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.