All good things may come to an end…

This is a little awkward given my last blog… but Jack and I are on a break. At least, that’s what I am calling it. I’m not entirely sure he’d agree with that statement (honestly he probably wouldn’t). Whether we call it a “break” or “breaking up” I have been very taken back by both the decision and most of all my reaction.

My last real heartbreak / non-divorce break up  was back in high school. It was my senior year boyfriend. We dated most of the year and my weekends and evenings revolved around seeing him or talking to him. We went to proms, graduations, and became best friends. This relationship ended (as many relationships during this time)  when he went off for his college journey across the United States. I still remember getting a call from him in a hotel half way and me crying the entire time while talking to him.

My adult experience with a heartbreaking break up is limited to the devastating ending of my marriage. Not really something I think will be mirrored in my dating relationships. However, when I think about breaking up in the dating sense two reactions come to mind.

One is the movie version of a break up. The woman eating a tub of ice cream in front of a sappy movie. After a night of this she goes out with her girlfriends for drinks and meets a new man. The other image I have is a little closer to home and what I typically see on Social Media.  This starts with #relationshipgoals photos, followed by a few passive aggressive quote posts, and finally a photo with a new guy. Neither of these break up situations seem to mirror what I’m feeling and how I’m reacting. So my purpose for this blog is to tell you my unfiltered and not social media approved truth

I’m completely crazy…

My co-workers and I were talking about this idea of a crazy meter for women that men use. I’m not sold on this idea but it’s definitely been an image that I’ve had in my head for the past couple of days. I would say I’m normally pretty low on the crazy chart (but I mean all women would say that right?! So take it for what it is). I get about an hour of crazy in every couple of weeks then talk myself out of it. However in the last few weeks, I’ve had the image of the Price is Right yodeler going up a metaphorically crazy mountain.


It started with the initial break up. In the first hour I was angry, crying, in shock and laughing. This was followed up but a period of processing. By processing I mean thinking of a 100 questions, asking Jack 200  questions, and using social media to my investigatory advantage. 

The craziest (we are not going to judge Jill) moment was when I created a VERY clearly fake dating profile to see if he was active in the dating site that we met on. This was a 2 in the morning great idea. I quickly deleted the account within minutes and tried to find another answer. Not my proudest moment… by far. 

While the conversations with Jack brought the only answers it drew just one large question that I’ll never know. Yes you’ve identified something to consider in the relationship but why aren’t you fighting for us? A question that still goes through my mind. 

I’m completely lost…

I have no idea how I’m supposed to be during this time with Jack. I keep hearing that I need to give him time and stop texting. As a matter of fact if I answer yes to the question of “did you text him today?”  I get a laugh, eye roll, or another strong declaration “Jill you seriously need to stop!”

Apparently you’re supposed to show a guy that you miss him by acting like he doesn’t exist. Right now there are 10 things a day I want to send him or say. I try to limit myself to the top one and on rare days two. I just don’t see the value in playing games.

What I am going to do is put myself out there and let him know I’m thinking about him with a funny meme or activity I think he will enjoy.  Trust me, as hard as ignoring him could be, its much tougher to get a “friendly” reply back.

I’m completely sad…

Probably the most surprising thing is how sad I am. I’m a pretty tough woman. I’ve been through a lot in my life and have a “pull up your boot straps” kind of mentality. 

However, in the past few weeks I’ve felt like there is a dark cloud following me. I cry randomly only when I’m by myself. I can’t sleep and wake up at 3am thinking and crying.

I thought that since I’ve gone through a divorce that I’d be able to handle this type of thing. My heart has already been so broken and repaired it should be stronger. But what I found is that’s not true at all. One of dearest friends told me “No Jill,  the divorce just expanded your capacity for sadness. So now when you’re half way full it feels like a lot more than before.”  

I’m at a crossroad…

Now I’m a few weeks in, I continually think what now? I have been so sure in every part of our relationship. During our initial dating, then our friendship, and then our relationship I’ve had a peaceful feeling about us. Something that says “Don’t worry Jill it will be okay.” What do I do with that now? I’m not sure. 

After all of this stuff and reactions I would be “in it to win it” with him tomorrow. The way I see it, we are both adults trying to figure out how or if we can combine our lives. This is something that should be taken seriously. If Jack needs time to think about things I’ll be waiting… Not forever but long enough. This may be precieved as desperation or lack of self worth but  I know deep down our dating adventure is worth waiting for. 

PS Jack does not read my blog unless I beg him twenty times to check it out. So again he will not read this one. 


How Out of Tune Am I?

So let me tell you a little secret about me… I sing in the shower and car ALL THE TIME! Like legit sometimes for an hour. I always wonder if my neighbors enjoy hearing the cat scratching coming from my bathroom to the soothing beats of Adele, Sara Evans, Dixie Chicks and of course my fave Reba McEntire.

I love to sing in these environments and when there is little expectation (random songs at work)… karaoke… not so much. For the most part, I get really nervous and shaky. So one night at Jack’s and I special date night spot, the place where we started dating, I decided to be brave and sing the Dixie Chicks song “Wide Open Spaces”. It’s my go to karaoke jam and I’ve been singing it in my living room since I was in high school. So, I take a few drinks, start out the performance with the words from the stage “Don’t expect much, I’m okay” with a shrug, and begin to sing. Afterwards, I get a hardy round of applause from the audience. It’s not a high energy song like the Humpty Dance or something that gets the big cheers. The karaoke lady says to me “Wow you’re really good… you should come up here more often!” I smile and say I will.

Jack gives me a high five and is very complimentary and I’m feeling on cloud nine.


I’m sure you are all thinking this is going to be some great story about how I showed up the next week and got a record deal after my up to par song. But, that would not be the story of my life.

Let me give you a little background and #BTS deets to Jack and I’s relationship before letting you in on my next round of karaoke.  As you are all aware, Jack and I  went from four great dates to the friend zone during our early courtship. What I wasn’t really clear on was the reason why we had this change of relationship early on. I never really wrote about it because 1. I was really hurt by this and 2. I was still trying to figure out the reason why. Now having known Jack for well over a year I am crystal clear.

Before we start officially dating, Jack was not looking for something serious. He dated women but not exclusively. So then on the fourth date with me,  I’m offering to send him a reoccurring meeting planner for 30 days for us to start exclusively dating.  “Jack seriously you can just reply off the meeting planner when you’re ready to date. We don’t even have to make it a thing.”  I didn’t really know him well enough to push dating but I did know him well enough to know that we should start dating… tomorrow.

So after our baseball date Jack goes radio silent… “ghost like” you could say.  I continue to message him here and there. Not crazy because I do have some common sense. Then after a few weeks  I get a message back and boom we’re best friends hanging out and messaging. Not officially dating but taking it slow as friends. I learned that was the way to keep him around because I really loved talking to him.

So back to the present, a few weeks ago, we go back to our special place. We order food and kept the drinks flowing.  Several  beers and bloody marys in and I’m feeling really confident in my performance.

I quickly sign up for my song choice and am the second name on the list. I even tell Jack “try to get a snapchat of this so I can share it on my story”

It was a new song for me “Born to Fly” by Sara Evans. The music begins, no self-deprecating words are spoken to the audience, and I’m bouncing to the beat.


I’ve been telling my dreams to the scarecrow…

And I’m off… not like race car begin off… like American Idol auditions off.  I can tell in the first line in the song. I’m panicking and I can hear my tune get worse and worse. I can’t catch the key and the ring tone karaoke background is not doing me any favors.  The once adoring  karaoke fan lady is now singing next to me trying to get me into tune. I quickly get through the song eventually going into a speaking the words mode. I felt maybe a more serious spoken word performance would work better than what was happening. As the final portion of the song is playing the karaoke lady whispers to me “Go ahead and choose another country song then we can sing it together”. Not the encouraging words of before.

The song ends and people stare. They don’t know whether to clap and the crowd is silent  except for a few pity claps. Then there is Jack. Jack the guy in my heart and now the guy seeing my karaoke demise. He is holding the phone up trying to do a video like I suggested. He’s such a sweet guy and wanted to be supportive until my cover performance end. I see him with the phone and very clearly into the microphone say “Come on Jack, you’re going to be my future husband one day you better clap.”

Lucky for me he laughed, clapped, and has spoken to me many times since. To a guy that was once afraid of a “small meeting planner” was now on board with being called out in public with another Jill crazy timeline declaration. I’m one lucky lady for sure 😉