Dating Diary: From the Worst to the Best

Profile of a woman in her fifties, and her dating diary of experiences from worst to best!

The Ugly

I had a hunch it wasn’t going to go well after I agreed to meet him and he said, “I don’t know

what I’m going to wear.

 

He said It’s going to depend on how I’m feeling” and my first thought was,

”Great, this guy isn’t even going to try and impress me.”

 

I mean, it’s a first date, right? Don’t you want to put your best foot forward? Not this guy

apparently.

 

The day of the date I texted him to confirm the meeting time. At 5:09 he responds with “on my

way now, 5:30.  At 5:26 he tells me he’s 10 min away. At 5:46 I get “Traffic sucks”.

 

I responded with “Sorry. The margarita is tasty!”

This suave, debonair man responds with “But ru lol”.

 

Gross. I could feel the bile rising in my throat from his inappropriate comment.

He finally walks in 40 minutes late as I’m finishing my margarita. I was about to get the check

and leave. Since he walked in, I ordered another one. He ordered a Guinness.

We start talking, and I notice he’s missing teeth. One on the bottom middle, and at least 3 more

on top middle and to the right.

 

I mean, no teeth? It’s 2022. You’re an adult. Go to the dentist.

 

A bit later he says “did you see my text?” with a big toothless grin and 13-year-old giggle. I

feigned ignorance and looked at my phone. “Oh.” and gave him what I perceived to be a look of

“Seriously?”

 

I’m getting tired, and I share that with him. A few minutes later I announce I’m going to go home

and get some sleep. “It’s been a couple of very long days…”

 

So, he waves down the bartender to get the check. When the bartender returns, he pulls out a

$20 and tells the bartender “That’s for the Guinness”. That’s right. He didn’t even pick up the

check. I added my credit card to the tab and waited somewhat impatiently while the bartender

went to ring it up.

 

While we’re waiting he asks “Would you like to get together again?”

“I’m not feeling it.”

 

I mean seriously. 40 minutes late. Lack of teeth. And he didn’t pick up the tab. No, there’s no

way I’m going out with him again.

 

The Okay

There was a man I connected with on a dating app months ago. He seemed nice and we even

talked on the phone, but we never got around to making plans. A few months later, we

reconnected, and at first, I didn’t realize it was him! We exchanged numbers and the previous

chat came up, reminding me who he was.

 

Rick is a police officer in a county nearby, and the one thing that stuck out about him, was that

he liked to find a place to “hide” while on the job. Our tax dollars hard at work! That said, I totally

respect law enforcement and I realize they deal with a lot of crap that most of us can’t even

imagine, so if he’s hiding, I have faith that when he’s needed, he’s THERE.

Anyway…

 

Rick lives in the same town as I do, so when he suggested a place to meet for breakfast that

was 30 minutes away, I was taken off guard. He offered to pick me up, but I don’t get into

vehicles with people I’ve never met before. I politely declined and said I would meet him there.

 

The front of the restaurant was your typical breakfast type place, with counter service and

tables. The back of the restaurant was more interesting. We walked through a gate, which were

the old iron bars of a jail cell, including the door, complete with the lock still intact. The walls of

the dining area looked like the outside of an old barn, with a wagon wheel adding to the decor

as well.

 

Coffee, coffee and more coffee! When the waitress said they make their pancake batter from

scratch I of course had to order some! Oh My God… So tasty! It was definitely worth the 30 min

drive to get there.

 

Rick and I had a pleasant conversation and the time passed quickly. He’s a really nice guy and

had fun stories to tell. I could definitely see myself going out with him again. We finished our

meals and he walked me to my car. He said “Let me know if you want to go out again” I told him

yes, and we had a nice kiss goodbye.

 

Rick loves to cook and he was cooking for friends that afternoon. He sent me a picture of one of

his finished meals and I replied “Yummy!”

 

I’m not sure why, but I haven’t heard from him since. Nice guy, but if he wants me, he needs to

work a bit harder than that.

 

The Good

Gene is a super nice guy. We met about noon at a cocktail bar on a sunny Saturday. There was

an event going on outside with live music. We went under a tent to get out of the sun, and to try

and get away from the music because it was just too loud. After a bit we decided it was also too

hot, so we found a table inside.

 

Bloody Mary’s were the cocktail of choice this afternoon and I have to say, it was the first time I

ever had one I enjoyed. The last time I had one there was so much crap in it, it wasn’t good.

These Bloody Mary’s were exceptional and they are now on my to- drink list!

 

The conversation with Gene flowed easily. A down to earth man’s man, he’s into dirt bike racing,

fixing cars, and taking care of his family. He even explained to me how his daughter, who is now

in her 30’s, reached out to him when she was very upset. She had just found out she had genital

herpes.

 

I do believe my jaw dropped at this point. I looked at him and said – “Your daughter would have

a stroke if she knew you just told a woman on a first date that she has herpes!” He instantly

turned red, realizing he probably should not have shared that.

 

Aside from his faux pas, we had a good time and a good rapport. We dated for a bit but in the

end we discovered we weren’t compatible. We’re still friends though!

 

 

The Best

What was probably intended as a “we should do this” type of comment, turned into a first date.

 

Ben and I had been chatting and we decided to go white water tubing. He was shocked I agreed

to it. I had told a friend of mine and my friend was like “On a first date?” I told him “Hey, if I’m

going to date him, he’s going to see my body eventually. He’ll either like what he sees, or it’ll

eliminate him really quickly. And I still get to cross tuning off my bucket list!”

 

It was the best date I’ve ever had! Although it didn’t start off that way.

I was at the gas station when he called me.

“What do you want to drink?”

“Miller Lite”

“Really?” He sounded surprised.

 

I said “Yes. Really.” I asked him later and he told me most women he knows want to drink wine

or seltzers. For me, wine is a memory eraser. I enjoy seltzers, but whatever sweetener they use

gives me a headache so I’ve stayed away from them.

 

I continued to gas up my car and got on the road to meet him.

It was about a 45 minute drive for me, and about an hour for him. I got there close to on time,

but Ben was stuck in traffic. He kept texting me letting me know his progress, so I knew he

wasn’t full of crap.

 

He finally arrived about an hour later with a 12 pack of miller lite, and frustrated from his drive,

but also relieved that I was understanding. I mean, we’re driving on single lane roads and you

get behind someone taking their sweet time, I get his frustration!

 

I had never been river tubing before, and if you haven’t either, here’s how it works.

They gather everyone on the trip under a tent, give you safety rules and then you wait for a bus

to come pick you up and drive you to a drop off point at the river.

There are no guides for this. They give you a life vest and a tube. The rest is up to you.

Ben was thinking ahead of time and remembered to get us a cooler float for our cooler, and they

gave us twine so we could tie ourselves together.

 

We got on the bus. The bus reminded me of the bus I took to school as a kid. We’re talking

1970’s era school bus, with small seats, no seat belts and no air conditioning.

Everyone on the bus had their life vests on. I am still baffled as to why you would put the vest on

for a bus ride. They are big and bulky and not comfortable, but Ben and I were the only ones

who seemed to realize you need the vest for the river – not for the bus!

 

To add to the no air-conditioning fun, there was an odor wafting in our direction. It was hot, and

there was one unidentifiable person we could smell. Both Ben and I kept checking under our

arms to make sure it wasn’t either of us! A stinky first date is NOT sexy!

 

We reached the drop off point about 20 minutes later. We stayed at the back letting everyone

else go in front of us. As we approached some steps there was a woman in front of us who was

caught up in something – maybe the twine that was attached to her tube? I honestly can’t

remember. What I do remember is the smell. The stinky person was no longer unidentifiable…

We got as far away as we could as we launched into the water.

 

I had never been river tubing before. We tied ourselves tubes and cooler raft together and

slowly floated down the Potomac. I had my vest on by this point, but I wanted sun so I left it

unbuckled. Ben – he went vest-less. I kept giving him a hard time about not wearing the life vest,

but he didn’t care! “I’m a strong swimmer. I used to train by swimming in riptides.”

I rolled my eyes, reached into the cooler and cracked open a beer.

 

Despite his lack of water safety, this was by far the coolest date I had ever been on. It was such

a unique experience. We chatted as we floated down the river. We talked about kids, the stinky

lady from the bus, and how I surprised him when I told him I wanted to drink Miller Lite.

 

Apparently, he expected me to say seltzer or wine. I never claimed to be your average woman.

We reached a point on the trip where there was a 2-3 foot drop off over the rocks. YIKES! And

the current was pulling us in that direction.

 

Try as I might to go the other way I finally realized we weren’t getting away from it. I went over first, he, and the cooler went over next. I fell off the tube and was able to get to my tube. I turned around just as I popped back up to the surface, one hand still holding the cooler above the water line. The cooler wasn’t just holding the beer.  It also had our shirts and our phones, which I had placed in a plastic baggy at the beginning of the trip.  Ben managed to get back in the tube, still sans life vest. He lost his ball cap, and a beer koozie, but we managed to hold onto all the really important items.

 

The rest of the trip was less eventful, and we finally made it to the pick-up spot at the side of the

river. We were among the first there from our original bus load. We got on the back of the trailer

and a truck hauled about 25 of us up the hill onto the property.

 

I have to say, if you ever get the opportunity to do something this unique- DO IT! Experiences

are much more fun than sitting across each other searching for small talk in a bar.

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