A third date with Анна

Анна was a few minutes late, but I didn’t care. She was wearing comfortable slacks, and an autumnal cardigan over a creamy button down shirt, with a springy hair-tie gathering her long red hair into a tail. The outfit screamed "I love libraries" and made me immediately want to curl around her. Before we went into the restaurant I showed her my cool new folding bike, which she was politely impressed by.

It took a while to go through the menu at Herbivore, but we had an order ready when the waitress finally appeared. For the next ten minutes it was surprisingly difficult to get the conversation going. Eventually we dug into our reading lists, and what books we had "on deck," which did the trick. We didn’t really connect until the conversation turned to dating history, and through that, sex. We seemed to spend a lot of the time talking sex. She was a fellow adult with her own share of adventures, many of which overlapped mine, but sex was curiously unfamiliar territory for her. Actually, it wasn't her lack of experience with it that was curious, it was her intense desire to learn, as though she had taken a sudden interest and was trying to make up for lost time.

She asked me to describe why I liked oral sex so much, and I waxed poetic about it for a good ten minutes, talking mostly about how it made a kind of feedback loop between bodies, and was a sort of miniature journey. “Wow,” she said. “You’re not just a good salesman of computer stuff... You’re a good salesman of anything!”

I laughed, embarrassed. “I swear I’m not trying to sell you on anything; it’s not like that.”

“Oh I know. I’m sorry. I didn’t mean to imply that. It was just...” She giggled - a melodic, staccato rise of notes - and thought for a second. “It was a very good explanation.”

“Well, thank you!” I said.

She talked a little more about her history, picking carefully through it, not because she was trying to conceal anything but because she was applying a very different perspective and needed new words to explain what she saw. It had been years since she'd had a reason to tell these stories. I relaxed into the discussion, slowing down and offering the occasional thought. It seemed like she needed to process a bit, and perhaps to decide how much she truly had changed, ... or intended to change, at least.

When we finished the food we agreed it was far too soon to end the date, so we went for a walk. She took me up onto the Berkeley campus, and eventually led me to a bench, half-hidden in the shadows of a redwood tree next to a building. It was the one she had been looking for two days ago when she suggested that we find a place to make out. Looks like it was time to give that a try.

We sat down awkwardly at first, as though we were strangers in a church. I turned to her and leaned in, and she shifted a bit, giggling nervously. In the back of my head there was some confusion: What sort of sense did it make, that a person 30 years old, looking this gorgeous, had so little experience that she didn't know how to kiss on a bench? And why was she suddenly this keen to try it? Something she's said a few days ago tugged at my mind. Something about a tendency she had to treat new experiences - positive or negative - as grist for her artistic process. Was this all an experiment? If so, who was the subject? Would she abruptly declare it over at some point, and retreat to her books?

I didn't care.

The first kiss was extremely Disney. Our lips touched but almost nothing else. This was hilarious but also deliberate. She was sweating lightly, as though there was suddenly a lot at stake. I didn't want to freak her out. So, next it was a kiss, with one hand on her knee. And so on. Eventually two hands. Her own hands moved around, unsure of where to land.

She complimented me on the way I held her. She paused, seeking words. "It's ... solid. Present." I got a little more elaborate, and drew my hand up from the base of her spine, slowly, palm flat, until it was curved around the back of her neck. “Yeah, like that...” she said.

Things seemed to be going well. I complimented her on her smell, and the softness of her lips. I asked if she wanted some advice on using tongues, and she agreed. She picked it up immediately. Every now and then she'd pull her head back and sweep her eyes around the lawn in front of the bench, obviously paranoid about being observed. Kissing in public, even at night on a bench in the shadows, was a huge transgression back in the religious community where she'd been raised. People kept passing by, but none of them took an interest. I wondered out loud if a park bench was really the best place for this sort of experimentation. She looked a little bit ashamed, and said, "I figured this would be safe enough, but also, I figured this would prevent me from going as far as I might want to otherwise."

I laughed, but made sure it was a kind laugh.

We kissed in waves, talking about philosophy and sexual experience in between. We asked each other increasingly embarrassing questions and giggled a lot. Her enthusiasm was contagious, and we both had goofy grins after a while. It was fun to feel like I was transgressing, even though I knew we were both being very mild by Berkeley standards.

The kissing eventually got passionate. Her hands gained confidence, and began grasping. She was sweating but didn't want to remove her cardigan. She paused, and abruptly confessed that she’d only had sex five times in her life. "I don't mean sex with five people. I mean, five times. That's it. With two people."

Intensely curious, I asked her how it had gone. I was bracing for something negative, since perhaps that would explain why it had been so rare.

"Well, the first time it hurt like hell. That wasn't very fun at all. I got really upset, like, 'what if that's how it always goes for me?' It was kind of ridiculous, and it was a while before I wanted to try again." She continued, telling a story that drew a picture of her younger self, as a person constantly struggling against the idea that sex was a transgression, and so the few times she'd actually engaged with it she was already wound up with intense feelings of defiance, and hyper-aware of every detail, which also prevented her from relaxing. Then the overstimulation would force her to retreat for another long interval. I silently cursed the mechanisms of sexual control baked into her family's religion and the others like it. In an era of birth control and economic options, what was the point of all that psychological damage?

And that thought jumped up again, in the back row of my mind: How much of that is now internalized, as denial for the sake of suffering, for the sake of being "an artist?"

It would weird me out if I thought about it too much, so I didn't. I would rather kiss her, and just see where things went.

"So, really not much experience," she said. "You probably understand why your stories are so interesting to me."

I nodded, and hugged her with my free arm.

She sighed. "You know, I don't even know what positions I like. I've only ever had the chance to try one."

I wondered which one it was, but kept quiet. It suddenly felt impolite to ask.

"Anyway. Um. What were we just doing?" she said, leaning in.

Being fascinated by the inexperience of a partner was a new thing for me. It helped that she was so eager to learn. I couldn't remember the last time I'd been the one teaching someone else.

We kissed for a while longer and talked about fantasies. She told me she had been trying to visualize giving oral sex, but couldn't put the pieces together in her head. I didn't bother replying that she could experiment on me -- that was already obvious. I also knew it would probably take quite a while to work up to that, if we ever did. Kissing continued. Then she suddenly stopped, straightened up, fixed me with a bold expression, and said, "Here's what I want. I want to straddle you. But this park bench is just too exposed."

I grinned at her, but also raised an eyebrow, quietly asking if she was sure. She just smiled back. We schemed a little bit, laughing at the naughtiness of it all, and eventually decided on the large redwood tree behind us. It cast a deeper shadow in the other direction, where it merged with other trees overhanging a small creek. We got up, pointlessly arranged our clothing, then walked hand-in-hand like a couple of storybook characters to the other side of the tree and sat down near it, on the slope facing the darkened ravine with the creek chattering below. I laid back onto the forest floor and she climbed awkwardly on top of me, grabbed my shoulders with both hands, and began kissing me with more intensity than style, and moving her hips. I grabbed onto her butt and pulled it down onto me, through the layers of our pants. She let out pieces of a low moan through the corners of her lips, between kissing. Dimly I wondered if this was the one position she knew, or her first try at something else.

I found the hem of her shirt, which had come untucked, and moved my hands up it, encountering an adorable lace bra with stiff plastic underwire. As my hands moved around she made another sound, much louder, and completely lost her rhythm. A moment later she pulled her feet under her knees and stood up. "Okay, uh, I think I need to stop," she said. "I'm feeling suddenly uncomfortable." She panted for a while, looming awkwardly over me. "I think I may be going a little overboard, uh, at least for tonight."

She arranged her clothing and sat down next to me, knees to one side, and placed one hand on my chest. Her breathing began to even out. "Besides," she said, "we know we're not going all the way so we're really just torturing ourselves, right?"

I got up on my elbows, smiling at her, and said I didn’t feel tortured - that I was having a great time in fact - but I knew what she was trying to say. We didn’t have four walls around us. If we had, we would have probably removed most of our clothing by now, and been coming up with reasons to keep going, rather than stop. With Анна, that would have definitely been too far for the third date. The park bench had been smart.

I stood up and then held out my hand, and she pulled herself up. In a flash I was reminded of how different our forms of self-confidence can take. I had just been on a date with a woman who would have absolutely refused an offered hand, because it would have represented some kind of assumed weakness. For my part, offering a hand was at first something my mother advised me to do, and from then I internalized it as my masculine desire to be useful and helpful and protective. Анна had casually taken the hand without a second thought, and also without a "thank you," because in her background it was so firmly established that a man helps a lady up that it didn't even warrant a show of gratitude. And oddly, I didn't feel like a "thank you" was lacking, because I was playing the complementary role on our date.

A minutes later as we hugged by the bench, she brushed fallen leaves off the back of my shirt, a reciprocated gesture of caring that warmed my heart.

We began walking, my hand clutching hers, her arm tucked behind mine so that the walk was more intimate. As the conversation flowed I mentioned that I was extremely attracted to her, and was pleasantly surprised to hear her say, “as I am to you.” It was the first time she'd made it clear.

We already had another date lined up for the weekend, so there was no need to negotiate. We strolled down to the Bart entrance and paused at the top of the stairs. The parting kiss was warm and lingering. I stood around for a moment, and sure enough, she turned around at the base of the stairs and gave me a shy wave before disappearing around the corner.

I walked back to my bike and was pleased to find it still there. One never knows in Berkeley. During the ride back to the house I tried to check in with myself. Where could this be leading? Where did I want it to lead?

I had other dates lined up in the near future. I figured that if Анна truly knocked my socks off, I would be shying away from those dates, or from scheduling more. But I wasn't quite there. Partly it was the gulf of experience between us. We were taking advantage of that to have fun together now, but it could be a problem later. I chided myself that I wasn't ready for a deep commitment to start, even though I felt the lack of one desperately. I was trying to act ready. I couldn't quite admit that it wasn't working.

The dating site questionnaire asked people right up front: "What's more important to you right now? Commitment, or sex?" I'd automatically chosen "commitment," because that was how I thought I worked. Or, it was how I told myself I worked. But maybe I was wrong. After all, there were dozens of boxes one could try to check when searching for a long-term partner ... but I was spending time with Анна, and the boxes she checked were: "Likes and respects me," "is available," and "wants to make out." The other boxes remained a mystery, and perhaps it was a sign that I was totally okay with that. I just wanted to make out more. As long as Анна did too, I would keep coming back.