From Hooptie to Hottie

Growing up my family had a car we lovingly called the “Junker Clunker”. It was a small yellowish (I think it used to be white) hatchback that had duct tape holding the key components together. When I was younger my dad would put Simpsons puffy stickers on the dash to keep us girls entertained in the front seat. However,  we still would hide in the seats and have our dad drop us off a few blocks away from school.

As I got older, I remember waking up at 5:30 in the morning helping my dad push this same car down our driveway hill to get the car started. Sometimes it took several times and I still remember my dad and I having to push the car back up the hill after a failed attempt.  I remember the joy when I’d hear the patter of the starter and engine.

My first actual “nice” car was my Toyota Corolla. My ex and I bought this car during our marriage. I loved the doors locked with a clicker and it had no duct tape! During the next couple of years, we bought a couple other really nice cars. However, the Corolla always remained.

So when the tough decision of separating out assets came, I wanted a piece of this memorabilia (also no car payment since I wanted the house and mortgage).  The nice new look of the car had slowly disappeared with time. Betsy weathered a hail storm and had the marks all over to show it. After my divorce my car then suffered even more set backs. A blown truck tire that did damage to my grill and then an “accidental” hit of a driving cone on the highway. While all of these damages were cosmetic old Betsy continued to drive and without any major issues.

So recently, I’m staring down the odometer and I realize a few things:

  1. I’m getting close to 200,000 miles
  2. I don’t like to ask for help so if I’m on the side of the road I’m going to panic
  3. I drive too much and too far everyday to be stuck on the side of the road
  4. I don’t want to get to a point where I feel like I need to buy a second car quickly without research

So with great hesitation I make the decision… I need to buy another car.

So I begin the process. I apply for a pre-approval and decide on a budget for the car payment. I look up car prices and begin to browse online for potential cars.  I am excited about the process!

Then it hits me… I’ll actually have to deal with a Salesperson if I buy a car. It is at this moment I panic. Like legit panic.


I was chatting with my good friend from work telling her about my desire for a new car. I can feel the anxiety coming up while I’m telling her where I am in the process. I am trying to stop tearing up and instantly become overwhelmed… even just talking about it. We’re having a great conversation and she finally says “Jill, why don’t you just ask Jack* to help you?”

I instantly say No. I could not imagine asking him to help me. I begin to rationalize in my mind all the reasons why I shouldn’t ask him. I mean after all he’s very busy, has many people that depend on him, and is in a busy part of his life. Isn’t my job to help him feel relaxed?! Not add something to his plate?! But after a few minutes and a very patient conversation (on her part! she’s awesome!) I realized that he could be a GREAT resource to help me navigate the dealership waters.

So, the next date Jack and I have planned was an all day date. It started with a trip to the local market, then a park, and then a local brewery.  We were having a wonderful time together, yet, all I can think about is this big looming question that I know I need to ask. So, after a few hours (and a few drinks at the brewery) I tell him “I really need to talk to you about something.”

His eyes get big… see picture of the baby above. I can’t even grasp what a dramatic opening that is because I am BEYOND nervous. I can feel myself shaking just asking. Then finally I say “Can you help me find a car?”

He laughs and says “Jill, I knew this was going to come. You didn’t know that you can just spend $20 to buy a new grill for your current car.”

I instantly feel better and we both laugh. I’m a smart woman in a lot of ways but cars and car shopping is not on that list. I have been very lucky to have great people in my life that tended to take care of these things for me. I wasn’t looking for Jack to take care of it for me but to spend the time to help me walk through it.

Car Experience #1 (the late night almost run in with the cops)

So the next week, Jack and I are driving to his house after dinner one night. It’s about 9:30 pm and Jack pulls into a car dealership. I tell him “Don’t stop here Jack! We are going to get busted by the police.”

He laughs and says “Jill, I highly doubt the police are concerned with the couple driving around in the family SUV looking at cars. Trust me. I got you boo” I’m telling you… that guy is hilarious! I’ll admit it…he had a good point.

So we proceed to drive around and stop and look at cars. After each car, he asks me what I think about the style. If I like the car then we look at the gas mileage and actually look inside the windows. He does a great job of asking me questions and not really inserting his opinion unless I ask him a question.

We drive around a few car dealerships in the area and head back to his house. It was a perfect toe dip into the car buying experience.

Car Experience #2 (the all day excursion)

A few weeks later, I ask Jack to go with me on a Saturday to actually see the cars in the daylight. I research the night before and find a couple cars I’m interested in. We drive in his car to avoid any “trade-in temptation” because I knew I wasn’t ready to buy. As we’re driving to the first lot, I can feel the anxiety creeping in. I am trying to carry on a conversation with Jack and my arms literally start to go numb.  To be honest, this was the first time that I’ve had a real anxiety moment in front of him. He is very sweet and holds my hand.

As we’re pulling in I look at him and say “Can you talk to the sales guy for me?” Of course he agrees… this is game time for him 🙂

We pull in and Jack takes the lead. He tells the sales guy “Hi, I’m (insert real name here), but you can call me Jack.” (He likes to mention that he has a pseudonym in my life) ♥

Together we drive several cars. It’s funny how much we agreed on the cars and his feedback was spot on! He even noticed a mechanical issue on one of them and the sales guy agreed that was the issue (I would love to tell you what it was but yeah no idea). After a couple cars, I finally found one that I loved!  The price was a little high, so I decided to sleep on it and search for others of that make and model for a better deal.

Car Experience #3 (the test drive)

I found another car a week later that was the same make and model and cheaper in my area. I set up a time to go do a test drive with my kid. I wanted her opinion about the make and model before making any decisions. I call Jack ahead of time and we practice what I need to say if I start negotiating. He was very patient explaining what could be considered basic adult activities to me. I figure we all have our strengths *shrug*

I am greeted by a friendly sales guy in the parking lot. He’s a young guy, seems genuine enough to be new, and commanding enough to know his stuff. He brings me into the dealership to sign papers for a test drive. It is at this point that I am begin to feel the anxiety come up again. It felt like some intense frat house… but with snakes.

Actual text I sent to Jack

The sales guy, my kid and I go for a test drive. We enjoy the car and agree to come back and test drive the car later that week. I wanted Jack there for moral and common sense support before I have to start negotiating.

Car Experience #4 (the let down but a date on the up & up)

This is a quick one… Jack drives the 40 minutes for the mid-week test drive and dinner. The sales guy calls me 10 minutes before our appointment and says the car I liked sold that morning. He recommended another car to me but I passed. I felt bad that Jack had driven so far, but, he was grateful because he was hungry. It meant we ate a lot sooner! (Again a man after my own ♥)

We have a great dinner together at a pizza place with delicious pizza and beer… seriously how could I even be disappointed about a car when I have a hottie with me?!? What car?

Car Experience #5 (the slow death)

So after the disappointment of the sold car I hit the online shops again. I found another car at the same dealership that I LOVED! I mean really loved! I quickly set up a meeting for that Saturday morning and stalked the car to make sure it didn’t sell. Jack was going to leave on a family vacation, but I couldn’t miss this car, so I decided to go alone… it was NOT a good decision.

I don’t want this blog to go in a negative direction so I’ll give you a few insights to my car buying experience:

Apparently, the sales guys at this dealership cannot do anything alone and so a “big man on campus” type sales manager needed to be involved. So the friendly sales guy that I talked to before turned into a tag team duo. Good Cop & Bad Cop.

I told both of these men that I was torn between two cars. Their car and another at another dealership.  The other car was $1000 less but it didn’t have the heated seats I really wanted. (I’m telling you cheek warmers are essential) The sales guy also pointed out to me the difference in the mileage. This difference was about 10,000. To put that into perspective that is about 6 months of my driving (I have a long work commute).  I told them that the miles difference was not a big deal, repeatedly. I told him approximately 10x he listened to me approximately 0x.

Quotes from the sales guy(s) during my car buying experience:

  • “Oh come on Jill, I’m just kidding”
  • “Jill, here are the benefits of Pre-Certified ownership. (pulls out a pamphlet) I can take these away if you need the car cheaper.”
  • “My job is not to put together information for you to take away and research. My job is to sell cars.”
  • “You’re the one deciding to haggle here. You can imagine we are a CarMax. Just imagine there is no haggling here either.
  • “Well Jill since miles don’t matter to you, I have another car with 80,000 miles on it for cheaper. Would you like to take a look at that one?”

Now a cliff notes version about my time there that I think are very important to note:

  • I asked for a total discount on the car of $500 (meeting in the middle and was worth the heated seats)
  • The sales guy never told the sales manager the amount I was asking off. So the sales manager proceeded to hard push me. He made a couple of the comments listed above while talking about my cheapness which resulted in a 10 minute rant from me. This rant may or may not have included me welling up trying not to cry.
  • The sales guy felt bad and got me water mid rant
  • When the sales manager realized that I only wanted $500 off he apologized (I’m sorry I upset you Jill) *eye roll*, threw the sales guy under the bus, took $650 off, and brought me over balloons from a birthday several days earlier.
  • I was pre-approved for well over the car amount with a large financing company that they use “a lot”
  •  I test drove 1 car
  • I test drove that 1 car about 20 minutes
  • I was there for OVER 5 hours
  • I’m still waiting on a call back from their Customer Service Manager
  • I will never walk into that place again


Now, I know what you are thinking… I should have left. I know I really should have now. At the time I kept thinking that this was maybe the way that car buying went. I have heard about those creepy car dealership guys with their high pressured sales. Plus, did I mention my anxiety?! Sometimes it can make me not be able to think clearheaded and make good decisions.

Car Experience Learns 

  • I need to be vulnerable and just ask for help. It was really tough for me to ask but really made me appreciate Jack and our relationship more.
  • I will go to a no haggle place in the future.
  • I am beyond grateful for Jack! The entire experience made me feel like I can really count on him. Plus I told him that if this works out… he can do this from now on!
  • I love my new car! It was a celebration about an hour after it was over. I needed to take an hour to unwind then had the WOO HOO! moment!










The Business of Dating Requires What?


Do NOT read this blog if you are someone that believes in too much information… I’m telling you ahead of time it is going to cross some lines.

A little history, I have never really thought much about birth control. I have tried out various forms in my lifetime for various reasons but if I had a baby during this time I would have been excited.

However, now that I’m not married, having a baby brings on a whole new responsibility that is a lot tougher and more complex. I have made it my goal that if were to have another baby,  I want it to be under the “right for me” circumstances. Being married with a joint decision between both people. If neither of those things happen then a baby will not be in my future.

So a few months after I was divorced, I saw my doctor and we discussed birth control options. I knew the pill wasn’t for me because I knew my level of memory and could potentially be holding a baby within 10 months if I tried it. The shot wasn’t an option because if/when my circumstances align I would want a baby shortly after the decision. The patch would make me want to pick at it all the time because I do that with bandaids and scabs. Finally, an IUD seemed too permanent. So I went with the NuvaRing.  While a little weird to put in, I thought it seemed like my best option.

So I had that for almost a year and realized, while I’m not responsible enough for a daily, I was not even responsible enough for every 3 weeks. I spent more time trying to remember milestones to figure out what date I had put it in then if I actually just put it on my calendar. Yes! I know what you’re thinking… maybe this lady needs to rethink having a baby she probably won’t even remember to feed it…

So I went back to my friendly doctor and we brought back the IUD option. We discussed it’s benefits and the fact that it can be taken out by doctor at any time and you can soon get pregnant. I knew all of the factors aligning wouldn’t be for a few years (even if it is Jack*- oh he’s amazing ♥). I had time. So after a few steps (and a negative pregnancy test— whew) I made the appointment.


I’ll own this part… After reading about the IUD briefly I didn’t do a lot of research.

I took half a day off of work and made the appointment in the morning. I figured I’d had a birth control shot and felt fine immediately after, had a NuvaRing and felt fine immediately after, and a regular woman doctor visit before and felt fine… again immediately after… so how could this be any different?!?

Boy was I wrong…

I woke up bright and early to the birds chirping, sunshine coming through the window, and Rae Sremmurd “Swang” playing on my phone. It was a wonderful morning. I put on comfy pants, a warm hoodie and super fuzzy socks. It was Friday so casual dress day at work (yay!) and I was taking full advantage. I was really in heaven… comfy heaven.

I arrived 10 minutes early to my appointment and with a smile on my face greeted the receptionist and gave her my information.

She said “the doctor is running about 20 minutes behind but we’ll get you back as soon as possible”.

“No problem” I said as I sat down on the chair… blissfully unaware of what was about to happen.

I get called back to the room and they check my weight. It was about 6 lbs down from the first visit so I was feeling good! Just another bonus to my already relaxed day. I had to pee in a cup, and while never a favorite thing to do, it was relatively unmessy. Again… another plus.

I get to the room and it should’ve been my first sign. The room was on the other side from where I normally go. “Oh we’re going to the left here?” That’s weird I thought. The nurse tells me to remove my clothing but I can keep my socks on. I was glad because in my morning routine I put good smelling lotion on my feet and they felt so cozy in the fuzzy socks.

So I undress and wrap the sheet they have around me. The table is a lot different than I expected. It was very short and I didn’t know how to move the top part to offer back support. So sitting there unsupported, naked, hunched over, and a little cold… I waited and waited some more. I wasn’t going to take the chair that is always in the office because I had my business out and that’s just gross.

I continued to wait for another 45 minutes. Apparently, my definition of a “little behind” and the receptionist was a lot different. However, I remained positive. I figured this doctor is dealing with something rather important to keep me waiting so long. I mean after all what if a baby was being “surprised born” from the other room. Who knows?!?

So after 45 minutes the nurse comes back in and says “You didn’t have to take off your top half. We’re not doing anything with that.” Serious face. “The doctor just got back in the office and you’re second.”

So of course I run to get my bra and hoodie back on. Normally taking my bra off is one of the best parts of my day (you ladies know what I’m talking about) but this time with the no support I wanted to put that baby on.

So the doctor finally comes in about 45 minutes later… Yes I waited an hour and a half. He pulls out the other half of the table and immediately I think “Are you kidding me? I could have been laying down this entire time?” He then puts me in position and sweetly with that soothing doctor voice says this:

“At first you’ll feel a little poke, then a little bit of cramping, and finally a little bit more cramping for about 20 minutes. Then you’ll be done”

I shouldn’t have listened…

So the doctor slowly puts the instrument in “the business” and says “here’s the poke”. It’s really not bad! I mean it’s a little bit of a poke and then it’s over. I barely felt it.

I see the nurse holding the IUD and it looks exactly like the photos. A little bigger than I thought… but it’s not like they have it next to a dollar bill to get an idea of size in the pamphlets. So I’m not surprised.

Then comes the “little bit of cramping”… Let me just explain it like this… It feels like a long metal piece is going into “the business” and then trying to be ripped out “the exit”. Yes, I literally said “What?!?” and moved violently away from the doctor with the metal instrument in me. Little bit of cramping my ass… no literally.

He said “you can’t move” and while I agree.. I also don’t remember anything being that far up in “the business” that it may see sunshine on the other side.

Then he says the words a woman always wants to hear while your body is heaving…

“Tonya, please get me a cervical extender”


They then get a thicker piece of metal and once again repeat the process. This time I know it’s going to hurt so I remember my Lamaze training and breathe. Breathe.. breathe.. breathe..

It’s not helping much, but it’s not making me want to kick the nice doctor in the face.

Then it’s done. He puts away his instruments and tells me to lay down for about 10 minutes to help my body not pass out when I leave from low blood pressure. I’m laying down trying not to cry and also hoping I don’t pass out. The nurse hands me medicine (without water) and I lay there for the 10 minutes. Literally my stomach is having the worse cramps I have ever had in my life outside of childbirth.  Which I find ironic because that’s what I’m trying to prevent. I figure deep thoughts are what I need at this time to get my mind off of the baby elephant using my insides as a trampoline.

The doctor comes back in and gives me some final advice the pretty much summed into take medicine as needed and come back to see him. Apparently an ultra sound is necessary after this to make sure they “got it in the right place” because after all they are “going in blind”. Really comforting words to half hear through the pain. Then he leaves and opens the door once again “Avoid intercourse tonight and probably tomorrow as well.” I laugh… out loud… and say “yeah not a problem.”

So I granny walk to the receptionist. This time not as cheery.  I hover over her desk, making faces, talking like a zombie while she takes 10 minutes to find a time for my follow up appointment. I feel bad for her because you can tell she’s struggling but I can barely breathe so my empathy is about a 3. She asks me if I mind waiting while she talks  to the doctor about scheduling. I tell her in my best zombie voice that I’m completely open and to just leave me a voicemail with the time. I couldn’t imagine standing there one more minute.

I hobble to my car and really wish I had asked someone for a ride. The idea of driving in that much pain was not a good idea. I fumbled through my purse for the packets of Ibuprofen the nurse had given me because I had water in the car.  Now what I should have done at this point was drive home and lay down under my heating blanket. But instead I listened to the doctor and thought the cramping would soon stop and headed to work. I mean it was only 4 hours.

Now let me be VERY clear, everyone would have completely understood if I took the rest of the day off. I have a great job and very rarely call off so it would have been PERFECTLY fine. But instead, I made the wonderful decision to go to work and tough it out. I even stopped to pick up Chipotle because I had promised a coworker a working lunch meeting. Again, he would have completely understood if I cancelled.. but I pressed on.

I stood in line at Chipotle during their lunch rush and leaned up against the wall and prayed that I didn’t pass out from the pain. The baby elephants and turned 3 months and had gained a few pounds. I then went to work.

I knew my face was white and I won’t say I was at my best… but I was able to press on for the couple of hours. I heard a lot of “You don’t look good”.. “are you in pain?” and “go home” but I wanted to get work done and I was in back to back meetings and didn’t want to miss any important information.

I left work on time and then continued to cramp for the remainder of the night. It wasn’t nearly as bad as when I got off my feet and laid down. My pain cramping finally stopped a couple days later, just in time for my monthly to start.

Now that I’m out of this day I can truthfully say…


Things I should have done:

  • Looked up the process and side effects
  • Pulled out the other part of the table so I can lay down when waiting
  • Taken the full day off
  • Asked for a ride from a friend or family member… or hell Uber

Let me just say… if during my ultrasound they find the IUD isn’t placed in correctly… I’m going to go for the patch… picking and all.







“Who’d a thought (uh) that we could be lovers?”

So Jack* and I have been dating for 3 whole months. I’ve got to say that the one word I have for our relationship so far is Grateful. Grateful for our time, grateful for his effort, and overall grateful that we’ve come to this point.

So before I start this blog I have to issue a disclaimer… a LOUD disclaimer…

♥I am in the Love Eyes, he’s wonderful, everything’s fantastic, portion of the relationship! I reserve the right to go back on everything I’m about to write  (although I don’t think I will) ♥

So the thing that I figured out when we were in our 6 month “friend stage”  was how different we both are. He even called it out as a potential issue before we started dating. One thing that we both share in common is our ability to think about potential issues. I mean after all you’ve all read my blog up until this point, right?

We put the Paula Abdul hit single “Opposites Attract” to a whole new level:


Workout Routine

Him: Jack works out all the time. He runs and lifts and often talks to me while doing this. I actually enjoy it because I can go on long “stories” and I get a few word questions from him (always relevant) then another Jill monologue. Let me just say, working out has produced very good results!  Dayum! whew…

Me:   No… No… that’s not me at all. I did sign up for a gym membership and since the first of the year I’ve worked out twice a week (woo hoo go me!) I know what you’re thinking?! Oh Jack must have said something… But that couldn’t be farther from the truth. My goal for working out is to NOT feel like I’m dying when I go up a flight of stairs, plus Jack likes to do active things and I want to make sure both of us get to do the things we love.


House Maintenance

Him: Jack’s house looks like a freaking Pinterest board. It has nice throw pillows, pictures, and hand built furniture. He does house projects all the time. He has one small project in his basement that he made sure to call out when we were watching a movie. I laughed…

Me:  When I first got divorced, I took over the  house that my ex and I were renting out.  The house was destroyed by the renters. So my sister and my brother in law took over and made my house look very warm and welcoming. We worked for weeks on the house to get it exactly how I wanted. I love my home! However, my house is old and has a TON of projects for me to do. My current project  is to add DOOR KNOBS on all my doors…. yes you heard me right… DOOR KNOBS! Long story about the door knobs but long story short… the lack of hardware was completely my fault and over a year ago.


Him: His life is very structured and busy. I can guess most of the time exactly what he is doing on any given day. In order for him to get all the things he does his plans all the time. He knows exactly what and when he needs to do to get the results he wants.

Me:  I fly by the seat of my pants in most areas of my life. I am pretty laid back and make it my goal to get certain things done. I can go with the flow most of the time and while I don’t mind structure I typically go with my gut. It can be a little chaotic, but I get the basics done and with a little fun!

Chatting about Us

Him: Only like 3 people in his life know we are dating. He doesn’t tell anyone. Like anyone. He said this is typical for him for most things in his personal life. He rarely posts on Social Media and when he does he doesn’t even use captions to explain the significance of the picture. He even showed me how easy it is to just share a photo. “Like literally I can just click share and it’s done”

Me:  I write a blog… talk about him… share pictures of him on social media… post at least a selfie a day. You know the usual behavior of a young 20 something (trapped in a mid-30’s body).  Readers, friends, family know about him and basics his life. I’ve asked him if that bothers him and while I don’t think it’s his favorite he says he doesn’t mind.

The good news is that we are both agree on the important things:


Inappropriate is hilarious! The more offensive  the funnier it is. If you would be a little embarrassed to post it on your Facebook wall I’ll probably laugh. If you’d be a lot embarrassed I’d cry… of laughter.

We both enjoy a good meme and typically send to one another our favorites…

Not the funniest one… but I got a rep to protect

Always up for an Adventure! Both of us will get into a car and just go. Due to our schedules we haven’t had a chance to do this adventure together for longer than an hour away. I can’t wait for that moment! He doesn’t mind listening to my car karaoke and I don’t mind singing at the top of my lungs to everything 🙂

Communication is key! I haven’t met a guy so willing to talk about our relationship and what I’m thinking and feeling. He  is also very candid and honest with his thoughts.  He is pretty black and white which helps with my overthinking. I used to read into everything he said and to try to figure him out. I learned that he says what he thinks there is nothing to figure out.  If he says I like ice cream he means I like ice cream… NOT I wish you’d take me to the ice cream store… I can’t believe you didn’t think of that when it was hot outside.

Work is very important! We both are driven at work and get things done. We can work long hours and understand that it is important to our careers. As single parents your income is reliant on only you and we both love what we do. It’s nice to see a man so driven in life.

Family is everything! Our kids are important to us and the number one priority. We are both involved parents and look out for the well being of our kids. We haven’t even met each others kid(s) because we both believe in waiting until the right time to make those introductions. It’s not a rush and we both need to figure out us  and figuring out if this will last for a while before we add that dynamic to the relationship.

Yes, I do look at these differences and wonder where our future could be. I think the good thing about the two of us is we’re both willing to give a little. Sometimes life needs to be structured and sometimes a Netflix marathon is EXACTLY what the day calls for! It’s funny how I’ll say “Man I had a Jack day today and kicked butt!” and he’ll send me a picture of him watching a movie. Awww.. the photos of that or laundry on the chair just warm my heart and give me hope!



Now to learn to swim…

So I have an update for my last blog. Bear with me ladies and gents this will definitely be worth the read 😉

So Jack*, yes the guy from way back in my blog Do you Know Jack? , and I finally had THE conversation.

Let me first clarify something because I was asked about this.  Jack has never read my blog… Well once when we first started talking for about half a blog… then he stopped. But that was it. He has always said he would rather have the conversation than read about it. So, writing my blog before was really for advice and boy did you guys deliver!

So back to the conversation. We all know that I was drowning with what to do being lost in the friend zone. So I prepared a speech… a well thought out speech… a speech I ran by my closest friends… counselor… grocery store clerks… clergy men of other denominations.. you know everyone.  I wanted to make sure I was sending the right message, was vulnerable and saying exactly what I meant. I didn’t want to blow it because I’ve liked this guy forever.

So one Wednesday we’re texting ( like we do everyday) and he says he’s having a rough day. He was going to work out and then stop by and get a drink. So I gathered up enough courage and said “Well if you’re looking for a drinking buddy my hair and make up is looking hot!” I NEVER do that kind of assertive thing but I’m working on putting myself out there so I texted it. I then turned the phone over and walked away. I didn’t want to watch my phone for the answer … I needed the breather after the whistle notification.

So he replies… I breathe…and read “How about 8?” WOO HOO!!!

My actual look that night..

So now we have an unexpected hang out and I was pumped! I told myself I wasn’t going to have “the conversation” since he was having a rough night but would enjoy the night out with the hottest guy in my eyes!

We get to the bar and find out it’s Karaoke Night!! What! What! My favorite! We have a random guy come sit with us who explains how seriously he takes karaoke and Jack asks him all about his practice habits. I’m impressed because it shows me how Jack can go along with pretty much any conversation. His improv skills are off the chart. So Jack and I make the best of the night! We drink (a lot) and sing along with all the best karaoke songs! Can you say Miley Cyrus “Party in the USA”? Yes we sang along!

As the drinks are flowing we start being friendlier and friendlier. Not inappropriate for public friendly…just flirty. It’s cute and of course I like him so I’m into it. So after several drinks we decide to head out.

We’re walking to the car arm in arm and this is the moment..

I decide NOW… IS THE TIME… for THE conversation…

(Paraphrased conversation hitting the key points and I’m sure removing out a lot of hand waving, repeating myself and I believe dropped keys… twice)

What I WANTED to say: So Jack, I have really wanted to talk with you about something.

What I ACTUALLY said: So you want to hear the speech I’ve been practicing for weeks or do you want me to wait until the next time we chat? No seriously.. I’ve been practicing for weeks…for weeks.

HIM: Weeks? You’ve been practicing for weeks.. Yeah lets hear this..

What I WANTED to say: You know how I feel about you. I think you are one of the funniest people I know and I have a blast when we hang out. I love how good of a dad you are and how you remember all the little quirks about me. You make my day better when I talk with you and I know that I’ll be a better person having known you. 

What I ACTUALLY said: You know you’re great… like great… and wonderful (with giant hand motions)… like awesome. Did I say great? Funny!

HIM: Thanks Jill! You’re great too. 


What I WANTED to say: I have had a lot of fun with this dynamic we have but I wanted to let you know my experience during our time. 

What I ACTUALLY said: Yeah so let me tell you about me and the time we’ve been talking. 

HIM: Jill! You better not be ending this… 

There was no “what I wanted to say” for him to interrupt me. I should’ve thought of ground rules but golly geez no one interrupts Oprah when she’s giving a speech… so wasn’t on my radar. A total wing!

ME: No no… it’s not your time to talk. This is my speech pay attention. I’m not at the end and I’m not ending it. I’ll let you know when it’s your time to talk. 


What I WANTED to say: So during our time I haven’t really been able to give other guys a chance.  I have gone on several dates and even a couple dates with a couple of the guys and each one of them is in the friends zone before they even walk into the door. I even had a guy ask me to be his girlfriend and I turned him down. I have found that no one can compare to the connection we have. (Pretty much what was in my blog)

What I ACTUALLY said: So you know I go on dates right. Well two guys on Monday (yes true story) and I just don’t like any of them.  I go on dates and nice guys. Like really nice guys but no chance for them. None of them. They just don’t compare. No one compares.

HIM: Whoa.. that’s a lot of pressure.

What I ACTUALLY said (which mirrors what I wanted to say): No it’s really not. I didn’t tell you this because I wanted something from you. I am telling you this because I need you to understand my experience in this whole thing. That I’m not a cool girl. I’m not the girl that can really like one guy and then date other guys. I’m just not like that. I’m trying to be like that so we can stay friends but I’m just not. I’m just not cool.

HIM: That’s one of the things I like about you, that you’re not the cool girl.

Now I’m off the rails…. legit making it up as I go. That’s where I thought the conversation would end. Luckily for me it didn’t

ME: Then you go and get into an open relationship! What the f*&$k was that about? I mean really?!

HIM: Yeah I’m not… that ended a couple weeks ago.

Because like you Jill…

I’ve found out that no one can compare to you.

I always think ‘Can I talk to her like I talk to Jill?’ and the answer is always no. So you know what… we should do this. Like really do it. Let’s figure this out Jill.


My heart was racing at this point… but I played it cool and stopped talking. I mean after all what was I going to say?!

Then he read my mind:

 HIM: Why did it take me so long? 

ME: I don’t know. I’ve known it since day one. You’re just a little slow I guess. 

So it’s official. I’m officially dating someone that I am just over the moon about. I never thought that being friends first would actually pan out. The first time Jack and I talked I was timelines and demands. The second time (about 3 weeks later) I let it play out. I didn’t push anything. Tried not to message first. Let him take the lead. I didn’t go into it with any expectations. I had to fight myself constantly to define and figure out. I asked poignant questions when needed for clarification but didn’t push anything.

So here I am… I don’t know what the future will bring but my good friend Jackie sent me this when I started dating and I have applied it to this entire adventure:


Don’t worry though… I still have a lot of great untold stories from before I met Jack, while Jack and I were friends, and all the mishaps I’m making now that I’m actually dating someone. I mean isn’t asking a guy daily if you’re still dating totally normal?!

Can you drown in the deep end of the Friend Zone?

So over a year and half in and still single… like single… like totally single… in status. Why just in status? Well it depends on which part of me you ask. Ask my brain? I’m SINGLE… you ask my heart? It gets complicated. Yet another battle of mind vs heart.

That is because my friend I have been entered…pushed into the FRIEND ZONE and I can’t seem to get out.  Now there is this idea that I have heard that the FZ is just a myth. One perpetuated by the media and by sad people trying to figure out why they can’t get a boyfriend/girlfriend. There is also the idea that the best relationships start out by being friends. That sounds great… on paper.

On many guys’ dating profile they write “I want to be friends first then see where it goes.” When I read that…  I make a hard swipe left. (That’s the reject direction for all of my married readers). I  know it sounds really romantic and always works in 1990’s rom coms…

However, I am a 34 year old mom (yes I hear that clock ticking too), homeowner, dog owner, career minded woman that barely has enough time to prioritize the things I need to. I have friends for life, that I don’t make enough time for (you all know I love you! we’ll get together soon I promise). So the idea that I am going to make it a priority to add another friend in the mix is not an option in my head.. or at least I thought not.

Now I’m going to find myself in a bit of hypocritical moment.. and yes I’m calling myself out on it. I’m more than happy to have a guy friend that I’ve dated IF I’M THE ONE NOT INTERESTED. Then we can be BFFs all the way. If my heart is not involved I can be the best of buddies with people. I have many of these guys in my life. After all Some of these guys I actively dated and some were guys I went on a date or two with and we realized we’re friends.

These are the guys I ask life questions to:

What do you do when you run out of gas? Do you call the police? – This one wasn’t good.  It started off with a friendly lecture on how to read my gas meter… ended with call a friend, preferably him.

What printer should I buy? – I DO NOT want to look through reviews.

Why the hell doesn’t this guy like me? I’m amazing!- This one I like because if you’re my friend you probably think I’m amazing as well.. j/k I normally get actual practical advice on from this one.

Yet I find myself with a guy who started out with a different goal from both of us and now sees me as a “great friend” and is dating (not exclusively) someone else and it sucks! I find my normal black and white mind turning into a field of gray. Like drowning in gray paint.

I would imagine most people would just LOVE to have a guy that messages first everyday, randomly calls, remembers your coffee order, gives great advice, and is willing to go anywhere… I would too and I do..but I would enjoy it a lot more if it followed my black and white philosophy.

Instead I find myself questioning everything I do,  contemplating ending conversations, becoming disinterested in the dating game, and not even giving other guys real chances. What I can’t figure out is… how do you open your heart to other people when you have someone in there that doesn’t want in there?

Now the good news (because I always look for the bright side) and what I’ll probably learn from this situation is patience. I no longer get stressed out by no texts, timelines, and with labeling the relationship. I just really want to know that someone is open to the same goal as I am. Then we can take it from there.

So what is your philosophy on the friend zone? How long do you wait? or at what point do you realize that…






Can I Drink Enough to Make this Fun?

I (like many others) am constantly thinking about how I can improve myself and push past my limits. This is especially true in the dating world where I am constantly being confronted with uncomfortable moments. As I mentioned before, I am very awkward when meeting a guy for the first time. So when I learned about events from one of the dating sites I subscribe to I decided this may be a chance for me to get out there! For my avid readers, I have done a dating event before… but used a crutch and went with a guy. This time I was going to go by myself.

I found the perfect dating event. It was a brewery tour with a beer tasting about an hour away. I thought it would be a wonderful chance for me to learn to make small talk and not go to the “friend zone” immediately. I signed up and posted it on Facebook so mentally I was less likely to back out!

The day of the event came. It was a Sunday which was perfect because I had plenty of time to get ready… or so I thought. A little “Jill insight”- Once Fall hits, my life is all about watching football and especially the Browns. The event was on same day as the first game of the season… equivalent to your first day of school as a child (for those people not sports fans).  I went to a local sports bar and watched the beginning of the game. I had planned on leaving at the half which would give me an hour… instead I left with about 30 minutes to get ready. The game was really good and I couldn’t get myself to leave in time 😉

Go Browns!

So it was time to get ready for my actual dating adventure. I knew what I was going to wear and based on time decided to straighten my hair. I have found out after dating so much how to get ready in  record time so it worked out well. I was going to actually put myself out there and try to look as cute as possible (for me)! I figured it would help me stay confident… or at least look like it.

So I get ready… take a few selfies.. and drive! I listen to my music loudly and sing along to all my favorite jams.. (actual song that played that I busted out)

It’s driving me out of my mind
That’s why it’s hard for me to find
Can’t get it outta my head
Miss her, kiss her, love her, wrong move you’re dead
That girl is poison
Never trust a big butt and smile
That girl is poison poison 
So when I got there I am a lot more relaxed and pumped! I mean how can you not be?! So I showed up sat in my car a little bit nervous but ready…
I arrive about 5 minutes early to the event and get out of the car. The brewery is in small suburb of a larger city in Ohio and is in a nice brick building. From the door I see about 5 small tables to the right, 3 stairs to the left (leading to upstairs) and then the bar. Overall, it’s a small venue which makes sense for a local brewery. Inside there are maybe 6 people. No one greets me and I see a nice pretty lady sitting there with a beer. She has I’m “here for the event” look as well. I sit down because I am a little early. About 5 minutes later, a couple of guys walk in. The bartender says “Hey guys! If you’re here for the event you get a free beer.” The guys say yes and the bartender gives them a free beer. I mean if that’s the only verification, I will attend each weekend and say “yeah here for the event!” FREE BEER PEOPLE!

So about 5 minutes later, I notice that the number of guys FAR outweigh the women. There are literally 4 women there and about 15 guys. I’m sure each of you are thinking… “Whoa! Good odds!” Instead I’m thinking “Holy Smokes! I am going to have to talk to more people!” The room is really awkward with 0 people talking and I can tell 0 people are interested in me.

About 10 minutes later, the bartender says “Yeah if you guys are here for the event there are name tags and questions upstairs”

“Oh! The party is upstairs! Duh Jill!”I thought.  So I grab my beer and head up the three stairs… So yeah… a picnic table with a sign in sheet and name tags. One other guy. No talking. The highlight of the upstairs was the Nintendo 64.


A group of us begin to ask the questions to get the “event” started. We have a circle going and while the ages of the people vary greatly we are having fun. It was clear that this was not going to be where I meet my soulmate but I will ensure that I enjoy myself.

I decide to invite some of the quieter guys upstairs to join in the conversation. I am no longer nervous because the lack of organization is outstanding and that kills me as someone who leads quite a few meetings.  Downstairs there are all  guys and a female bartender who is certainly enjoying the attention of a few of the guys. The problem was there were quite a few guys sitting downstairs at the table not talking to anyone.

So I yell down to the group “Hey guys… If you want to come upstairs we’re doing the ice breaker activity to get to know each other!” All the guys look over and then the most awkward thing happens… really awkward…

The female bartender yells over the crowd (not hard quiet as a mouse in there) “Yeah… umm that’s what we’re doing. Getting to know each other. This is a lot more relaxed environment than that.”

My face as I said “Yeah no problem… just trying to look out”


So the quiet guys stay downstairs by themselves and we continue to chat. I answer my favorite band, movie and vacation spot. All of these are for a lot different answers and do not match the demographic of the audience. Finally, the bartender and a guy come up the stairs and ask if we want a tour. Awesome! Now is the time to start!

A guy brings us into their brewery room. It’s a large room at least three times the size of the bar area. The room is filled with barrels, silver containers (I don’t know the name of those) and other larger silver containers for mixing. Feel free to look up how to make beer on Google.  So the guy with the bartender gives us a very thorough but definitely tipsy version of how to make beer. It’s actually a great lesson… until…

Someone asks him a question about the beer at the brewery that we were visiting. He then answered “I don’t know… I don’t work here” then looks at the bartender who can answer the question. I laughed out loud. Makes sense that’s also a hot mess given the experience so far.

After the tour I go downstairs and make friendly small talk with some of the quieter guys. I don’t want anyone leaving without having spoken to someone. I talked about comic books, movies I’ve never seen, and football for a short time.

There was a cute guy that came and talked to me for a bit but I just felt so awkward and out of sorts there that I just wanted to leave. I feel kind of bad because I definitely went to the “friend zone” that I’m known for when I feel uncomfortable. He was a cute guy but I guess not for me since it didn’t go anywhere. I did give them all lessons on which apps to use to find the best ladies!

The cute guy did tell me about another dating event not put on by the website that I attended last week. I had much better luck there! Can’t wait to tell you all about it 🙂


Ever wonder what happens after the Blog? Part 1

So as you all know the dating life does not end after I write a blog about a guy. Warning what I’m about to write is not for close family or those who do not watch PG13 movies as it gets a little real 😉

Some things that are true about almost all of my blogs (I say almost as there can be an exception):

  1. I write a blog about a guy a few months after we go on our dates
  2. If I have contact information for a guy I will send him a link with the blog about him and ask for his feedback  (although very recently I’ve stopped doing this… I mean after all if you read my blog before keep reading)
  3. I keep everything PG13 (at most) as I’m not trying to be Carrie Bradshaw writing Sex in the City stories… plus I have a rep to protect. But, yes, I’m an adult figuring out the dating world so there are some not PG13 moments in  my dating life. Some of these moments are the funniest… I may get the guts to do those stories as it’s own blog.
  4. Every guy I date now knows about my blog. I’m very open about it and while it’s caused more issues than its saved…I still like to give a fair warning (Topic for a future blog for sure)
  5. I always want to stress this is my dating adventure. The guy may think differently and if he does he’s always welcome to comment.
  6. I ALWAYS change the names. Again this is my dating adventure not taking anyone else on this adventure with me 😉

Now we got those out of the way here are my updates:

Batman vs Who?… Part 1 & Batman vs Who?… Part 2

Jason* was a regular reader of my blog so I messaged him after I wrote about him. He said he was surprised that I liked him that much and that my blog was “fair” and “accurate”. The fact that he was surprised really enlightened me and helped me learn to be more upfront with my feelings with future guys. I was really happy that he thought it was accurate since he had been such an important part of my blog writing and gave me feedback after each blog post.

Since he was such a big supporter both here and in life, I refriended Jason back on Snapchat and decided to try out the “friends” thing. He was still dating the lady he chose over me and was  happy with her. After a few weeks of regularly chatting, I realized that my intentions were not the best. It’s not something that I am proud of at all and probably my biggest regret about my dating life so far.

We both kept things in the friend zone in our conversations (although I did leave the door open to a possible re connection) and I kept telling myself I could do the friends thing. It was when I ran into him and his girlfriend at a local festival that I had the stark realization that I was making a HUGE mistake still talking to him. I felt a punch to my stomach. I needed to end our friendship but that’s really tough when I thought he  hadn’t  done anything wrong.

I had a conversation with my sister (my dating reality check) and she said “Can you really just be friends Jill?” and I got to thinking. So it was then I realized that I could not be a true friend to him and already knew my place in his life. So I sent him a message. I thought he’d be surprised when I told him I didn’t have good intentions and needed to end our friendship. However, he wasn’t. He told me that he was keeping me around for “backup” for his girlfriend. That was a great lesson learned and something I realize I deserved given the situation… yeah thanks for that.



Is Two Really Better than One…

Oh Romeo*! So one of the things I did not stress enough in my initial blog was this guy  was really not kind. Yes, I’m one who tries to see the best in everyone but this guy’s date was really bad. So when he messaged me “Hello Jill” a few MONTHS after our date I was confused. I looked up the telephone number on Facebook and instantly thought “UGH”.

Now a little piece of Jill info- I do not keep numbers in my phone… at all! If it’s been like a week since I have heard from you then you’re getting deleted. I think there will be like 3 Mikes I’ll talk to over the history of my dating so why keep each of their numbers if they are history?

So Romeo messages me and I pretend not to know who he is. Yes it was a game and yes I try hard to not play games but this situation was a hot freaking mess. So I asked him who he was and he told me. Then I text something like “I’m not sure why you are messaging me? I haven’t heard from you in months and didn’t feel any connection after our second date. Judging on the time between our date and your text I’m guessing you agreed?”

He did not reply back….

Until, he found me on a dating site. He again messaged me and said “Jill, whatever happened between us?” What?! I don’t think I replied back, although I was tempted to send him the link to the blog. For everything that I wrote about there were worse things that happened that I didn’t write about. So I’m not sure where the term “us” even comes into play…. seriously dude? … yeah that’s annoying.


What Exactly am I Aiming for?

Nate*… Nate… Nate…

So I did not save Nate’s information after we stopped talking and the time that I started blogging was after our time together. So when Nate messaged me a few days after I posted my blog about him I was sure that’s why he messaged me. I didn’t know how we would have found out about my blog but it’s the internet.  I’m not going to hate on anyone that read it.

So here is a paraphrased version of our text conversation (I deleted it because I was pissed):

Him: Hey Jill! How have things been?

Me: Hey Nate! (looked him up on FB by his phone number) Wow I haven’t heard from you in forever. Things have been great! How have you been?

Him: Really good! I actually have a new girlfriend.

Me: Wow! That’s awesome! You’re a great guy I’m so happy for you. Guess what?

Him: What?

Me: I started writing a blog about dating and just wrote one about you and I.

Him: What’s the website?

Me: <insert this website>

Him: Great I’ll check it out…. So my new girlfriend, I like her a lot! She’s perfect for me! Plus she’s a total freak

Me: Oh that’s nice! Sounds right up your alley.

Him: Yes she keeps mentioning that we need to get a third person.

Me: Mmm k?

Him: I always  thought you were cool to hang out with and wanted to know if you were into that kind of thing…

Me: Yeah…you and I never had a two not sure why we’d have a three? But I’m definitely flattered.

Him for the next 5 minutes: Come on Jill! Live a little…She’s really pretty… You should give it a try.

Me: No…

About 10 minutes after this conversation he proceeds to go OFF on me about the blog.

Here are his concerns:

  • Everyone will know it’s him (My reply: How? I didn’t use your real name or anything specific about you)
  • He buys his socks at a discount store why didn’t I mention that? (My reply: I didn’t know that… hence the reason why I didn’t mention it. I can add it in if you want-  He did not seem to be amused at that comment)
  • Why I didn’t I mention how we… <insert PG13/R act here> (My reply: I’m not into the Sex and the City writing dude… but I will say he did compliment my skills 😉 Thanks Man!)
  • He’s going to comment on the bottom of the blog (My reply: No problem. Go on ahead.)
  • I need to delete the blog (My reply after a lot of consideration: No… I won’t. You’re only mad because I won’t join you and your girlfriend. You’re being ridiculous)

So the conversation started getting a little threatening… so I went ahead and blocked him. I don’t need that kind of negativity in my life… yeah that’s crazy.

Just like my entire adventure in dating so far…