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Dating A Younger Woman


New Member
Mar 17, 2011
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Hey guys, I'm new here, so let me give you a little background. Over a year ago I got out of a LTR (9 years) we had a house, cars etc. Glad it's over no regrets at all, she wasn't the one. Have an awesome place now and loving life again.

During the past 12 months or so I've been doing fairly well with the ladies (14 at last count in that time span). I'm 31 and most of the women were within 3-4 years either side of my age, I have found it easy to engage them because we have both had similar life experiences.

Here's the current Situation:

I have a date tomorrow with an 7.5/10, 21 year old woman. We have 'met ' via an online dating site and talked on the phone. She's in school, works two jobs and lives with roommates. Seeing as this is the first time dating someone much younger than me, I'm looking for advice. To date, she has already sent me two pictures of her wearing lingerie and I didn't really ask for them. My question to her was, "do you have any pictures you can send to me".

What do you guys think?


Master Don Juan
Feb 18, 2010
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Standing At The Crossroads
If she sent you unsolicted lingerie pictures, it tells me that she places a high value on her coochie. Likely an AW. I don't see a problem with the age thing. Roll with it.

This one seems like a done deal.

Edit....if she sent you those pics, you can bet your azz she's sent them to other guys.


Master Don Juan
Feb 19, 2009
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Be prepared for the obvious: someone who is needier, less mature, and has less direction in life.

Other than that, if you're willing to pay, you have the right to play.


Master Don Juan
May 5, 2010
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Dude, you're just going out. It's not like you're gonna marry the chick in two weeks. Relax and have fun.

The pics, yeah, yellow flag. Keep in mind that she's young and most of the guys she's known up until now don't really place much value on her character as their primary concern is her "hotness." Therefore she puts forward what she thinks her "best card" is: her body. Go with it. Don't mention the pics. If she asks, tell her "You look great sweetheart" or something like that but don't make a big deal out of it.

I am currently dating a 20 year-old. I'm 36. We have an interesting dynamic. Read Rollo's post in the thread. Incorporate this into your interactions with young women.

As for me, IDK how long this is gonna last but in the meantime, I'm enjoying it and I'm kinda molding her to my liking. Something that is really hard to do with an older woman who is already set in her ways... ;)

Edit: I forgot to address the "do you have any pictures you can send to me" request. I'm gonna share my slightly C&F line for when girls ask me for pics: "No can do sweetheart. My agent has expressly prohibited me from distributing my likeness without the appropriate financial compensation. We don't wanna get her mad now do we? ;)"


Jan 31, 2005
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From New Orleans, Louisiana to Atlanta, Georgia!!!
I can't f**k with younger women. I just can't do it. I'll date a woman twice my age anytime!


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