Dating…round 1!

I usually don’t get too personal on here, or share legitamate thoughts or concerns. A recent interest of mine has requested I write a post about him, so here it goes: 

Recently, I decided to dive into the dating world, basically head first. I installed all of these apps on my phone that can be used for dating, among other things, and opened up a few online profiles. I’ve also told a few friends I’d be interested in going on blind dates and doing speed dating. The speed dating would be mainly for the experience. I’m a pretty shy guy the 1st 3 dates, so I have to squeeze a date into 8 minutes?!? I hope my smile, style and a drink gets me a second date.
Anyway, my inbox received a ton of messages, “smiles”, “winks”, and “woofs” from a variety of guys. I always replied with at least a thank you to let them know I was appreciative of their compliments, but after that conversation was not garuanteed. I did switch phone numbers with people, met a couple for dinner, but not too many were really tickling my fancy. 
Well now that I’ve set the stage. I guess let me tell you about the one who requested this post. I shall name him Sargent Simpleman. We actually met online 2 years ago, and after a few weeks of chatting online and through text we finally met for ice cream. It was the 2nd weirdest date I had ever been on-I think. Now, obviously online dating can be a little scary and you never know truly what you’re getting yourself into, but to me that’s the thrill of it all. I just make sure I’m safe-let someone know where I’m going, what he says his name is with a pic and meet in public.
He obviously didn’t believe in this philosophy because he knew my whole life story from Google before we even got together. I was quite astonished at 1st, and after I calmed down, I realized I was more surprised that he did it and used what he found to carry a conversation. So I put a point in his con jar for ridiculously nosey. 
We sat outside and talked for 4 hours that night! Most would agree that’s a good date, however, I left feeling not so sure. The convo had it’s ups and downs, but I left feeling he was really nosey, intimidated by me and a bit of a challenge/project (my favorite). Needless to say, nothing for 2 years! 
Here we are 2 years later and neither of us have changed much. He is still claims to be a stubborn guy that hates most social situations. I am still me, the single spoiled hopeless romantic with jerk tendencies, yet is mainly go with the flow. 
We’ve gone out twice and have some future dates planned, but I’m pretty sure I have him figured out. He is picky and can come across as a jerk, but seems to have a descent heart.
Tonight, we went out on our second (or 3rd depending on if you count the one from 2 years ago) date. He was just getting into town from a family trip to Tennessee and was sooo “cranky and tired” and was exuding all of this negative energy through text. Once he got to the restaurant, he smiled. He complained a lot (nothing new) but he wasn’t in a bad mood and I’m quite happy my presence changed that (so, I’d like to think) because I would not have been a happy camper had he been in a bad mood. The rule of thumb: if [Mr J Sully] ain’t happy, nobody’s happy.
He’s been so worried about me handling his bad moods and pickiness. I wonder if he can handle mine (cupcakes, chocolate, wine, etc usually helps, just sayin’)
No pics yet, probably gonna have to wear him down on that. 
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