On Dating

When I was in middle school I would pray for my first kiss kneeled in the pews of Catholic mass.  God, please let a boy like me so I can get my first kiss. I thought there was something wrong with me when it took until sophomore year of high school for me to finally get that kiss.  It seemed like all my other friends had already reached this monumental landmark.  In high school, I became one of the few people I knew without a significant other—and I’m talking date for 6 months or more and spend almost every waking hour together significant.  At the time, this felt like a choice.  I didn’t want a boyfriend.  I wanted to focus on me.  I cared more about my grades than my relationship status.

Growing up, when family friends came over for dinner or a Christmas party they would always ask if I had a boyfriend.  It seemed that as soon as I entered middle school I was suddenly allowed and expected to like boys in this way.  “The boys must be all over you,” they would all say to me.  “You’re so pretty.”  When I admitted that they weren’t, that I had no boyfriend nor any prospect of one, I questioned whether I was beautiful at all.  Maybe I’m not actually pretty, I’d think.  If I was pretty, the boys would be all over me like our friends said.

Because of those comments said to me growing up, it has taken me years to convince myself that the reason I have never been in a significant relationship is not because of my looks. Like most girls I struggle at times to maintain a positive self-image, but unlike most girls, the times I do feel self-conscious about the way I look are fleeting and rare.  Instead, I tend to believe in my innate beauty.  I am confident about my appearance and my body.  And this has brought conflict.  If I’m so beautiful and confident, why do I not have a boyfriend?

As I entered college, I thought perhaps a relationship would occur naturally.  But while all my friends seemed to pair off, I was still conspicuously single.  When a guy showed interest in me my sophomore year I allowed him to pursue me.  We had a short relationship—4 months.  I lied to myself nearly the entire time that I liked him.  But in reality, I only liked him because he liked me.  I didn’t think of how I wasn’t actually physically attracted to him.

Last year, for the first time, I was motivated to start dating.  No more sitting around and waiting for something to happen, I thought.  I’m going to be proactive about this whole thing.  I got a dating app.  I swiped left and right.  I texted people through the app.  And went on many, many first dates.

I’ve gone to dinner at a restaurant off Colfax where I texted the guy the next morning that I didn’t think we had enough chemistry to go on another date.  He texted back: It seemed awkward to me too, but I just thought that maybe I was a little rusty. He had talked about his border collie for the majority of dinner and laughed at things I couldn’t quite understand.  In short, we had very different senses of humor.  There was another guy that I met for Thai food.  He had on an ironed polo that was buttoned to the very top.  His speech was formal and stiff.  I wanted to leave five minutes after I sat down.  I’ve been on a handful of dates at breweries where it always happens to be trivia night.  I suck at trivia.  We end up trying to answer the questions haphazardly when there is an awkward lull in the conversation.  Another first date was downtown on a weeknight. The guy was very nice, albeit a bit young.  He admitted that he suggested the place because it was close to his school.  He was finishing up his undergrad degree after more than six years of working on it.  That should have been my first clue.  He ordered several rounds of very expensive margaritas and guacamole for the two of us and when the bill came and I offered to split he didn’t hesitate to say yes.  It was the most expensive dinner I’ve ever had.

After a year of dating apps I haven’t gone on anything beyond a third date—and that only happened once. I am still entirely single, which has made me wonder again—is there something wrong with me?

The right person will come along, my mom and many of my friends have told me.  And I still believe them.  But when?  I feel like I am that middle school girl again, praying in a pew for my first kiss, desperate for attention from a boy, as if this will validate who I am as a person.  I am by every means successful—I am in medical school, I live in a beautiful part of the city, I have friends who support me and a family who loves me—and yet I feel that I need to be in a relationship to be whole.  I hate that I feel that.  It goes against everything that I have ever told myself.  Confidence is a choice, my soccer coach in high school always told us.  None of this bullshit of ‘I’ve lost my confidence.’  I wholly believe in that and I like to think that I encompass it in every other aspect of my life.  But dating?  It seems as if I need some external validation in order to be confident about my ability to love a man.

A few weeks ago I was listening to a podcast with Brene Brown where she talks about the power of vulnerability. It felt like it was speaking to me at exactly the right time.  I was trying to convince myself to start dating again after a three-date stint with a guy ended.  I felt incompetent.  Yet again, I had failed to make an actual connection with someone.  Brene Brown argues that vulnerability is the key to human connection.  Maybe, I just need to be more vulnerable, I thought.  The day after I listened to the podcast a friend told me that I came off as slightly guarded.  At first, I was offended.  I’m not guarded.  Quite the opposite.  I told her this.  “Most times I feel that I share too much information with people.”  She nodded and shrugged her shoulders.

As I thought about her comment over the next few days, I realized that there must be a glimmer of truth to it.  I’m not guarded with friends or family, or at least I don’t think I am.  But maybe I am guarded when it comes to dating.  I feel as if I am on watch, observing every move from the guy, slightly suspicious of what will happen next.  With men I’ve never met before, it is always slightly intimidating to immediately enter in to what will ultimately be an intimate relationship.  I am afraid of making the wrong choice.  Or worse of dating a man that will eventually hurt me.  I think of the worst outcome because of my parents’ marriage.  My father had an affair with my mother, which led to a blistering divorce, one that lasted for far too long, my parents going in and out of court fighting over alimony and child support.  My relationship with my father never recovered after that.  To this day I hardly ever talk to him – although I would be open to a relationship if he reached out.

After listening to Brene Brown and talking with my friend, I made a commitment to try and be more vulnerable in my dating life, to be less worried about what will go wrong and lean in to what could go right.  My first test was asking out a friend who I have liked for a while.  Here I was not only putting myself out there but reversing what I had learned my entire life from my mom and her friends – the guy must be the one to ask you on a date.  He stumbled over the phone to answer.  He was taken aback and immediately I began to regret my decision.  But after a few mumblings of how surprised he was and a long pause, he said yes.  I was relieved, although a bit hesitant that any of this would actually pan out.  We went for drinks and dinner the next week and it went really well.  And then our second date went well too.  I was happy.  All I needed to do was be vulnerable, I thought. But there were times too, where I doubted that it was real.  He’s being insincere.  He’s telling me he likes me even though he doesn’t, I thought. Believing that something will go wrong when everything seems to be going right, Brene Brown says, is just another manifestation of our fear of vulnerability.

Unfortunately, my doubts were correct.  Less than two weeks after we had started dating my friend texted me, telling me he needed to talk.  I knew immediately that he was going to end it.  I was devastated. I felt silly for feeling this strongly about him so quickly, for thinking that simply by being vulnerable I had solved all my insecurities about dating.  But the worst part was that I couldn’t even tell my friends that he broke up with me.  We had only been on two dates – so did it even constitute a break up?  In my desperation and lack of experience, our two dates felt like a full-blown year long relationship. But in truth, the whole thing fizzled out before it even began.

In reality, I wasn’t all that upset about the fact that my friend ended it. I’m more in despair because after a year of trying to date, I’ve found that I’ve really only liked him. It scares me that after all those dates I can only say that I was physically and emotionally attracted to the guy that was standing in front of me the whole time and then he couldn’t even return that sentiment.  What does that imply about my ability to create a relationship? The common philosophy is that women find themselves unworthy of love, that they don’t love themselves enough to be in an open and loving relationship. It’s not that I think I’m unworthy of love but that I’m incapable.

A friend in college once accused me of being asexual.  She did so artfully, so that at the time it felt less like an accusation than a thought experiment.  We were playing Hot Seat, a game me and my housemates had come to play every so often.  You chose one person to be in the “hot seat” and then you could ask them any question you wanted.  I dreaded this game because typically the nature of the questions was sexual.  Not being in a relationship previously, I could hardly ever answer with anything scintillating.  “Maybe the reason you’ve never had a boyfriend,” my roommate noted when it was my turn to be in the hot seat, “is because you’re asexual.”

I stared at her.  “Asexual?”

“Yeah,” she nodded, looking towards my other roommates.  “You don’t have a sex drive.”

It was quiet for a second.  I thought about it.  It would explain the reason I never looked at men like my friends did, calculating with one fell swoop his level of attractiveness.  Or for that matter why I didn’t seem to be attracted to men at all in that way, even when I did think about it.

“I . . .well—” I began to protest but I didn’t even know what to really say.

“You’re totally asexual,” she insisted now.  “I mean that’s completely fine.  There’s no reason to be ashamed.”  But the way she said it made me feel that it was exactly why I needed to be ashamed.

I’m sure she has long forgotten this conversation by now, but I have continually replayed it over and over again in my head.  And I can’t help but fear that it’s true.  She had no right to say it, to label me without asking if I wanted to be labeled in the first place.  Yet I can’t erase it for some reason.  In some ways it would be so easy to identify with it.  Yes, I’m asexual and that’s why I’ve found it so hard to connect intimately with others.  But it’s also the last thing in the world I want to be true.

I feel like until I am in a relationship I won’t be able to prove my previous roommate wrong.  And so the threat continues to hang over my head.  Am I asexual?  Or is something else entirely wrong?  Or maybe, just maybe, nothing is wrong at all and it’s like everyone says – I just have to be patient.  The right guy will come along.

God, how I hope that day is soon.

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**Images included below in the off chance you know some single guy you want to hook me up with.  Images selected for their ability to show off my beauty and adventure loving soul.

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