So this blog may feel more like random dating updates put together than one cohesive blog. Please follow me along on this journey I’m not sure where it is going but we will see.

First Update:

I went on a date a few weeks ago! I am not sure why the exclamation point as it was more of a . date. I met this guy when I went back to Hinge for 3 days. Yes a total of 3 days.

We had matched on a Tuesday night. Wednesday morning we are flying fingers texting back and forth. He is engaging and I find myself wanting to text back and forth. He kept me “virtual” company while I got my oil changed and a new tire. Our conversations on the gourmet coffee at the Jiffy Lube was something for the books.

So when he offered to join me in a cup of the fancy a cup of joe I was interested. I liked that he didn’t waste time. However, my tire was almost done so I suggested a brunch afterward at the sexiest place I could think of…. Cracker Barrel.

I had warned guy that I was dressed for a tire change not a date. Jeans and a sweater. Hair in a pony and absolutely not a stitch of makeup. He said he was into it. So was I… this is more my normal look.

About an hour (and $200) later I pull up to Cracker Barrel. As pumped as I was to meet the guy, I was more excited to take a first step out of my Weird Place.

I show up earlier than he does. I grab us a table and jokingly tell the hostess “If he looks like your usual clientele (elderly) bring him to another table.” She laughed.

I see him walking towards my table. He looks a little older than his pics and apparently I wasn’t nailing it out of the ballpark either.

His face spelled D.I.S.A.P.P.O.I.N.T.M.E.N.T. I thought “this is going to be awkward.” … I had no idea.

Now to anyone that thinks “oh poor Jill!”

I really don’t mind. If I have learned anything during my life in dating, it is chemistry and attraction aren’t personal. Everyone has different preferences and there have been great men I’ve passed on after a date. Again no biggie.

So seeing his face I realize I need to really play up the friends feels. It was harder than even that…

Actual excerpt from our date (as I remember):

So you travel about an hour for school! Do you have any favorite podcasts?

No.

What do you do during the drive then?

Music.

Oh yes I love music too! What do you listen too?

The radio.

Like what stations? Country, Rock, Rap?

I switch stations.

Yeah I love variety too!

Now, about midway this interaction I started playing a game. Can I get him to say more than 1 word answers? Clearly I won by the end. 3 words. 😂

To accentuate the friends feel I even brought in such gems like:

What age range are you looking to date? In case I have any friends.

You know sometimes it doesn’t connect but it is nice to meet new people.

He did budge a little. Maybe a 10 word answer at some point.

I eat my lunch quickly and ask for the checks. I am being super friendly throughout both because I LOVE awkward situations and because I’m going to have fun either way. His experience isn’t going to determine mine.

By the end it is a quick wave as I finish paying and he’s checking out. Glad I went out through.

Second Update:

I was driving through my hometown at night. My kid and I wanted to take the backroads to my sister’s house. The small town had decorated for the Christmas holiday with white lights and garland! It was perfect! As I’m almost through the downtown I see HIM.

Yep…Jack…

He didn’t see me but about 10 feet away is him and his kids.

Do you know that flash of tingles you get in your head when you almost get in a car accident? The rush of adrenaline? That’s what happened. Just as quickly and involuntary but started in my chest.

I told my kid and we quickly changed the playlist from my teaching her Eric Clapton to our mutual love of rap music. It was needed.

Third Update:

Last week, I also ran into a single date past guy. Aaron!

At first when I had seen him I was deep in thought so when he said hi I just did a half wave and kept walking. As I was walking I thought “Dang that’s Aaron!”

I decided to play it cool. I didn’t go back and just ordered a drink. Yes something I’m not good at….

After about 2 hours (or more realistically 20 minutes) I ask a few guys in the group to play a Simpsons bowling game by where he was. I decided if he wanted to chat he could come to me. Which after a little wave he did! 😍

We then talked for quite a while and various times throughout the night. He was even hotter and funnier than I remembered. At the end of the night I gave him a hug.

Then that’s when I stopped playing cool. I messaged him for another date. Yeah I probably shouldn’t have since he turned me down the first time. But patience has never been my strong trait.

After a few messages he didn’t really answer. Oh well. I’ll learn to be more Chilly Jilly someday, or more realistically, I’ll find someone that finds it endearing and cute. I have a lot of things to work on I can’t focus on everything. *I tell myself*

Fourth Update:

May have something brewing in my dating life with a local radio show! We will see and if it is exciting there will be more details to come. 😘

Overall a lot of little moments that show progress in my weird place feelings but no big moments. Don’t worry though I’ll let you know when one is coming ❤️