Sexpectations

I’ve been seeing someone. Just three dates, but it’s felt more real than any “relationship” I’ve had in quite awhile. On the first date, we met at a nice wine bar and had charcuterie, and he didn’t even try to kiss me. On the second date, dinner of oysters and a whole fish followed by dancing, all of it planned and paid for by him. We went back to his place and it was late so we both decided I would sleep over. I think neither of us wanted to necessarily have sex yet—we wanted to take our time—but seeing as I was in his bed, how was that not going to happen? We had sex and it was nice, and then the next morning (Valentine's Day!), we had sex again, and we both came. (You guys, I had an orgasm on fucking Valentine's Day!!) On the third date, he took me to a self-realization center and then we went to my favorite restaurant for dinner. Again, he paid. This time, he picked me up and brought me a tiny vase of handpicked flowers. All of this I found incredibly romantic and unexpected.

Something happened after we had sex. Something that frequently happens. I found myself thinking about him more than I had before. Missing him, wanting to see him again. My female brain had turned on. Whereas before I had felt casual about our dates, now I felt anxious about the next one and like I was counting down the days. What was happening to me? It was all the scarier because I felt I really connected with this guy and didn’t want to fuck it up by getting obsessed.

Let me back it up. A month ago, I went on an ayahuasca journey. I drank the tea and lay down for a six hour, closed-eye meditation, and let's just say I saw some stuff. I saw John the bartender and all the various guys I'd had sex with over the past three years and, in a sudden moment of clarity, realized that what I had been searching for outside of myself had actually been within me all along. I was filled with an intense feeling of being in love that had nothing whatsoever to do with any of these men—in fact, it was a feeling I had never quite achieved with any of them. I felt in love with myself. I know this sounds very new age-y and some of you might be getting ready to barf, but it was a big revelation for me and afterwards I felt truly invigorated. I realized I was happy being on my own, knowing that I didn’t need anyone else to make me feel good or fulfilled.

Then this guy came along. And he really took me by surprise. We had met at a place where he works and I was freelancing, and then ran into one another around the reservoir by my house—him jogging, me walking. He said we should get a drink sometime. I said yes, enjoying the possibility but also thinking it might never actually happen, and continued on my walk. Within the hour I had a text from him saying he had gotten my number from a coworker, he hoped that was okay, and how about tonight?

At the wine bar, I found myself telling him everything, even about my blog—a subject I’ve made it a rule never to discuss on a first date. I can’t explain it except to say that from the questions he asked, I couldn’t not talk about the real stuff that was going on with me. I told him about my ayahuasca journey, about my revelation that I am enough. There was no small talk. I told him about my three years of sluttery and how I felt them coming to an end, that I’d recently had an epiphany that I wanted more than just random sex with strangers. He enjoyed my candor and shared that he too had been slutting around since his fiancé basically left him at the altar, and that he was also coming to the end of this period in his life. I was surprised at how easy it was to talk to him. I had been nervous about the date, in part because I wasn’t sure if we’d have sexual chemistry, and also because I was pretty out of practice at the whole dating game. On our third date, I explained to him, “I don’t date much. I have sex and long relationships.” He told me I should go on more dates. 

What I liked most about this guy was the lack of games. After our first date, he texted that he was “still smiling” and wanted to see me again. Even when I went on my angry feminist rants, he seemed to gaze at me fondly. As we lay on the grass at the self-realization center, he watched me watching a couple young kids playing and said, “children laughing is the best sound in the world.” He seemed to be waiting for a response. What was I supposed to say to that? When a man says something like this, the woman swoons; but if a woman pays too much attention to babies on an early date, the man is likely to run for the hills. It reminded me of that Sex and the City episode when Carrie, trying to get back together with Aidan, goes to his apartment in the middle of the night and throws rocks at his bedroom window. In voice over she says, “When men attempt bold moves, generally it’s considered romantic. When women do it, it’s often considered desperate or psychotic.”

This guy told me that he had talked about me with his best girl friends, and that he'd just bought a sail boat and that “we should sail to Hawaii!” Maybe it’s just me, but when someone says something like this out loud, I take them seriously. I don’t assume this is just something they might say to anyone who happened to be sitting nearby. But maybe I was wrong. Maybe this guy does act like this with every girl he meets—stares fondly into her eyes, makes her feel like he’s falling for her—when really he’s just equally interested in all humans. He told me on our second date that he felt that sex was a contract and that he was more careful with it now because he knew that women could get hurt. He said he had tried to have casual sexual relationships with women and it never worked out for this reason.

When he dropped me off that third night, a Saturday, we made out furiously outside my front door. He was ending the night prematurely because he had to get up very early the next morning to help his friend build a deck before a baby shower and, as he explained, he liked me and wanted to get to know me better. Meaning, I guess, he didn’t just want this to be a sex thing. That honestly didn’t occur to me, as I found myself much more drawn to his personality and our emotional chemistry than the physical aspect of our connection. To me, the physical was just an extension of how we were connecting on so many other levels. He told me, "what I'm looking for is a best friend who also makes me really horny." Aren't we all, I thought.

He asked if I wanted to see a movie the following Wednesday and I said yes. I had already invited him to a concert on Friday, so now we had two dates for the coming week. My roommates were out of town and I had said he should come over and I’d make him dinner—he suggested we do this on Friday before the concert. I warned him that we shouldn’t make too many plans, but I found myself wanting to make more plans with him, even thinking about distant future plans that I really shouldn’t have been thinking about. Excited, I started to design the menu for Friday night.

On Tuesday night, he called to say he probably couldn’t do a movie on Wednesday after all because his work week had gotten insane. I put a smile in my voice and said, “Sure! No problem! What about Friday?”

He hesitated, “Well, the thing is we’ll probably be shooting all day Friday into the evening… but I might be able to make it.”

“I don’t want to stress you out!” I yelled happily into the phone.

“You’re not! It’s stressing me out that I can’t see you.”

“No problem!”

“Why are you so cool?” He asked, a delighted tone in his voice. My face reddened, thinking of the Amy Schumer sketch about the “Cool Girl.” I’m not, I thought. I just didn’t know I was allowed to not be cool in this instance. After all, we’re just casually dating.

“Well, if you can’t make it Friday, please just give me some notice so I can find someone else to go with me,” I said. He promised he’d let me know tomorrow. We hung up, and I was irrationally flooded with disappointment. I almost burst into tears. What was wrong with me? What did I expect? Why had I built this into some big thing? Here we had made two dates this week, and he had essentially cancelled both of them. But why did I care so much? How could he have known that I already had a full menu planned for Friday night? I felt emotionally raw and out of control. I didn’t like this feeling. I was having PTSD from the time when Mr. Intimidated told me at the last minute that he couldn’t come to the Sleater Kinney concert with me, and I couldn’t find anyone else to use the ticket, so I ended up going alone. I wasn’t going to let that happen again. I decided to preempt the situation. I invited another friend whom I hadn’t seen in awhile to come with me to the concert. He said yes. I felt better, gaining back some sense of control.

When I told the guy that he was off the hook for Friday, I expected him to say something like, “Bummer! I wanted to see you.” Instead, he said, “Haha! Okay!” I suddenly realized that, despite the intimate behavior and loving way he looked into my eyes, he actually did feel pretty casual about this. Maybe all men felt casual about everything all the time. I was apparently incapable of feeling casual about any guy I fucked. And here he was, apparently not really caring that he would now not see me for over a week. I suddenly realized I wanted even more than this. Even more than a man who would bring me flowers and plan interesting dates, I wanted someone who showed up when he said he'd show up and who understood that I’m a planner and when I plan something and someone throws a wrench in my plan, it stresses me out. Maybe he doesn’t know this about me yet, maybe he won’t like me anymore when he realizes I’m not as cool as he thought, but that’s a risk I’ll have to take. I can be the Cool Girl a lot of the time, but not all the time. And I need to be with someone who doesn’t require that of me.

I don’t know what the future of it is. We’ll probably see each other again—after all, we do have tickets to attend Dan Savage’s amateur porn festival Hump! when it comes to LA in March so, unless something comes up and he has to bail, we’ll probably still go to that.

I find myself very vulnerable lately, and also full of expectation. There is so much I want and I really can’t let the whims of a man control my emotional state—it happens too easily of late. I know I’ve said before that I should stop having casual sex but I think I need to take it a step further and instigate a three dates before sex rule of thumb. The culture tells us that sex is casual and no big deal, and even I have spouted this same logic on this very blog. But I think I was underestimating the power of sex, the power it has over me. I have taken it too lightly, and it's not fun anymore. It's been a learning curve for me to even realize that by saying this, I'm not slut shaming myself, but actually protecting my heart. No matter how casual and cool I try to act, I can’t deny the effect that sex has on my emotions and my general sense of well-being, not to mention my ability to focus. I think men don’t really understand just how hurt we can get. Because we’re literally letting them inside our bodies. They don’t know what it’s like to be that vulnerable.

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.