Cleo's Dating Blog

First Dates

Posted on: August 4, 2010

Throughout my dating life I have had mixed feelings about first dates. Although dating was always assumed to be “fun”, a few years ago I realized that I actually hate first dates. The awkward silence, the nervous jitters, the disappointing conversation, the less then average first kiss- not things I want to block out a whole evening for. Drinking a bottle of wine with my gay roommate sounds like more fun!

However, after some careful reflection, I may have discovered the root of the problem to my first date qualms: me. Gasp! Could I be the reason why first dates are so uncomfortable? Let’s break it down.

I do not like forced conversation. Some people say they could not live without music. That music makes their soul feel different then anything else can. Some say they could not live without travel, without food, without exercise, without facebook. I could not live without stimulating conversation.

I am not satisfied with an evening, work day, text message, or date unless the conversation gets below the surface and sparks my intellect. I want my soul to feel alive and to learn something new. Obviously however, some topics are more stimulating then others. I prefer conversation directed toward why people think the way they do, act they way they do, and why they make the choices that they do. For example, I once dated a guy who went in depth about how microwaves work. Although interesting for 2.32 minutes, needless to say this relationship did not last.

I believe I like great conversation simply because of the way I was born. Understanding this helps me to understand that not everyone feels the same way. One of my most intelligent friends (we will call her Ninja) explained to me her reasoning. Although completely capable of holding an in-depth conversation, she often does not see the point. She argues: What is tangibly different with either participant’s life once the conversation is complete? What will really change? You talk, I talk, we both listen, but in the end we will go home and do exactly what we were going to do if the talk had never taken place. Is someone else’s approval or disapproval of your actions really that important?

Honestly, I do not know the answer to these questions. To me, the answer is not what’s important. When I am in the midst of a stimulating conversation, it is as if there is no one else around me and nothing else matters. The world is at a stand still. I am made drunk by my connection with another person and it is the most addicting feeling. I love it.

Therefore, as little Cleo goes on a first date, the dream of reaching this level of communication is highly unlikely. It is rare to find someone willing to be completely candid and open with another person- especially with someone that is barely a step above that of a stranger (as many of my first dates are). I can only handle the “how many siblings do you have?” and “how was your day?” questions for so long. I can not fake happiness well enough to completely hide my boredom. Since there are so many fish in the sea, I find that I tend to have a two/three date maximum with most men. If I find the conversation boring on the first date, I can blame it on the first-date jitters. The severity of the boredom on the second date determines how forgiving I am to forgo a third.

Ultimately, my search in finding a suitor that can share the same passion for conversation as me is what makes first dates so unappealing. As my coworker once described her dating life, “There are many suitors but few that are suitable.” Uninteresting conversation is almost not worth the free meal (almost, hehe).

However, my focus on finding delicious conversation actually makes me better at dating, in my opinion. Instead of being worried about how I look, what I say, what he is thinking, or how the date is going, I am so focused on being honest, open, witty, and genuine that the male will 99 times out of 100, want to see me again. It does wonders for the ego. There is nothing quite like a confident, beautiful woman with a mouth with something clever to say and two ears that listen.

My advice: find that thing that makes you feel alive. Whatever it is, don’t stop looking until you find it and don’t be afraid to be yourself. Love you as I love you.

All my love,



5 Responses to "First Dates"

I like Ninja’s as much as the next Kung Fu fanatic, but to suggest two people are not changed by a stimulating conversation may overlook the simplicity and power of suggestion. Any good conversation (and “good” may be defined as with meat or substance beyond the weather or “Entourage”) requires those involved to share thoughts or ask questions. To do either of those actions, one must define, at least to themselves, who they are, what they already know, and what they want to know. So, it follows that a reassessment of oneself lends the opportunity for redefining, for better or worse. I speak mostly from personal experience, of course, so I may be partially or wholly wrong. Until, a great conversation changes my views, I’ll continue to seek out interesting people with fresh ideas to teach me something.

Love this one Cleo.

I agree.

to both Cleo and Ninja’s credit, I don’t think the particular conversation from which that conclusion was reached can’t be summarized in one sentence. Ninja wasn’t aiming to imply that people are unaffected by ANY stimulating conversation, but rather, the fact that any stimulating conversation will become mind-numbingly uninteresting when it happens repeatedly. the discussion wasn’t about conversations that happen on first dates, or conversations about the meaning of life, or, more specific to this post, conversations that explore and analyze a person’s feelings toward a relationship.

there is undoubtedly, by definition, an intrinsic value in any “intellectual” conversation. nevertheless, when these conversations are about your feelings toward a specific person in a specific relationship, I think there is a line at which just discussing the problem or exploring your emotions begin to lose their importance.

in Cleo and Ninja’s case, the conversation was about feeling lonely. yes, acknowledging your loneliness is an important first step, thinking about it and discussing it a second, and accepting it a third. but those are only the first three steps – steps from which to move forward, not routines by which we should follow.

obviously Cleo is not suggesting that we fall into a continuous cycle of acknowledgment, discussion, and then acceptance: it is precisely this repetitiveness that Ninja meant to highlight. at some point, the value of these discussions will stop being derived from the conversation itself, and begin being dependent upon the actionable conclusions that can be drawn from them.

so yes, the first time, I talk, you talk, we listen, and we go home more aware of how we’ve felt. the second time, more aware of how we are feeling. the third time, how we want to feel. the fourth? we figure out what to do to get there.

that said, this has been an excellent first conversation. thanks Cleo :)

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