Date #25: “High Roller”

Whoohoo, finally back to actual dates!!

How We Met: I met him my freshman year of college through some of the guys who lived on my floor in the dorms (these guys are now some of my closest friends).  It was our second day of living in the dorms and it was the weekend, so we all decided to go party.  Since most of us didn’t know too many people in the area, we left it up to the people who had grown up around the area to show us around.  We ended up at their friend’s (“High Roller) house a couple of blocks down the way from our dorms.  That was my very first college house party.  “High Roller” and I have stayed friends throughout the years.  At one point, I know he was somewhat interested in me, and then I accidentally lead him on (whoops, my bad) but nevertheless, we’ve been able to maintain a fairly good friendship throughout the years.


*Physical Aesthetics: 7

*Appearance: 9

*Personality: 9

*Manners: 10

*Intelligence: 8

*Confidence: 7

*Overall Rating: 10

The Date: We had been meaning to do dinner together for the longest time since, well it’s just fun to do dinners, either making dinner at someone’s house or going out for dinner.  I had been busy the past couple of weeks and so had he, and our schedules just never worked out.  But finally we found a night to do dinner!!  Since both of us were sick of our own houses, we decided to go out.  I left the decision of where to eat up to him since I’m the most indecisive person ever about anything (seriously, it’s frustrating at times).  We decided to wear dressy casual (ish) in opposed to casual or the togas we had thought about wearing earlier since he decided we were going to eat Greek.

Like a true gentleman, he came to pick me up, and even opened the door for me.  Seriously, I love that shit.  Haha.  The drive was a bit far from the area we live in, so we had a lot of time to catch up.  I’ve always known “High Roller’ to be a complete free spirit – he loves to travel spontaneously, work jobs that most wouldn’t consider “real” jobs, and really embraces the saying “Go big, or go home.”  So it was a bit surprising to hear that he recently attained a “real” job.  But he’s happy with it, so I’m happy for him.  With that being said, he also wants to be more so of an entrepreneur and start a couple of his own companies, some of which he already has ideas planned with some people.  We also talked about relationships and his recent breakup.  I liked the fact that we both kind of have the same idea on relationships – we don’t believe in the idea of having to be with the other person every single minute of every single day, or having to talk to each other that much either.  I’m all about the idea of two people coming together and sharing their lives together – not having to completely change their lives for one another, and he agrees with my thoughts on this.  It’s so nice to know that there are other people in this world who feel this same way and don’t feel the  need to smother one another in a relationship.  I thought I was the only one for a bit there.

We get to the restaurant, and the food is AMAZING.  We had this fried goat cheese thing (I forgot the name) with pita bread which was absolutely delicious.  I had the waitress pick something out for me since I normally would just go with a gyro and I wanted to try something new.  I had no complaints about the restaurant.  “High Roller” was a sweetheart and told me I could get absolutely anything I wanted for any course which was lovely.  He also took the liberty of taking the bill before I even got a chance to look at it and paid for everything with no expectations whatsoever.  Because of this though, I offered to buy drinks at the next place we went to.  We did a lot of catching up and just talking about stuff in general.  Honestly, it’s some of the best, easy going conversation I’ve had in awhile, especially on a date.  Nothing was forced and everything just flowed so smoothly.

Instead of going home after dinner and being the “old people” that we both claimed to be by going to bed early, we decided to hit up a speakeasy bar down the street (ironically, it was the same one that I went to with “Kooky”).  My experience there with “High Roller” was much more pleasant and enjoyable than it was with “Kooky”.  We sat at the bar and had our bartender make us some drinks based off of what kind of alcohol we enjoyed.  This is when we got really nerdy, and I had to point out the fact that our bartender reminded me of Luna Lovegood.  We then got to talking about Harry Potter and how much we love all the movies.  We stayed at the bar for an hour or two and just had a really good time.  I’d have to say, I think our favorite part of the night was watching one of the other bartenders make a blue blazer, since neither of us had heard of the drink, nor seen it being made.  Honestly, I could go on and on about our conversations during the night and how much fun I had, but then this would be like a million words long.  So I’ll leave it at after a couple drinks, we called it a night and he took me home.  =)

*Positives: He’s a nice guy, a total gentleman, we have a lot in common and have a lot of the same ideals, he’s nerdy (in a good way), conversation is easy, we have a few good friends in common, just a lot of fun to be with

*Negatives: He can be a bit awkward at times, he drives really slow, and of course…drum roll…I’m just not sexually attracted to him.  Seriously, something is wrong with me.  I’m beginning to think that maybe I should just give these guys I’m not sexually attracted to a chance anyways, go ahead and date them, and maybe sexual attraction will grow.  Because this shit is beginning to piss me off, and clearly I’m the one to blame.

Second Date?: Yep, most definitely!!  I think we’re going to make going out to dinner a more common thing and just try new restaurants.  Plus we agreed to stop being so anti-social and actually go out this weekend.  Maybe if I continue to go on more dates with him, I’ll eventually fall for him.  I mean shit, it’s clear he’s a great guy for me.  Plus, even my best friend “Tinky Winky Pooh Bear” has chastised me in the past for not dating him.  So yeah.

5 thoughts on “Date #25: “High Roller”

  1. Good to see what you can find. Life is learning. Food, people and new locations give us something to look for and enjoy. I like your thoughts. Life is to have fun and do something good if we can. Thank you.

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