Date #25.1: “High Roller”

(Note: Refer to Date #25: “High Roller” for the background to this particular date.  Also, this wasn’t exactly a date date, but it kind of turned into one…sort of.)

So during our first date, “High Roller” and I had decided to hang out the weekend following our date for some drinks and what not downtown.  I was under the impression that we were going to go to a quite/low key bar and just have a couple of drinks and enjoy each other’s presence.  Considering the fact during the last day we had agreed that we are “old” and that we prefer low-key atmospheres at times in opposed to crazy, 21-year-old filled bars, I think my assumption was fair.

On the day we were supposed to hang out, he texted me to confirm that we were still hanging out.  Honestly, I was pretty excited to hang out with him.  After our date, I was so happy to find someone who was down to just hang out and chill at a nice, quiet bar instead of getting fucked up and crazy.  Most of my friends (who I love to death, so to all of you who still party like this, don’t take this the wrong way!!) are all about just getting super drunk and crazy every weekend, so it’s refreshing to have a change of pace.  Again, being under the impression that we were just going to go to a dessert bar across from my work, I told him to just meet me at my work since I wouldn’t be off till 10pm anyways.  To this, I received a response that he was getting drunk with his friends and that he would try to stay somewhat sober by the time I got there.  While I wasn’t pissed, I was definitely a bit irritated because this meant two things: 1.) We wouldn’t be hanging out at a quiet, low-key bar that night and 2.) He’d already be fairly wasted by the time I met up with them.  Usually, when I make my mind up about how my night is going to go (either low-key or just having fun at the bars/clubs), I intend for it to go the way I had planned – I don’t like getting crazy and drinking a ton when I wanted a low-key night and vice versa.  On the occasion, it’s a nice surprise, but not that night.

So while getting ready, I had made up my mind that I wouldn’t be staying out late and that I wouldn’t be drinking very much either, because I’d rather have a couple of drinks then just head home.  I had stuff to do in the morning anyways.  So I go to meet up with “High Roller” and his friends, who just happened to be at the Oktoberfest festival.  Since I had done that the previous weekend, I was already over it.  When I got there, they were already pretty drunk and I was sober so it already sucked.  In addition to that, apparently “High Roller” had already planned out to have me drive him home, because then his friends immediately left.  So it ended up just being us two for the rest of the night.  I wanted to be closer to my car, so I made the suggestion that we meander towards the bars by my car.  Also, I wanted to visit “Boss Man” and maybe (if he was so nice…which he was) snag a complimentary drink or two.  So we walked towards the direction.  During our walk, I became really cold and “High Roller” was nice enough to give me his hoodie, even though I refused it numerous times.  He also offered to get me a cab if I didn’t want to walk since I was in stilettos.  So he definitely gets some brownie points for that.

We get to the bar and have a couple of drinks.  I’m not going to lie, by then, the only thing I wanted to do was socialize with everyone and I kind of started ignoring “High Roller”.  Not his fault by any means, but I guess he can’t keep my attention for very long….anyways, we bumped into a few people that I work with on occasion and I also chatted with “Boss Man” and his co-worker who I had met a couple of months ago for awhile as well.  I felt kind of bad for ignoring him, but I’m such a social butterfly when it comes to places like that, guys that I date just have to understand this.  Honestly, he would have been better off if he hadn’t had his friends leave him with me (they made some comment that they were leaving since I was now there, which gets me to think he had this planned out the entire time ).  Eventually I got tired and we ended up heading home.

We drove back to his place, I went pee there, and then I went home.  He tried to get me to stay, but I only live like 5 minutes away so I declined.  I did, however, promise to text him that I was okay when I got home.  And this is where things kind of got weird.  I get home, and text him, and he texts me back something about how I should have stayed to cuddle or some shit like that.  To this, I responded that I don’t like cuddling (which is somewhat true).  My phone died, but I read the next morning that he had texted me back something about how other things would make up for cuddling, which I just ignored.

*Positives: He truly is a wonderful guy and a complete gentleman for giving me his hoodie when I was cold, offering to call a cab when I didn’t want to walk in my heels, and sticking around with me when I did my social thing, but….

*Negatives: If he only has the guts to try to hit on me when he’s drunk, then that’s just not going to cut it.  Plus, he’s not as fun drunk as he is sober, and that’s just not okay.  Plus, I am still not attracted to him.  I know, no one is perfect, and I am not expecting perfection from any one person.  But all this tells me is that if I’m not willing to forgo these little nit picky things, then he’s just not the one for me.

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5 thoughts on “Date #25.1: “High Roller”

    • THANK YOU!!!! I’ve been told by so many people I know (including some of the people closest to me) that maybe I’m just not giving them enough of a chance or that maybe I should look over the small things that turn me off, but I just can’t. I’m glad you wrote this, because I completely agree!!!

  1. Just catching up with the story here… it sounds like he was trying to manipulate you into sleeping with him? Very convenient; I am glad you didn’t just fall for it and kept true to yourself. 😀

    • You know normally I would think the same thing, but I’ve known this guy for forever, and while I think he would have hoped cuddling would have lead to that, I honestly think he just wanted to cuddle hahaha. But I am also glad that I didn’t go for it, that would have turned out bad either way!!

  2. Hahaha… well he needs to work on his delivery if he wants a cuddle (sounds like you still would have said “NO”) 😀

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