Impressing (Hot) Older Women
 

I recently met an incredibly beautiful single older woman through my good friend's fiance. I was invited to my friend's engagement party at this woman's house last weekend. Before the party all I knew about her was that she has been divorced for at least 3 years, is 41 years old, drives a Benz, has a vacation house with two boats and also a big "main" house with a pool just outside the city, has a 19 y/o daughter, and has had horrible luck with men lately and was actively looking for a "good one".

I was also warned that she was attractive, but I was way underestimating it. She is a 9 in my book, can't imagine anyone else rating her lower than an 8. She looks like Demi Moore from about 6-7 years ago, accept bigger breasts (large Cs) and she is latino.

It happened to turn out that I was the only single guy at the party, so that worked out pretty well for me. I talked and flirted with her the whole night as often as I could without making it seem obvious, and was getting it back just the same. She was playing hostess so it was difficult to get her alone, and my plan at the end of the night to be there after everyone else left failed.

I left the night figuring it was just a fun night flirting with an incredibly hot woman. Well, today I find out from my friend that she thought I was great and wants to hang out with me again soon. Apparently the two girls are planning a scuba diving trip double date for some weekend soon.

Honestly I am wondering why this woman is interested in me. She is way hotter than me (I'm average looking at best), and she is already rich. Plus the 14 year age gap (I'm 27) and her having a 19 year old daughter. Whatever the reason, I don't want to screw this up. Any suggestions on how to make a good impression on her? What could she be looking for in me?

Cliff Notes:

I (27 y/o avg looking) met and flirted with an incredibly hot 41 year old divorced mom (with some nice bank) at a casual party. To my surprise she wants to hang out with me, how do I not screw this up?




She looks very similar to this picture accept less makeup

http://www.librarising.com/astrology.../demimoore.jpg

Re: Impressing (Hot) Older Women
 

First off 41 yr. olds don't "Hang out". So strike that from your vocabulary. Secondly, she just wants cougar sex. Give it to her. Don't expect anything long term. Just enjoy.

Re: Impressing (Hot) Older Women
 

be yourself and dont try too hard. just be funny and flirtaceous and slightly challenging to her but not too much so

seem genuinely interested in her stories, etc etc

*edit* if she hints at basic cougar sex just go with it and let her make you however she wants and just go along with it :P

Re: Impressing (Hot) Older Women
 

This sounds like a problem I'd like to have.

Re: Impressing (Hot) Older Women
 

Either she's into you or she's not. You're not going to magically change her mind with some gimmick like dressing up like Mr. Peanut.

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
You're not going to magically change her mind with some gimmick like dressing up like Mr. Peanut.

[/ QUOTE ]

OP should totally do this.

Re: Impressing (Hot) Older Women
 

Just mentally prepare yourself to deal with major league psychosis in exchange for serious hardcore. Lots of listening and not too much talking. Also, be sure to capitalize on the ego and image boost by parlaying your increased confidence into more poon.

Enjoy the ride.

*edit* Just noticed that several others essentially said the same thing. Nevertheless, my Grunching should reinforce the accuracy of this advice.

Re: Impressing (Hot) Older Women
 

Maybe she just likes you for you! She's probably screwed heaps of hot guys, rich guys, maybe even hot rich guys.

Do any cougar hunters agree with my theory?

Re: Impressing (Hot) Older Women
 

I don't normally grammar-police, accept you did it twice in the exact same context.

Re: Impressing (Hot) Older Women
 

Just be yourself. Any game she will see through instantly.

Re: Impressing (Hot) Older Women
 

Cook her dinner at your place. From the sound of it, she would be easy to impress with a nice dinner and a few bottles of wine. Plus, she gets away from the kids, and it's easier to transition to the action.

Be careful not to "plan ahead" too much. A lot of guys will be like, "let's do this and this and this" after meeting a girl only a few times and they feel controlled. Good Luck!

Re: Impressing (Hot) Older Women
 

Tell her a story that begins with "so the other day after I jerked off for the sixth time..."

Re: Impressing (Hot) Older Women
 

If you want to impress her send her a picture of Grimstarr saying it was you in high school

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
She looks like Demi Kutcher from about 6-7 years ago, accept bigger breasts (large Cs) and she is latino.


[/ QUOTE ]

Impress her with your bedroom skills.

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
[ QUOTE ]
[ QUOTE ]
She looks like Demi Kutcher from about 6-7 years ago, accept bigger breasts (large Cs) and she is latino.


[/ QUOTE ]

This is true.

Maybe she just likes you for you! She's probably screwed heaps of hot guys, rich guys, maybe even hot rich guys.

[/ QUOTE ]

And so is this.

Impress her with your bedroom skills.

[/ QUOTE ]


And like several others have said, sit back and enjoy the ride.

Re: Impressing (Hot) Older Women
 

pics

Re: Impressing (Hot) Older Women
 

Mr Peanut does sound like the best strategy.

Re: Impressing (Hot) Older Women
 

I can tell you only one thing: there is nothing you can do to artificially impress this chick. She's been around a lot longer than you, she will be able to see through any act that you put on and will most probably think you're a dick for pulling one. If she already likes you then all you have to do is be cool and let her keep liking you. Be very laid back on this. You won't be in a relationship with her, you'll just be having a good time and enjoying each others company.

Let us know how badly you feck it up.

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
I can tell you only one thing: there is nothing you can do to artificially impress this chick. She's been around a lot longer than you, she will be able to see through any act that you put on and will most probably think you're a dick for pulling one. If she already likes you then all you have to do is be cool and let her keep liking you. Be very laid back on this. You won't be in a relationship with her, you'll just be having a good time and enjoying each others company.

Let us know how badly you feck it up.

[/ QUOTE ]

qft. just play it by her rules. There are way too many ways to [censored] up here otherwise.

Re: Impressing (Hot) Older Women
 

Go with the flow...Be interesting/intersted in what she has to say !

Obv, you have the foot in the door, you have friends trying to get you into the same "situations"...Just be yourself....You're probably different to want she has had before so no pint trying to be something you're not..

And great call and the planning ahead thing.....Don't do that under any circumstances...

Re: Impressing (Hot) Older Women
 

being an almost cougar, trust me, she likes you. period. It's all fun, be very sweet, and enjoy yourself..incl the intelligent & funny part too..few glasses of wine, and make a little move...not toooooo much...then your off to the races [img]/images/graemlins/smile.gif[/img]
don't forget TR!!!!!!

-ala

Re: Impressing (Hot) Older Women
 

women are interested in:

money
your social status
your personality
your looks

so it sounds like you better do a lot of work on personality.

Re: Impressing (Hot) Older Women
 

"she has been divorced for at least 3 years, is 41 years old, drives a Benz, has a vacation house with two boats and also a big "main" house with a pool just outside the city, has a 19 y/o daughter, and has had horrible luck with men lately and was actively looking for a "good one"."

so she is a rich gold digger who has had bad luck with men? lol

Re: Impressing (Hot) Older Women
 

lebow,
dude you are soooooooooooooo wrong about older women liking younger guys...
damn, your list is of what younger women want in a man. Established women want good company and great sex. older men seem to suck at both of these.

Re: Impressing (Hot) Older Women
 

OP,

If you have any thoughts about Powerball numbers this week, please send a PM.

Re: Impressing (Hot) Older Women
 

from a guy who dates an older woman. She never cared waht my age was she was more interested in that I was a good person and had a decent job and wasnt a pyscho . pretty much a requirement for myself. Younger women seem to be to flighty and material. They also suck in the sack compared

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
women are interested in:

money Not nearly as rich as her but I make low six figs
your social status Bach Degree in Math/CS, full time corporate job last 6 years
your personality obv i'm fine here so far, she's coming back for more
your looks okay so i'm very avg looking, but im tall and in decent shape

so it sounds like you better do a lot of work on personality.

[/ QUOTE ]

love how you jumped to this conclusion though. my point is not that i'm some loser, just that i am seemingly out this woman's league and looking for ways to close the gap.

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
OP,

If you have any thoughts about Powerball numbers this week, please send a PM.

[/ QUOTE ]

No idea what this is supposed to mean, curious though.

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
[ QUOTE ]
women are interested in:

money Not nearly as rich as her but I make low six figs
your social status Bach Degree in Math/CS, full time corporate job last 6 years
your personality obv i'm fine here so far, she's coming back for more
your looks okay so i'm very avg looking, but im tall and in decent shape

so it sounds like you better do a lot of work on personality.

[/ QUOTE ]

love how you jumped to this conclusion though. my point is not that i'm some loser, just that i am seemingly out this woman's league and looking for ways to close the gap.

[/ QUOTE ]
Well, whatever happens make sure you bring some Simon and Garfunkel CDs to set the mood.

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
lebow,
dude you are soooooooooooooo wrong about older women liking younger guys...
damn, your list is of what younger women want in a man. Established women want good company and great sex. older men seem to suck at both of these.

[/ QUOTE ]
really, in movies they always say that older guys are better in bed than young guys. maybe that justs kevin coster, sean connery and harrison ford?

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
[ QUOTE ]
OP,

If you have any thoughts about Powerball numbers this week, please send a PM.

[/ QUOTE ]

No idea what this is supposed to mean, curious though.

[/ QUOTE ]

I think he's saying you're lucky as hell.

Re: Impressing (Hot) Older Women
 

op,
you better make sure she isn't on this nsfw website before you become romantically involved.

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
Let us know how badly you feck it up.

[/ QUOTE ]

Hooha!

Re: Impressing (Hot) Older Women
 

[ QUOTE ]

really, in movies they always say that older guys are better in bed than young guys.

[/ QUOTE ]
I think she's looking for quantity over quality here.

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
Well, whatever happens make sure you bring some Pat Benatar CDs to set the mood.

[/ QUOTE ]

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
op,
you better make sure she isn't on this nsfw website before you become romantically involved.

[/ QUOTE ]

actually a possibility considering where i live...

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
[ QUOTE ]

really, in movies they always say that older guys are better in bed than young guys.

[/ QUOTE ]
I think she's looking for quantity over quality here.

[/ QUOTE ]

god i hope so.

Re: Impressing (Hot) Older Women
 

[ QUOTE ]
[ QUOTE ]
[ QUOTE ]
women are interested in:

money Not nearly as rich as her but I make low six figs
your social status Bach Degree in Math/CS, full time corporate job last 6 years
your personality obv i'm fine here so far, she's coming back for more
your looks okay so i'm very avg looking, but im tall and in decent shape

so it sounds like you better do a lot of work on personality.

[/ QUOTE ]

love how you jumped to this conclusion though. my point is not that i'm some loser, just that i am seemingly out this woman's league and looking for ways to close the gap.

[/ QUOTE ]
Well, whatever happens make sure you bring some Simon and Garfunkel CDs to set the mood.

[/ QUOTE ]

haha good advice IMO.

Re: Impressing (Hot) Older Women
 

[ QUOTE ]

I don't normally grammar-police, except you did it twice in the exact same context.

[/ QUOTE ]

Jackass

Re: Impressing (Hot) Older Women
 

Tell me more about the 19yo with the rich mom.

This should be your obvious play if the daughter is nearly as good looking as you say the mom is.