The Text Me Tomorrow Guy

Photo by Andrea Piacquadio on

After all of the back and forth and up and down emotions that filled my relationship with Matt, I took a much needed break from dating for a bit. I’ve come to realize that this is all part of the cycle of dating for so long. Every now and then when it gets too overwhelming, it’s best to take a break and reset so I can put my best foot forward towards trying to find Mr. Right.

So back on Match again where I’ve often felt I had the best success with dating, I find myself chatting with Sean. He seems like a nice guy. Nothing blowing me out of the water about him, but no red flags jumping out either. Our messages were flowing pretty quickly when Sean suggested a date, and I was more than happy to meet him and see how things would click. Of course, he had to suggest meeting for dinner or lunch causing me to break my first date rule. And we ended up at the same restaurant where things went terribly before with The Awkward Turtle guy so maybe this one was just doomed from the start?

I think this story is best read as it happened. I’ll provide a little commentary as we go, but I think it’s pretty clear why things didn’t work out with this guy.

But before we’ve even had the chance to meet, he hits me up with this lovely question.

After asking if I would be available to text after getting home from an event for school, I had to gently decline that invitation. Remember we haven’t even made it to our first date yet.

And true to his word, he doesn’t wait for me to text him, but instead he’s right there again in my message inbox.

Luckily, the weekend finally arrives and we finish making plans for our date.

This guy has slowly started to exhaust me with his daily texting before even meeting, but I tried to keep a good attitude about the whole thing. At least this time I knew he was there and wasn’t running around the restaurant asking random guys if they were my date.

We had a relatively decent date. The conversation flowed well enough through the awkward first date nerves, and we had a few things in common like both being teachers and enjoying sports. There certainly weren’t any sparks flying yet, but I wasn’t completely turned off either. Of course, Sean checked in by text practically before I even had time to make it home.

I can already feel myself starting to pull away after this awkward revelation about him wanting to hug me. And apparently I didn’t respond to his text fast enough.

But of course before I can text him, he’s back again.

He’s insistent about planning our next date so I throw out some suggestions and a little jab to hopefully playfully make him realize he’s starting to drive me a bit crazy.

Again with the incessant need to ask me to text him. What is with this guy? And a picture this time too in case I forgot what he looked like. But I’m sure you can guess that he messaged me again before I even had a chance to do it first. Of course he did! Even though we have another date already set up, he’s still trying to get me to meet him sooner because I’m apparently so amazing he just can’t wait to see me again. This guy is really starting to get on my nerves when our next conversation leaves me completely flabbergasted.

Did this dude really forget my name, and then think I gave a fake name on my dating profile? Cue facepalm.

We finally make it to our next date. The plan was to go bowling, but then we ran into a bit of a problem. First of all, I got a text from Sean that he was already there 30 minutes before our date was supposed to begin. Then he informed me that a private party had the whole place rented for the afternoon.

We pivoted our date to a nearby brewery. Not quite as much fun as getting into an activity, but a place with good beer and good vibes. I again had a nice time, but by now I could tell that this was really not the relationship I was looking for. The guy could barely go 24 hours without texting me, and it got on my nerves so much I don’t think he even left me enough space to decide if I might have been interested in more with him. As we ended the date, I had to deal with the reality that I needed to let this guy know how I felt asap before he got more into me.

What I should have said is only 4 times? That’s really not so bad. Come back and talk to me again when you’ve been trying stupid online dating for 4 years or more and still not having much luck. So I left Sean heartbroken after only two dates, and I was no closer to finding love myself. But at least I wasn’t desperate enough to settle for this stage 5 clinger.

Until next time,


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