wasn’t a bad date. Or maybe it’s just been a while for me.” I’m not sure how to respond to this.
“I’ll choose to take that as a compliment,” I say.

Man Child

The second I arrive at his house, I know I don’t want to be there. He looks flustered as he opens the door – wearing a ratty old T-shirt and a disturbed expression, he explains that there is a giant green beetle in his bathroom.

“I showered but I couldn’t put on hair gel for you because the bug was in there making a terrible noise.”

I calmly kiss him and go to investigate. As I look around the bathroom, he plays it off like he thought I would be scared and that’s why he freaked out over this thing, which turns out isn’t that big. 

I have been fucking this guy on the semi-regular for two weeks. I met him at a comedy club where he was MCing and my brilliant comedian friend Lucy was performing. I found him funny and cute, and had asked Lucy about him after the show. She warned me to stay away – she didn’t really have a specific reason, but Lucy is very intuitive and she seemed to be getting a vibe that he was not someone I should mess around with. I believe she used the expression “He likes to fuck 19 year olds from the Inland Empire.”  However, when he asked her for my number, she said she didn’t wish to stand in the way of “young love.”

He texted and said he wanted to take me out to dinner, which I thought was classy – a lot of guys these days seem to feel buying a girl dinner is a little too much effort to get in her pants. He asked what I like to eat. I said anything. He asked what I was in the mood for. I said anything, pick a place, I’ll meet you there. He then suggested we meet at the Sherman Oaks Galleria mall so we’d have options and he wouldn’t have to “drag [me] somewhere [I] won’t like.” Now, this put me off. I’m not in high school and I don’t want to eat dinner at the mall. I was feeling a scratch in my throat anyway, so I cancelled the date. Thinking that was it, I’d probably never see him again.

The next night, after spending all day in bed, I decided I could use some soup… and some company. I texted to see if he wanted to meet me for a very “mellow date.” He agreed, and I appreciated that he was willing to come out for a date that would inevitably lead nowhere. I liked him more than I thought I would. We talked and laughed and made plans to see each other again.

Our next date was at a hole in the wall sushi restaurant. While he ate his rolls without soy sauce, I drank sake and did oyster shooters. I asked how old he was. He made me guess. I guessed 32. “Close,” he said, but wouldn’t tell me more. We decided to go buy two pints of Ben & Jerry’s Half Baked, get stoned, and watch the Amy Schumer Special.

I found his life pretty together for the 32 year old I believed him to be. He made enough money that he wouldn’t bat an eye at taking me out to dinner to a nice Japanese restaurant. And he lived alone in a one bedroom house that, although he seemed embarrassed about how messy it was, really wasn’t that bad. He didn’t have roommates, but lived with an insanely cute Siamese cat with a face that appeared upside down. And his couch reclined at the push of a button.

That night, we had sex, and it was pretty great. He ate me up with gusto, enjoying every inch of my body, which I loved. I found him a little paunchy, but in the dark it was no big deal. I enjoyed kissing him. The sex was awesome. And, especially, he was amazing at eating pussy. The only issue was one I come across often with dudes – he was resistant to using condoms. Eventually, I stopped enforcing them so we stopped using them. After we had sex, he asked if I was on birth control. I joked that it was proven less effective when asked after the fact. When he asked if I had herpes, I said “not yet,” which apparently didn’t amuse him.

Then he got a little pissy and complained that I was trying to have sex again too soon after the first go round, that he wasn’t really ready, and wouldn’t have been able to stay hard had we tried to use a condom.

I felt like he was blaming me for the lack of condom use even though I had tried to enforce them, albeit lamely. I told him so, while getting dressed in a hurry.

“Why didn’t you tell me if you didn’t want to have sex again,” I asked.

“I didn’t want to appear unmanly,” he said.

He grabbed my arm.

“By the way, I’m 43.”

I Ubered home.

Later, in my own bed, I felt remorseful. I liked fucking this guy and hated the idea that I was incapable of having successful casual sex. I decided to parlay the situation into a purely sex thing. Skip dinner, get right to fucking. The less talk, the better.

Our next couple encounters were great. We’d get stoned, eat ice cream, and fuck. He was amazing at eating pussy and he made me come hard. I didn’t love his personality – I found him slightly whiny and could foresee the age difference becoming an issue – but I was able to look past these details in order to have some really great sex.

Until this one particular night. The night of the bug in his bathroom. I had been on the fence about coming over, but he kept sending me sexy texts and my best guy friend encouraged me to “go get laid.”

When I arrive, it’s already 11:30 on a work night so I figure we’ll get right to the fucking. I immediately find myself not that interested in kissing him, which is never a good sign, but as he grabs my ass and nibbles my neck, I give in to the sensations.  He starts eating me out from behind which turns me on a lot so I tell him to “fuck me.” Instead, he scoots me around so I can suck on him. I manage to get him fairly hard and he crawls on top of me – we start having sex. I can feel him gradually losing his erection with each thrust. Eventually, he stops and tries to pull me up.

“What do you want me to do?” I ask.

“Touch me,” he says.

So I do, but he’s so soft I begin to lose faith.

“Are you okay?”

He stops and lies down next to me,

“I just feel like we’re not connecting like we usually do. I feel like you’re not even looking at me.”

I laugh, uncomfortable.

“I feel like you’re blaming me for the fact that you’re not hard,” I say.

“Well…” he says.

He’s right of course. I wasn’t looking at him, wasn’t really kissing him, was actually discovering in that moment that I wasn’t that into him. But I thought guys could look past these details when it came to sex.

I explained that sex doesn’t always have to be super intimate, looking into each other’s eyes and all that. That sometimes it’s just about physicality and enjoying the sensations. He said he felt like I was “the dude” and he was “the girl” in the situation.

He complained that this time there hadn’t been much foreplay. That he had eaten me out from behind and immediately I had told him to “fuck me.”  This was confusing because I was simply taking his lead – in one of my favorite sexy texts from earlier, he had said he wanted to “eat [my] pussy from behind, then fuck [me].”

“Every time you leave I feel like I’m never gonna see you again,” he says.

I decide to get real.

“Maybe this thing has just run its course.”

He looks surprised by this. I explain that I loved the sex with him, that it was some of the best I’d ever had, but that if the sexual connection was lost between us, I didn’t see what remained. He says he feels like I turned this into a “sex thing” when he actually really liked me, felt we had a good connection. Really? I want to ask.

Then he starts telling me about this crazy girl he used to date who had to go to love addiction therapy, whom he hasn’t seen in eight months, and whom he feels he’s still in love with. Huh? Then he tells me about this 24 year old he’s talking to on OK Cupid, but assures me he would never date a 24 year old unless she was “really mature.”

At which point, I ask the question that’s been bugging me ever since he told me he was 43 years old.

“Why is your age range preference on OKCupid 25-39? Why aren’t you interested in dating women your own age?”

He tells me, with a straight face, that if he married a 40 year old woman, she would be 50 in 10 years and he wants a wife that’s “hot for at least a decade.” I inform him that he too will be 50 in 10 years – in fact, he’ll be over 50.

To this he replies, “I’m just being honest. Men care more about appearance.” I don’t know what disturbs me more, the fact that he wants the woman he’s with to be 10 years younger than him, or that he thinks women over 50 aren’t hot. 

I’m actually pretty sure I know why Comedian Guy dates younger women, and it’s not just because he’s a shallow asshole. It’s also because there’s no way a woman in her 40s is going to date a 43 year old Man Child who works part time in a real estate office, does stand up on the weekends, and lives in the valley with his cat.  I mean, I’m barely putting up with this situation and I’m not even 30.

So, what kept me coming back? Honestly, the pussy-eating.  And I have a theory about this. If a man is over 40 and he hasn’t been married yet, he’s getting fucking desperate. He’s not going to get a woman with his moobs or his lack of a substantial career. He’s going to win her over with his ability to eat pussy. Because guys in their 20s, you might as well not even let them go down there. And guys in their 30s are still way too selfish to put in the work that’s required. It takes the patience and desperation of a man in his 40s to really nail it, so to speak.

As a form of goodbye, I tell him I feel we’re at different stages in our lives.  When I thought he was in his 30s, his shit seemed pretty together. At 43, there are some expectations for where one will be in their life. I’ve noticed that a lot of my friends in their late 20s are finding themselves at a crossroads where they’re having to choose to commit to one aspect of their life over another. It’s like up to this point, we’ve all planted a bunch of seeds that have been gestating and have finally started to grow. And maybe one plant is doing better than another, and we literally don’t have enough energy to keep more than one plant alive. So the time comes to commit to one and really grow the shit out of it.  I see this a lot with my female friends. I had a friend recently give up her dream of becoming an artist and now she’s engaged to her boyfriend– with her dream career out of the picture, she has chosen to really commit to her relationship. Certain friends are getting married and even starting to have babies, and then there are the single friends who are choosing to commit to themselves and their careers, and finding they’re finally having some success.

So, I guess I feel like, if you’re 43, at least one aspect of your life should be pretty awesome. If you’ve been tending a relationship, or a career, or anything, for a decade, shouldn’t you have something to show for it? Pussy-eating abilities aside, I guess I expect more from a guy who’s 43 – I expect he’ll have his shit together more than the 27 year old he’s fucking.