So.....Now this "Cougar" wants to take me to Cancun over Spring Break......YOLO?

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Dec 11, 2011
A few of you may have came across my last thread about this older woman I hooked up with awhile back.
I'm in my early twenties, and shes right around 40. She's never been married, just never seemed to find the one. Anyway, I'll cut to the chase...

She's loaded basically, and I would never try to take advantage of that per se.....but I don't know what to do in this current situation. She asked me a few weeks ago what I had planned for SB. I said nothing yet. She tells me to pick a destination and we'll go......I was like well, okay....

I never told her a destination. Instead, I sent her a message saying Im not looking for anything serious, despite her being a fun, outgoing woman, etc. She understood, and just wanted to remain friends.

I was cool with it. Shes kind of a client of mine anyway, so I had to keep it on good terms. So last week she invites me to a Miami Heat game, with lower level seats. I couldnt make it.....but TODAY, she bids on this 5 Star Cancun vacation on LuxuryLink.com and she won the auction and wants me to go with her for SB.....

Do I go? Idk if Im comfortable with it. I know she dropped $1,600 on it and the spot is 
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Help?
 
You gotta go, itll just look bad if you dont. This isnt even about YOLO at this point its about her going out of her way to do a really nice thing for you.
 
Didn't even read cause I saw no pics. No excuses. What are the chances of a Nter knowing or have a cougar as a friend on FB...
 
I just don't see why you wouldn't go. It's really a win win situation for you... luxury vacation with a nice looking lady who wants to spoil you. 
You gotta learn how to play the game, son.
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Im saying YOLO 'cause its just annoying......but it somewhat holds true.
Im not posting pictures of her, too many of you are friends with me on FB and Twitter and will find a way to expose me.
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I do want to go obviously, I guess just part of me feels bad because I think part of her still thinks she can rope me in to being serious with her, which Im not having.

The resort is Secrets Capri Riviera Cancun for anyone wondering.
 
Forget Cancun and make a trip to her vag. Seems like she's been you asking for awhile. I feel like you're being oblivious and aloof.
 
Uh...I don't think she understood what you meant when you said you weren't looking for anything serious...




...cause thats a lot of money...




...but if she does see eye-to-eye with you?...and you're sure shes not trying to bait you...or guilt trip you later...





....then play ball Son!
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That being said...

...i'll be watching this thread...





BTW, where the hell do you work and what do you do for her to be a "client"? It better be worth it...

Spoiler [+]
...YOLO! 
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Originally Posted by krazy88s

Forget Cancun and make a trip to her vag. Seems like she's been you asking for awhile. I feel like you're being oblivious and aloof.

.......Been there already my man.
 
I would go. You say you already told her what it was and she's cool with it. She's 40 years old, she's probably not an idiot. She just wants to have fun and get her brains %$@$*! out by a young'n.
 
Congratulations... you got yourself a sugar mama... lucky bastard... believe you are not taking advantage of anything... its a two way street in these situations... everyone gets what they want out of it... lucky bastard...
 
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