The Dating Experiment: Update

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About a month ago, I introduced you to the Experiment, “Most beautiful man on the planet” (he wrote that) — my unconventional relationship with a man that started off at the beginning of the year. The unconventional part: we’re dating but not dating but do couple things. Sure, why not.

It’s time to check in and see how things are going.

She Said

At the time of writing the first post, the Experiment and I had been hanging out for about a month and had established a pretty consistent schedule; going to a local bar for a couple of drinks mid-week (where I’m sure they think we are a couple), grabbing a movie, checking out a new place for dinner. My mother and friends then knew of him as “this dude who is a friend but not a friend…I can’t explain it.” Several social events introduced him to my friends where I would later get the “Why don’t you see where it goes,” eyebrow raise.

We were not dating and things were going great.

And then a pivotal moment happened at a party where a friend of a friend made an introduction to us with the, “How long have you been married?” line.

(Disclaimer: a lot of the people at this party were married so I can see the mistaken assumption.)

We both laughed it off and didn’t bring it up again, but it was shortly after that moment that a slow tailspin began that ended with us both saying simultaneously one morning, “We should slow down, shouldn’t we?” We couldn’t agree fast enough.

Whomp Whomp. The unwanted scenario, the part where things get complicated, had arrived.

Now, at this point, the Experiment was starting to become an emotional staple and a consistent warm body I could call on. Consciously, I knew where to put him — right at the edge of comfortable. Subconsciously, however, I was still wary. What if I was falling for this guy and then the rug was about to be pulled from underneath me? What if I would never fall for this guy and fall for someone else, hurting him in the process? Could this unique friendship simply be just that? What were we turning into?

And even if I imagined that he was ready to move forward and jump into a relationship, a part of me didn’t want to be with him just for the shear fact that I feel like he needs to experience Chicago as a single guy, having just returned from living abroad and being in a long-term relationship. I want him to spread his wings, get a taste, get more experience in a place that I was so familiar with. (Actually it sounded more like this, “You need to get out there and tap some ass.” Not sure what girl does that, but I did. He doesn’t like that.)

We decided to slow down and see each other less frequently, but now, I had a way out. I could walk away and never look back. Should I take it?

For about a few weeks in this new zone, things were weird as I stepped back to reevaluate what I wanted to do, creating even more rules, like asking him to not call me “Babe” as that could be too confusing; if I was a box girl, my box was getting smaller and smaller. I was one foot in and one foot from kicking him out. He was ready to take either.

(Another disclaimer: I went through a brief ‘losing my shit’ moment during this time that the Experiment was fully a part of, so my leaking crazy I’m sure had a lot to do with the need to slow down. He probably thought I was going to explode, but he did a great job of dealing with my ranting. Thanks darling.)

And then, maybe it was me actually losing my shit, maybe it was me seeing how crazy and analytical I had been, maybe I just wanted to gamble, but one day, I, the ultimate rule-maker and box-resider, asked the Experiment if we could drop the rules, all of them. Like stat.

I was exhausted.

I wanted to break free.

He was initially shocked by this given my absolutism, but given his carefree M.O., I think he was relieved I had finally jumped on board. We were finally on the same page. The ship could sail. So we plunged ahead, with no rules on the table outside of not talking about what happens with the opposite sex outside of our time together. (This is still the case and I have zero idea what he’s doing outside of our time. Although, the inevitable did happen since we are both on the same online dating platform and he sent me a message. It was the first time I blatantly told someone to leave me alone, sorry dude, you can’t cross the line like that.)

You may be thinking that with no rules on the table we stopped kidding ourselves and made it official…

No, we are still the same minus our idiosyncrasies creeping in, and nothing dramatic has happened. Our conditions are still there. He’s waiting for the fog to lift while he transitions into a new life; I’m trying to get my emotional shit together by opening myself up to vulnerability and happenstance or just trying to accept that maybe men and women can be intimate friends. It’s not easy and I jump back and forth almost daily. In the meantime, we are enjoying each others’ company and dialogue.

I’m working on fighting my instinct to run from something I can’t control, kicking and screaming along the way; he’s busy building me a bigger box.

He Said

I spend a lot of time thinking about who’s the naive one: me for my easygoing ‘if it feels right’ attitude, or her with her constant analytical-mindset. If I’m to complain, the dating? process with her can be quite difficult, because at times it’s like courting an administrator who is labeling and filing actions as they happen. I am, by contrast, laissez-faire.

Despite whatever definitions were debated in the first ‘Experiment’ article and this subsequent one, Her and I are still on a typical relationship development course. We’re past physical and intellectual attraction and are at the particular point where all the idiosyncrasies that make us human start to creep out. For example:

Some (but not all) things about me that annoy her:

  • I can be maddeningly absent minded.
  • I have a horrible time being direct in conversations.
  • I’m a cuddle-whore and have a tendency to kick her blankets to the back of the bed. He’s a cuddle killer. I largely sleep alone, diagonally, girl needs her space. (If the girl wants space enough to sleep diagonally sans cuddles, she shouldn’t be inviting me into her bed.) Touche.


Some (but not all) things about her that annoy me:

  • She talks A LOT (like, if I don’t interrupt her, she’ll just go and go and go and go). Because you’re not interrupting me! That’s supposed to be a good thing!
  • She can be controlling (example: recently we were in a conversation where I wanted to make a point by using an anecdote, this annoyed her because it meant I was going to meander instead of coming to the point directly, so she tried to make me come to the point directly which was like taking away the hammer and then asking me to hit the nail). This bit particularly bothers me because she, herself, is a chatterbox. But I get to the point 😉
  • Her bed is covered in one million tiny blankets. Uh, it’s been negative degrees for the past two months, darling. Uh, one word: Comforter.

I have a rather morbid relationship philosophy: You can’t know a person until you know their bad side, and you can’t love them until you’ve wanted to strangle them.

The point here is that we all have shitty sides. We’re messy, bossy, or bitchy. When we get angry we throw tantrums or break things or slam doors and never return. Everybody’s got a shitty side and we all do our best to hide from the people we’re interested in because we don’t want to send them packing. But, if you spend enough time with someone, you’ll start to see all the bad bits.


You know you’re there when doubt sits on your shoulder and you ask “Can I do this?” / “Is it worth it?” / “Do I like this person enough to deal with this shit?”

When I started dating/ not-dating this girl, I was upfront with all my major issues. Ever since then, I’ve been open about everything. We are just beginning to annoy each other, and I’m sure that the “Is s/he worth it?” test is coming up sometime in not-too-distant future. But, this doesn’t bother me; it’s part of the process.

As I told her one morning a few weeks ago: she’s being exactly who I need her to be right now. And, the minute that’s not the case, I’m going to tell her.

She Said


He’s right. I have been a piece of work these past few months.

I blame it on this hell of a winter, my raging hormones, being stretched too thin yada yada … (Not as bad as  Tyra but there were moments, oh there were moments.)

We’ve come to realize that, while we have similar interests, we are completely different people.

More importantly, however, is that I’m slowly digging myself into a situation where the need to seek a relationship has started to fade away, and I feel myself becoming comfortable with being single as I can potentially find all I need in my various relationships. For someone with mild commitment issues, and getting closer and closer to being set in their ways, this is the perfect place to be.

And that is a danger zone.

I agree that we are approaching the phase where it may be ‘make or break’, you can only suspend reality for so long, but until then we will continue exploring Chicago together, sharing recipes, bouncing off ideas off of each other.


And, if he makes it past Spring, he’ll delight in my one, sole blanket.






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