Free Dating: Your New Guide to Single Enlightenment

Apologies for the long dramatic pause between postings. That's what moving to a new city will do I suppose!

Well I've been off and running and have been dating and enjoying some of the men of the greater Chicagoland area. Baseline conclusion: most men are mostly the same most of the time. Got that? Good.

So, I've been discussing with guy and girl friends alike about the pitfalls of being single, the suckiness of dating and why we all do this nonsense in the first place and I came to a pretty fun conclusion that I think I'm going to stick to.

My conclusion is that once you realize how silly, stupid and awkward dating is, the more fun you can have with it. Don't take it seriously is the bottom line. Call it "Free Dating". (Similar to Free Running, which I mistakenly called Free Basing once... boy was that awkward.) In this Free Dating, you more or less take it as it comes.

For instance, first dates are horrible, we can all agree on this one. Nothing makes people more nervous than meeting someone who may or may not reject them without really knowing anything about them. Trust me, it used to strike daggers of fear into my being. I mean in reality you're instantly being judged, its like the American Idol of dating. (If only I had a condensed tape of the "audition" episodes of my dating life... how perfect would that be?). So why take it so seriously? I'm not saying be a total jackass about it, but I think we all need to stop worrying about the other person and what they're feeling and only go with your own intuition. I consider myself quite a dating chameleon in the fact that I can pretty much change up my style and personality to accommodate the person sitting across from me. Call it date-switching. It's a fun trick I've picked up over the years. But lately I realized that all its doing is returning men to me that I have utterly no interest in being around, because that's not really who I am. So, rule on first dates with Free Dating is: "Screw it. Do you."

Now one of the things that drives me absolutely crazy with dating coaches, advice givers, mothers and BFF's is that they tell you "avoid awkward conversations like religion, politics, money, etc." Why? Think about it. These are three of the main things that married folks argue about and possibly get divorces over. Maybe its because someone told them not to discuss... hmmm maybe? So rule number two with Free Dating: "Discuss whatever you want."

Finally the most IMPORTANT aspect of free dating is just to have fun with it. In the end you're out, about, meeting someone new. Sometimes the person has nothing in common with you, or you aren't very interested, well so what? Try to enjoy the time as best as you can. Be silly, laugh a lot and let yourself be fascinated by the fact that you are meeting someone outside of your circle. Rule number three "If you can't be with the one you love, love the one you're with." Well, maybe not love, love. But, just enjoy the moments. You did take the time out of your precious day, don't totally waste it.

Thank you... the offering basket will now be passed around.

Red Light, Yellow Light, Green Light... GO!

As I was driving through my 3 stoplight hometown I remembered reading about Stoplight parties in college. I will admit, I had never attended one of these events, but as I was driving I couldn't help but think, "Why can't real dating be like that?"

Now, if you are not familiar with stoplight parties, the basic premise is that you wear a bracelet around your wrist basically telling people at the party what you were looking for. Now I believe it was up to the discretion of the party thrower on what those designations were but the general gist was red=not looking, yellow=maybe after a few drinks you could convince me, and green=yes I'm ready to be laid tonight. I believe some intelligent junior highers developed a more sophisticated code with these parties and wore other coded type bracelets that indicated what sort of sexual acts they were willing to. Bravo public schools, bravo!

So yes, stoplight parties are all fun and wonderful, but what if dating was similar? I mean what if you could wear a certain color bracelet at the grocery store, bar, library, train, wherever you meet people and it indicated what you were looking for, whether it was a long term relationship, a fuck buddy, a one night stand, a sugar daddy, or nothing at all. My life would be so much simpler I swear.

I am a firm believer that men are usually pretty clear on what their intentions are with a woman, but us women being the overcomplicators that we are, inherently add complexity to their intentions to the point where it all becomes giant relationship mush in our heads and the next thing we know we have ourselves full convinced that the guy we slept with the night before after too many trips to the bar is definitely the man we should be marrying. Yeah, we're THAT f'd up.

So, if we all wore little bracelets that denoted what we wanted then there would be less confusion. I'm sure some of you naysayers in the background (yeah I see you), are saying "Whatever, everyone would just lie about what they want just to get what they want". Well, smart ass, I have my Master's more than one thing, sooooo... my brilliant plan is to make these bracelets like mood rings. GENIUS! Thank me later. This way, your mood will dictate what you're looking for that evening. So, next time you roll to the bar post-breakup and your bracelet lights up like a Christmas tree and says "Looking to hook up!" then just blame your hormones, not your bad choices. Problemo solved.

Anyways, I know this is an absolutely ludicrous idea, but it still begs the point that communicating is one of the biggest barriers at the beginning of getting to know someone. So often we feel that we need to tip toe around the big stuff such as the "Where is this going?" talk, or "what do you want from me?" which is ridiculous. I cannot even count the amount of times I've gotten to the point of being around someone thinking "I really like this person, and want to date them" and all of a sudden I bring up that conversation (of course after I'm emotionally attached) and I get totally burned when that person is like "Oh, I was just looking for friends." Thanks asshole. Could have shared that 4 weeks ago. So, don't be afraid to ask those questions that many people think will kill a good thing. It will save you more than your fair share of heartache. Being open, honest and upfront will only bring you back open, honest and upfront feelings in return. I mean why waste your time on another guy just looking for a hookup when you deserve much more?

WWGMD? (What Would George Michael Do?)

All right, so I have a confession. Word of warning, if you’d like to keep your image of me in your head that I am an amazing superwoman who is the epitome of awesomeness, then click that X up in the right hand corner right now. For those of you who are gluttons for punishment, or just get a kick out of me being opposite to my outstanding reputation, then proceed.

So, the other night I was laying in bed “thinking”. (Take from those quotes what you will…). Throughout my dating experience I’m always asked by friends, family, random strangers, etc. what type of man do you want. Whenever I hear this question I get a very weird reaction inside. Kind of like someone kicked me from behind and then proceeded to knee me in the side as I tried to get up. That’s kind of a violent reaction to a fairly simple question right? Well, after hashing out some reasonings, my only guess is that I get that queasy feeling in my belly upon hearing that question because my mind starts chanting “Oh you have NO idea what the hell you want.” And, as someone who has strung through too many dates and has been around way too many male friends and heard too many female friends complain about men, how do I NOT know the answer to that? After a few awkward moments of dawdling, stalling and uttering more umm’s and well’s, I give the very standard “Oh, he has to be smart, cute and funny.” How freakin’ original.

Throughout all of my eloquence, how did I come up with that garbage rolling off my tongue? And once again my head starts chanting “You have NO idea what you want.” So, like any good self-fulfilling prophecy, I started to believe it, and I started to own it. I even developed the very fancy way of sugar coating this into something deeper by saying, “Oh well, I hate saying a laundry list of qualities, I just go with my gut when I’m around someone”. BULLSHIT!

So as I laid “thinking” the other night I came to a realization of what I DO want. And…it obviously racked me a little bit. What I want? One word: Protector. A protector?! Are you kidding me? Of all of my preachings saying women, get your own, do your own thing, don’t let a man be the end all be all, and then this nonsense pops into my head? Oh take my feminist card now…if I ever had one that is.

But no, I’m sure it’s not that dramatic, but it still caught me by surprise. Literally the thought of coming home to a man who wraps me in his arms, looks me in the eyes and says “Baby, I will never, ever hurt you, and I will never let anyone else hurt you because I want to take care of you for the rest of my life” made me damn near burst into tears. YES! Why don’t men say that? Or better yet, why have men I met not say that? Do they exist? Please say yes.

Then I realized that is truly what makes someone vulnerable. All my life I have been taught to be self-sufficient. As an adult that unfortunately has translated into a bit of a character flaw in which I rarely if ever ask anyone for help. Being able to sit there and say to someone, “hey, I need you.” That’s vulnerability. Being vulnerable is not sharing your life story front to end, it’s not taking risks on something outrageous, nor is it crying pools of tears to someone. It is and always will be one person admitting to another that going it alone is tough, difficult and at times insurmountable. True vulnerability is trusting someone enough to lean on.

Call this my Ah Ha moment where I finally realized that maybe this was the missing piece. It was not me being picky, or not knowing what I wanted, or never meeting the correct man. All along it’s been me not willing to trust another person’s strength against my own. So in the philosophical words of George Michael, “Ya gotta have faith.”

Chivalry dead? Was it ever alive?

Ok, this has to be one of my biggest complaints about men, especially up on the East Coast. Sorry, I am allowed to make that claim since I have lived in the Midwest and the South and this really is only a trend up here in the Northeast...so get over it.

Anyways, back to my point. Where is chivalry? The courting a woman, taking her to a nice restaurant, a play, a park, the neighborhood cafe, hell anywhere other than your black leather couch in your bachelor pad. I cannot even count the amount of dates where the effort of putting together a first date was comparable to the effort my 7th grade boyfriend used when he would casually stroll by my locker before our first class.

Honestly, I make so many decisions in my daily life when it comes to work and my own daily habits that I am mentally exhausted by the time it comes to the question from a man "So what do you want to do?". Men...word of advice, don't EVER ask a woman that. Show initiative and plan something. Literally the minute a man asks me to make a decision about how he should spend his money on a date with me is the moment I've mentally checked off the idea that I now have complete and utter control. Contrary to most men's belief, that control is not something most women want. As long as we can control our OWN lives, that's usually enough for our daily schedules. So do yourself a favor and figure out what type of date I would be interested in.

Now, men, figuring out what type of date to go on...that's the trick. So don't lose me here. Stick with me. Golden information is about to ensue. Here's the trick to figuring out the "type" of date a woman wants...ready? Here it is...listen. I know you've heard that before, but it's true. Women have this uncanny knack of never directly stating exactly what it is they want. Part of it is uncertainty with what a woman wants, but the really smart women drop "hints" simply to see if you are PAYING ATTENTION. Men that pay attention, usually are asked for second, third, fourth, etc. dates. Really our code is not that hard to follow. For instance, here's an interaction, let's see if you can read between the lines and pay attention to what "type" of date I was asking for.

Kassandra: "Oh I absolutely love sports! I've never been to a game up here though since I grew up in Ohio."
Clueless Bachelor:"Yeah I'm a huge Knicks fan, I go to a lot of games. You know what, we should meet up for dinner before I go to this Saturday's game with my friend."

Seriously? Let's review. I said I love sports (which should be ANY man's fantasy). Secondly, I said I've never been to a game. Now wouldn't that be a perfect opportunity to say, wow I have an opportunity to make this a memorable first experience for this woman, something she'll always remember as her "first Knicks game". So, blunder number one, not picking up on the "hint" to take me to a game. Blunder number two, you just told me I wasn't worthy of your entire evening, but only useful as a pre-meet before your super awesome fun night with your friend. Way to make a woman feel amazing. And he wondered why I said no?

Either way, men have really gone off the track in terms of putting out the effort to make a first date a memorable experience for a woman. To this day, people in my parent's generation can remember their first dates to the tea, including what they wore, what movie they saw and how the entire evening went. I could barely tell you the first and last name of the guy I went on a date with the other week because it was so unmemorable.

Showing effort to women is almost a guarantee that they will respect you, regardless of your awkward first date traits such as sweating, stammering and forgetting to pull out her chair at dinner. And yes, we notice the ones who took some planning with their first date.

So fellas, keep the chivalry alive. Spend a little bit more money than the $20 you were planning on dropping at Chili's, or even get creative and do something FREE...Central Park or Battery Park is perfect to just walk around and get to know someone. You may thank me later.