This are parts 2 and 3 of my first experience with an older man.
I am reconstructing my story from my diary, emails, texts and memory. Granted, I may be romanticizing things, but this is how I remember it. The conversational parts are obviously paraphrased.

-Red

After that encounter, I was left overwhelmed and indecisive, but I couldn't deny that I wanted more. Figuring out how to make contact with him became a mental maze. Should I text him? Should I call? And then the doubts crept in: What if he was married, with kids, living in some perfect suburban home? Those thoughts swirled in my mind, but they didn't stop me from "fantasizing" furiously about what it would be like to be with him. What kind of man was he? Sure, my experience was minimal, but I'd read my share of erotic stories and watched some porn, though I always preferred reading. Porn felt too blunt, if that makes any sense.

More than two weeks passed, and I still couldn't bring myself to dial that number or even draft a message. What would I even say? "Hey, it's the nervous redhead from the coffee shop"? What if he replied with, "Which one?" Maybe that was his thing, picking up girls at coffee shops. What if all he wanted was a quick fling? My mom's voice echoed in my head, calling it "my flower" and warning me "that's all men want". I was a bundle of nerves, torn between wanting to move on but then my brain would chime in, "Move on to what? Hoping another stranger makes a move, because you sure as hell aren’t going to."

I tried convincing myself to let it go, but I couldn't bring myself to toss out that slip of paper with his number on it. Sometimes, after a particularly steamy moment alone, I'd look at that paper and think it might just be a keepsake—a reminder of that intense encounter.

The only time I managed to stop obsessing over this was during school and work; outside of that, my mind was constantly at war with itself. Realistically, I had been sheltered my whole life, with minimal experience with men. I was shy and struggled socially. My only friend literally fucked me and vanished. Social interactions were rare, mostly confined to my part-time job. Otherwise, like most people my age, I found solace in online interactions. Funny how that's exactly what I'm doing now, isn't it?

One day, I had such a great day at work and school, feeling good overall. I remember thinking, "I wish every day could be like this!" Anyway, I told myself, "Okay! Today's the day I'll text him." Then my mind raced: "What if he wants to meet today?" He was clear he wasn't interested in just being friends, so reaching out meant I was agreeing to see him differently, right? Before I could talk myself out of it, I sat on my bed and after a few ridiculous drafts, finally wrote the perfect message. In quiet moments, I still look at our texts... I'll probably delete them one day, but not today. It said, "It's REDiance from the coffee shop. I hope this isn't too forward, but I've been thinking about our conversation and your offer to keep in touch. Are you still up for that? 😊".

And then I hit SEND.

Right after hitting send, I started second-guessing myself: "That was such a dumb message. He's probably thinking 'LOSER' now when he reads it... SHIT SHIT SHIT." I obsessed over it, reading and re-reading, thinking of all the better things I could've said.

After what felt like waiting through two eternities without a reply, I gave up and felt totally rejected, like the biggest loser. I just flopped down on my bed and moped. I thought about sending a lame excuse like "oops, wrong person!" but let's be real, that would've sealed my fate as "loser of the year." So, I just sighed and lay there, phone next to me, clinging to hope.

Then, "DING," I got a message. I was dying to check it, but I also didn't want it to be a letdown from mom, dad, or work. So, I took my sweet time, staring at the screen, hesitant.

Finally, after enough delay, I glanced at my phone. It was a message from him!!!

As I picked up my phone to read the message, it said, "Hello Ms. REDiance, I’m so pleased you decided to take me up on my offer to stay in touch. How have you been?"

So casual, as if I hadn’t been mortified the last few weeks trying to figure out if I should reach out to him, right? I have to admit, I was relieved to see that he wasn’t put off by my message and thinking I was some sort of loser.

Of course, I obsessed over what to reply. I finally decided to be funny. If he could be direct, why shouldn’t I be funny? So I said, "I'm good, a little busy, but I thought I’d send you a message to see how you were doing. I’m still interested in being friends... lol".

His response was a bit more direct than mine. He said, "I'm doing well, thank you for asking. I appreciate you reaching out, but I want to be clear that I'm looking for something more than just friendship. If that's something you're open to exploring, I'd love to get to know you better. Are you open to exploring this?"

I thought to myself, "Jesus, learn to take a joke!" But there was a part of me that was impressed by his lack of interest in mundane humor and his ability to stay on track with what he wanted. This would've killed with a younger guy.

Again, putting me under pressure... but I liked it. I decided to match his directness and sent a message saying, "Are you married?" Jesus! I was so nervous! What if he said "Yes"? Was I ready to be "the other woman"? What if we really hit it off? Was I ready to be a home wrecker? What was I thinking? Of course, he was married! Why else would he be interested in someone like me?!

Now, it was a matter of waiting. I figured it was my turn to turn the tables and put him under pressure. Surely, he would fold.

I figured it would take him a while to respond; after all, he was married. He'd have to come up with a good story like "yes, but we're only together for the kids" or some variation of that, just like my mother said in her "life lessons".

As you might have guessed, he responded right away, saying, "I asked if you're interested? If you're interested, then it won't matter".

Now, I knew no matter what I said, he would come back with, "Are you interested?" So, I said, "Yes, I am interested." I mean, I obviously was, so I might as well come clean.

I remember thinking to myself, "Here comes the bullshit."

His response was, "No, I am not married. What are you looking to get out of this relationship?" WHAT??? He managed to put ME on the spot again? How the fuck did he do that?

If I asked, "What are YOU looking to get out of this?" surely he would see right through it and know I didn't have a real answer. His directness had cornered me into really thinking about things. This was so much easier with younger guys online; I could bend them to my will so easily.

Alright, I decided honesty was the best policy, so I went for it and said, "I really don't know, but I am intrigued".

His response was "Good girl. Honesty is always best. As long as you're honest with me, I have something to work with." How the hell did he know what I was thinking? Then I remembered "ah! older guys, they've heard it all before"... But why did it feel good when he said "good girl"? For some reason, I felt rewarded by his approval. I remember thinking "holy shit... am i one of those??"...

Anyway, now I was even more intrigued than before, I asked him "what are YOU looking to get out of this?".

His response was a simple "Let's get together for dinner, or coffee, and we can talk about all this while getting to know one another. This conversation will be much better in person, don't you think?".

This guy moved fast and made all my anxieties flair up, but also made me excited and curious at the same time. I honestly did not know what to do. Going out with him was something that was nerve-wracking for me, not only was I not used to face-to-face interactions with men, but he was so direct. I was not ready for that.

Again, I opted to be honest, that seemed to work with him and I was starting to realize that I felt good after being honest with him, so I went for it and said "Honestly, I am still very nervous about this whole thing. I definitely would like to get to know you better, but this is going a lot faster than I am used to".

He responded very quickly saying "I understand your angst, but I also know that the best things in life come unexpectedly and usually after a moment of discomfort. I certainly want to make sure you're comfortable when we meet again, but I also want to make sure we don't miss any opportunities we have to get to know one another".

As I read the message, I kept thinking that he sounded understanding, but not without expressing his thoughts and desires... I liked that. As I was still processing that message, another message from him came in saying "Here is what we can do, I have to go out of town for a few days, why don't we make plans to meet when I come back?". "Ding" another message saying "Of course that is with the understanding that if you're still not comfortable, then you can let me know and we'll decide what happens then. Is this something that you can work with?".

Again, he sounded very understanding and it felt as if he was trying to take some pressure off of me, which was a welcomed change to what I was used to. I decided to be funny and sent him a "challenge accepted" meme, you know the one. However, there was no response... I waited 15 minutes, nothing... 30 minutes, nothing... after an hour of waiting, I decided to send another message saying "That sounds like something I can live with". He immediately responded "sounds like a great plan. I am looking forward to our first date!"

And that was the end of that interaction, but I was left with more questions: Why was he going out of town? Was it work? What did he do for a living? I also wondered what did he mean by saying "we'll decide what happens then" if I decided not to meet him when he came back? Did it mean he was going to continue dealing with my indecisiveness, or was he going to say "to hell with this, I have many other women waiting in line!"?

Yes, I tend to overthink things...

to be continued...