The Twenty-Five Year Old "Something"

Do you ever feel like you are consciously setting yourself up for disappointment? I know this decision is probably going to hurt in the long run but right now it feels good enough that I just don't care. I think I do this a lot with boys and perhaps in relationships in general.


For instance, I caught you up on the initial meeting and flirtatious banter with my financial planner when I wrote a month ago. Well a lot has happened in the last 30+ days, but rather than write every moment that has made me swoon; let's get to the current issue at hand:
This boy is going to break my heart.

Things have progressed at a slow and easy pace. I still trying to decide if 'slow and easy' is just a positive way at looking at mildly interested. I hate when relationships feel lopsided or when you just don't know what's going on. 

The lack of definition here, has been plaguing me for several days. The more I chat up my crush with my girl friends or get asked at Cheers about JFK, every one seems to have the same question... What's going on with you two?

To which, I have no idea. 

So over my pre-date therapy session/beer with Sam Malone, we dive into the vagueness that is this new relationship. We have great chemistry; we get along really well. It's always fun and light-hearted. But I feel like I am in this anxious state of wondering what's going to happen next... I do not have "go with the flow" in me. 


This is not a comfortable place for me. As Sam Malone pointed out tonight. "You aren't use to this casually dating thing" No sir, I am not. I like clearly defined "relationships." If you like me and want to get to know me, then you do so but I require undivided attention and a lot of it. I am pretty up front about this expectation but not in this case. 

We are in some uncharted territory here. There's been no DTR (Defining The Relationship). There is no expectation of exclusivity. I am "something" (dating, seeing, talking to, sleeping with... something) a twenty-five year old. I've never something'd a twenty-five year old, not even when I was twenty-five. In fact when I was his age, I was a stay-at-home mom planning on marrying Mr. Toilet. I have no idea how to be in this... whatever this is.



It's exciting at best but for the most part nerve racking. I like this guy, I think he is one of the coolest people I have ever met. He's well spoken, educated, driven, well-rounded, and completely put together. Did I mention he looks damn good in a suit? This kid, and yes I call him kid, is the total package. He makes me nervous and giddy. I love spending time with him and I am excited to talk to him every chance I get. I'm kind of smitten but I can't shake the feeling that this kid's going to break my little heart... That's being a bit dramatic but at the very least he might possibly bruise my ego. 

So tonight, Sam tells me I have to some how talk about this. I need some sort of definition because I don't want to get my feelings hurt and end up hating him. Sam knows me well. But I am a total wuss. I don't really want to bring this up because I like how things are, I like the way it is progressing but to me I think it is progressing, I don't know what it is to him. I don't want to ruin it, I don't want it to stop; I want it to move forward but I definitely don't want to be an idiot about things. 

If this kid is like, "hey this girl is cool, she is a good connection as far as people and networking business wise and sleeping with her on occasion seems like a fun way to pass the time." I want to know that... I also want to know if there is some other girl that is cool, that sleeping with on occasion is fun. I don't want to conform to the constraints of a serious committed relationship. I just want to know what this is... I don't like calling it a "something."

Some of our past conversations have touched on long term plans and not being compatible in the future. Which is a little scary to me but as a twenty-five year old guy, the future still seems like this distant place. He's got all the time in the world to meet some one, fall in love get married and have kids... his 10 year plan does not align with mine. In ten years, I'm like 40. How do people do this? How do you not over analyze something that is so far so good? How do you control the neurotic desire to define a relationship? 

I need something so I know what this something is!

The best I could muster tonight was this little wimpy conversation... There was a couple at the restaurant, sitting on the same side of the booth. I jokingly said I wish we sat on the same side of the booth. He knew I was kidding and laughed, that's not going to happen. This opens the door for me to bring up how completely anti-PDA he is... He agrees he's not, yet defends himself with the whole not cuddly affectionate person speech, which I get. I am not super lovey-dovey either, unless I'm drunk. His comfort level and mine really aren't that far off but I am going to need him to graduate from awkward side hug to actual kiss when he sees me. He laughs, concurs and says, "You know what this is? Progress"


He doesn't want some crazy, intense, fast-paced relationship nor do I for that matter. He expresses that he likes what this is and brings up my joke about 3 week relationships. He asks me, some what seriously, when I am going to get mad and be done with him, which usually happens within a three week time frame. I explain that this is moving differently than anything I have had in the past and I am not really worried about it. We end the conversation, promising to be honest with each other and to be respectful enough that we can always maintain a working relationship and a friendship. 

This conversation gave me a little peace of mind, at least enough to not force him into some drawn out conversation about his feelings. He knows I like what we have and want it to continue but with a little more substance, a little more attachment. But I still want things to move at this nice leisurely pace. 

I am still not ready for something super serious. I am focused on my career more than ever and watching my daughter grow up before my eyes. I am not financially as stable as I would like to be but I am working towards some good goals that need to take priority over a boy.


I really like JFK even though this is all so different for me. I usually date these older guys and there aren't many questions as to if they dig me. There is however quite a bit of deceit, at least in my experience. So hopefully this is a good change. JFK does have the one thing I always look for in a guy: Someone who makes me want to be better. He challenges me and I respect him. I want to be this best version of myself, the version of me I love the most, the version I should strive to be all the time. Some times a little motivation can be found in crushing on your financial planner.