The Most Awkward Date EVER

**Pursuit Of Love Series** Please read the intro first

The Cougar

Before dating “Erica” or what I would like to say before exclusively dating (this has a whole story for another time) her I met this “cougar” a 39 year old woman in Las Vegas. How old was I you might be asking… 22 years old. Yep a little weird but she was awesome to be around and to be quite honest one of the most interesting woman I have ever met. This is the reason I have such an attraction towards older woman, they really do a number with me with their conversation. It is BY FAR better than a younger woman’s conversation even though for example I have a 9am class and will be watching the d-backs game later, she has a 9am meeting with a client and conference calls the rest of the day( a little different in lifestyles). Back to the cougar who I will call Philly.

Like I said we met in Vegas and it didn’t really escalate into anything there, but there was definitely an attraction on both ends. Well we both went back to our home states, her being on the east coast and me being in Arizona. About 2 weeks later she all of sudden had a meeting with some friends in Arizona! I am pretty sure now looking back that was to see me, which at the time I didn’t have a clue!


The Most Awkward Moment In My Life!


She came out to Arizona and the first night we hung out and it was a great time, we a lot of fun and that attraction was still obviously there. We went our separate ways that night but we talked about going out the following night. She calls me that 2nd night and casually says we are going to dinner with some of her friends and she mentions we are meeting at the Phoenician which is a high end hotel in Phoenix. I didn’t really think about it too much, I already met some of her friends from Arizona before.


I was meeting her and her “friends” at one of the restaurants at the hotel. I am going up the elevator to the restaurant and I start realizing, who am I exactly meeting her with??? Well I arrive and I see her and her “friends” which I realize right there it is a DOUBLE DATE, which that is fine. I get a little closer and realize these other people I am sitting here with are at least in their 60’s! THEIR SIXTIES!!!!! At this table there is a 22 year old, 39 year old, and two 60 year olds! You want to talk about weird moments in life, to this day I will not forget that moment. For the next FIVE hours the 4 of us had just a great time (sarcasm). I could not imagine how weird it must of been for them but I just started drinking and the nerves calmed a bit, I mean I did have a lot in common with the 60 year olds kids (and yes their kids were older than me)!

Talk about a night!


Stay tuned next Friday!


Pursuit Of Love Series

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The Pursuit Of Love

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