Date #21: “Kooky”

How We Met:  We met through the dating website What’s Your Price.  I hadn’t been having much luck on the website, even though my last date that I met on there, “Dream Maker” was AWESOME!!  I just hadn’t been getting a lot of “winks” (as they are called) on the website and when I did, they were men from other states.  Now, as much as I would love to fly out to another state to be paid to hang out with someone, it’s still a sketchy situation.  Anyways, “Kooky” winked at me, I gave him my offer and that was that.  We discussed when we would both be available, I suggested a place, and it was set.  Initially, like almost every other date I’ve been on, I was apprehensive to go on this one.  My apprehension with this was that he was older than me…much older.  49.  Being in my mid-twenties, that’s a bit of an age gap.  Having an affinity for younger men (yes, I rob the cradle, fucking deal with it), this territory was certainly new to me.  And while the oldest guy I had ever gone for (before this date) was 12 years older than me, this was still extremely different.  Especially considering I did not meet him in person.  Anyways, yes I was interested to see what would come of it.


*Physical Aesthetics: 8 (for his age)

*Appearance: 5

*Personality: 5

*Manners: 6

*Intelligence: 5

*Confidence: I’ll say 7 but really it’s more so N/A (I really couldn’t gauge)

*Overall Rating: 5

The Date:

Since I hadn’t gone on a date in SO long (my own doing, really), I figured I should probably go out with this guy before I went on my vacation.  I really needed to pack which is why I took the night off from work, but I got most of it done pretty early so I decided to not bail on this date.  “Kooky” left the decision up to me as to where we would meet, so I had him meet me at a bar that I had really been wanting to go to for awhile.  It’s a speakeasy style bar and I just LOVE those types of bars, so I figured what better way to experience that place than with a new person!

I got there before him, so I got us a table.  And the most awkward thing happened…sitting at the table right next to me…and when I say right next to me, I mean I could hear his conversation with the person he was with, was a guy I went to high school with and traveled to Europe with in high school.  It took me a minute to realize it was him, but when I did, it was most definitely awkward.  While it takes a lot to embarrass me (I do a good job of embarrassing myself on a regular basis so it’s almost normal to me now), this situation did in the sense that the guy I was meeting up with was not only a guy I met online, but a guy who is almost twice my age.  We both acted like we didn’t recognize each other though which was wonderful.  “Kooky” finally arrived, and (thank god…maybe not, I don’t know?) he looked just like his picture on his profile.  I’ve heard so many horror stories of people not looking the same in person as they did in their profile picture, so I feel lucky to have had similar aesthetics in both profile and in person for the two people I’ve met online.

Honestly, I’ve had some really bad dates (as I’m sure you can/have read in my past posts), but this one was pretty bad.  He was a nice guy, but we had NOTHING to talk about.  There were moments where there was an awkward lull in conversation, and I literally had to think of anything I could to initiate conversation once more.  I felt that it was me doing most of the talking and him kind of just answering.  He works as the manager of a facility which deals with senior citizens with mental disabilities.  His company helps aid these disabled citizens in finding homes, jobs, etc.  This is most definitely an admirable job, but I felt that he himself could perhaps use the help he is giving to these people.  The way he spoke to me and just spoke in general was very strange…I’d say eccentric, but it was beyond that.  It was almost as if he had a mental deficiency himself.  But he did graduate from Dartmouth so I’m not too sure what to think of that either.  The conversation was very forced the entire time and we had NOTHING in common.  Basically, if I liked something, he hated it.  We talked a lot about alcohol and drinking (I’m a bartender, that shit always comes up), and he pretty much hates every alcohol I like.  I love vodka and whiskey, he likes gin.  Seriously??  Nothing in common.  I hate to blame the age gap, but I’m going to go with the probability that a lot of it has to do with him being almost twice my age.

We finally found common ground on the next bar that we went to (which ironically is the same bar/restaurant that I went to with “Almost Birthday Twin”) when we started talking sports.  While we still weren’t into the same sports (he loves football and nothing else really, I love basketball), the conversation flowed much better when talking about this.  At one point I had to pee, so I left my drink at the bar (duh).  Honestly, I was terrified he was going to roofie me (yes I can be a bit of a hypochondriac), so I set my beer up in such a way that I would know if it was touched when I got back.  And I really did think my beer moved and that he had roofied me when I got back.  But I never blacked out so I guess not?  Haha.  Anyways, the night ended about 2 1/2 hours after it started, with a nice little bonus at the end ($$$).

*Positives: He was a nice guy, he looked like what he did in his profile picture, he paid for everything (but I’m not sure if that’s a positive considering the website says they have to)

*Negatives: We have absolutely nothing in common, he’s weird as fuck, he’s old, I think he may have his own mental disability…honestly I could go on and on and on…

*Second Date?: Ya, I don’t think so.

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