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Old 11-06-2011, 07:58 AM
 
Location: Cornelius, NC
1,045 posts, read 2,657,362 times
Reputation: 679

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I'm a 26 year old single guy and just looking to meet an attractive older woman to date. I went to this place called the Lounge last night and figured I might have a shot at finding someone there. Any success stories from other young guys on here? Where did you go and what did you do? When is the best time to go to these places? Saturday night seems too crowded. Everyone is just with their friends and no one seems like they are looking to actually meet anyone.
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Old 11-06-2011, 08:23 AM
 
28,455 posts, read 85,339,930 times
Reputation: 18728
Thursdays tend to be a little less of a "friends night out" then the weekend when more people schedule who they go out with...

If you believe me the "pickup artist" type stuff it probably pays off to be the flashiest dressier in a nightspot, and if you go to a place where the opportunity to dance in a more suggestive manner is OK that too probably will increase your odds of finding someone looking for a more physical relationship.

Thing is, I sorta question how much of the "attractive older woman looking to hook up with younger guy" thing is a myth / applicable to such a small portion of the population as you are more likely to find a unicorn.

Think about it -- yes, Ashton and Demi seem to have been together for awhile now (who know how much longer they will be...) but it is not exactly like she needed "spousal support" from Bruce Willis on her earnings, and if Bruce does a decent movie once every five years or so that is more than enough to keep up the payments for the kids. Normal divorces are not like that. Even stunningly attractive woman with kids in the Chicago region cannot afford to do anything to jeopardize their spousal support with the high cost of living and relative lack of employment flexibility. If an older woman is single or divorced without kids what are the odds of them having ties to a region with rather inhospitable winters, housing costs that are in the upper reaches nationally, limited potential for "glamour" type employment and an unbalanced set of taxes / disincentives to entrepreneurs...

Maybe "cougars" are more prevalent here than other rust belt communities, but for the reasons I've laid out I doubt anyone would claim there are attractive older woman looking for younger guys in anywhere the numbers that match the coasts...
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Old 11-06-2011, 08:31 AM
 
Location: Cornelius, NC
1,045 posts, read 2,657,362 times
Reputation: 679
Well I make decent money for a 26 year old bloke and I will dress very flashy and show my wealth. I'm just looking to date a cougar. I would prefer that she is not tied to anyone else as I don't want to deal with that ****. I don't care how much money she makes and as long as she is at least a 7 on the looks scale and can have a decent conversation with her, then we're good to go. So what are my chances here in Chicago of finding this? I can see how Thursday would be a good time to go. I'm definitely never going on a Saturday night again. Too many damn people and can't have a conversation because it's too loud. I'm not looking for that.
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Old 11-06-2011, 08:36 AM
 
2,115 posts, read 5,416,337 times
Reputation: 1138
Your best bet is to hang out around some of the spots in the Gold Coast and maybe River North. Dress to impress like chet pointed out and get ready to probably spend some money as well.

Quote:
Originally Posted by Caldus View Post
I'm a 26 year old single guy and just looking to meet an attractive older woman to date. I went to this place called the Lounge last night and figured I might have a shot at finding someone there. Any success stories from other young guys on here? Where did you go and what did you do? When is the best time to go to these places? Saturday night seems too crowded. Everyone is just with their friends and no one seems like they are looking to actually meet anyone.
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Old 11-06-2011, 08:49 AM
 
Location: West Paris
10,261 posts, read 12,507,136 times
Reputation: 24470
Quote:
Originally Posted by Caldus View Post
I'm a 26 year old single guy and just looking to meet an attractive older woman to date. I went to this place called the Lounge last night and figured I might have a shot at finding someone there. Any success stories from other young guys on here? Where did you go and what did you do? When is the best time to go to these places? Saturday night seems too crowded. Everyone is just with their friends and no one seems like they are looking to actually meet anyone.


on websites
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Old 11-06-2011, 08:52 AM
 
Location: Cornelius, NC
1,045 posts, read 2,657,362 times
Reputation: 679
Quote:
Originally Posted by french paris View Post
on websites
Haha I'm done with websites. Too much bull****ting on there too. :P
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Old 11-06-2011, 08:55 AM
 
Location: Cornelius, NC
1,045 posts, read 2,657,362 times
Reputation: 679
Quote:
Originally Posted by reppin_the_847 View Post
Your best bet is to hang out around some of the spots in the Gold Coast and maybe River North. Dress to impress like chet pointed out and get ready to probably spend some money as well.
Yeah that's what I did last night. I dressed up real nice and looked rich. But I think I just need to do it on like a Thursday night or something. I asked out a ton of women but got nothing but I think a lot of women that go out on a Saturday night are just looking to hang out and have fun and nothing else. Probably already have their boyfriend or just not looking.
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Old 11-06-2011, 10:07 AM
 
Location: West Paris
10,261 posts, read 12,507,136 times
Reputation: 24470
Quote:
Originally Posted by lorielicious View Post
Let me google that for you (http://tinyurl.com/chvk24a - broken link)

lol
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Old 11-06-2011, 12:00 PM
 
Location: Los Angeles
928 posts, read 1,712,672 times
Reputation: 1298
Heh. No, no, I kid Caldus. He knows I think he's terrific.
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Old 11-06-2011, 01:40 PM
 
2,115 posts, read 5,416,337 times
Reputation: 1138
I think you will yield better results on random nights and maybe even daytime hours. Gotta remember, Saturday night is prime time and a lotta these folks are out either trying to see & be seen or they are out drinking and having fun as you stated. Additionally, they might be out with a whole crew of friends or their man, and their shield will be way up due to the # of creeps that go into hyperactive mode on a Friday or Saturday night. This is prime time for those folks as well, lol.

I honestly think that your approach will only get you a very flakey, artificial lady (if it even works out) to hook up with at best, but if all you're after is a fling then go for it.

Quote:
Originally Posted by Caldus View Post
Yeah that's what I did last night. I dressed up real nice and looked rich. But I think I just need to do it on like a Thursday night or something. I asked out a ton of women but got nothing but I think a lot of women that go out on a Saturday night are just looking to hang out and have fun and nothing else. Probably already have their boyfriend or just not looking.
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