How to handle a MILF?
Went to a bar last weekend and there was a pretty fine MILF Bartender. This was shortly before closing, as she was putting everything away I came up to her and this is how our conversation went.

I was drunk at the time and this was a few days ago so it’s not that accurate, but this is the jist of it. She had a smile on her face the entire and the entire conversation was playful.

“I need a refill on my water please.”
Once she brought refilled it I followed up with “…and your number as well.”
She laughed and said “You’re a kid to me. I have a 27 year old daughter.”
“That’s fine with me.”
“It’s not fine with me. How old are you anyway?”
“How old do I look?”
“I don’t know, 28-29?” (I’m 22 and she carded me about 15 minutes prior, there were only about 5 other people in the bar so I don’t know how likely it is that she forgot my age.)
There was another minute or two of me trying to talk her into giving me her number. I ran out of things to say and after a few seconds of silence and somewhat intimate eye contact she just walked away and continued cleaning.

I really wanted to use the “old enough to know how and young enough to go all night” reply to the age question, but saying it to a hired gun definitely seemed like an inappropriate dickhead thing to say in my mind.

How should I handle a 2nd attempt? What could I improved on in the 1st attempt?

Thanks!

Hot bartenders hear lame lines from douchey drunk guys all night long. Nothing about what you said suggested that you are any different, and you can bet she was thinking the same thing.

Your boy,
870

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I don't disagree, but how do you recommend I proceed?

i say take a risk and do something rediculous that noone has thought of

give her a nickname and neg the shit out of her she a hired gun she probally heard evry line in the book but shes a older peorson so you need to talk to her about relevent stuff

This kinda thing has worked for me rather well a couple of times (when I assumed I deal with a woman that heard it all):
Best delievered with a cocky smile of course

"I bet you heard all the worst pickup-lines allready, but I assure you I can do worse!"

You have a very good chance to get blown out here, I sure was lol BUT more often I got a big grin and something like "Really? Let´s hear it". I usually say "Bet I can drink more then you can!" but you should say something really silly that suits you. The idea is to make her laugh, cause as Catherine Deneuve said "A woman that laughs is a conquered woman"

Playfulness is key, and Dude BE SOBER!!!

You need to appeal to her natural sexual drive. Show maturity in your demeanor but confidence in your desire. Straight and to the point would work best here. You are obviously not dating potential, with that being said, you need to appeal to her sexuality.

A straight forward comment is your only shot here. Be mature and keep a straight face. say something like this: ( while looking her straight in the eye, and take talk to her away from anyone else)

"Listen I know I am not your ideal suitor, as I am much younger, but I find you overwhelmingly attractive, I don't normally pursue mature women, but I find my self completely drawn to you. I feel a strong sexual urge towards you. I am not looking to fall in love or anything like that. If you would at least humor me and meet me for a coffee, I would love to show you that I am a worthy of your time.

I promise anything from this point on between you and I will be completely discreet. Life is too short not to follow overwhelming urges. Here is my number, I'll let you think about it. Get back to me regardless. I will respect your decision either way"

( have your number already written down, keep the conversation extremely private and quick, do not show any more attention to her at her place of work once you have dropped your digits on her, she must know you are serious about keeping it discreet)

_________________
Seduce their mind and the rest will follow.

Not bad Sex Addict, but how is the boy supposed to keep it quick and discreet when he´s supposed to give her such a long speech? Not saying it wont work though. It really doesn´t matter what he says actually, as long as he delivers it with unshakeable confidence. I agree with that part. And again:BE SOBER!!! The last thing a grown woman wants is a drunk kid! Especially if she´s a bartender!

How long did it take you to read the "speech"? I'd say a couple minutes is pretty quick. What I meant by that is once you are done saying what you have to say, that you leave it at that and eject.

Of course it matters what he says. She is obviously not interested in any type of dating situation or having a 22 yr old kid pine-ing over her after she sleeps with him. Especially if he may go to her work in the future and fuck with her lively hood, so the only real chance he has is to lay the cards on the table and re-assure her its purely sexual, and will be 100% discreet. Without re-assuring her of these things prior, he will not have a snow balls chance in hell of her even considering it.

I'd also consider reminding her that you will no longer come into her place of work if she agrees to an encounter.

By eliminating as many possible reasons for her to say no as possible with your initial invite, you will give yourself better odds to seal the deal.

And yes, Be COLD SOBER. If you can walk in drop your invite then leave, you will have a much better chance. Or drop the invite, stick around for one drink then eject. The more secretive you can make it all, the better.

_________________
Seduce their mind and the rest will follow.

Wow.Yeah when it comes to gaming milfs I found that negging them really does the trick.I try to make them feel insecure about how old they are.

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Don´t get me wrong, Sex Addict, I think you are giving great advice here, and I give you that you are most likely to be my senior as far as gaming is concerned. I still believe that keeping it (much) shorter is still not wrong. She´s a bartender and she´s at work. She´s not likely to have the time to listen for too long. I worked in bars often enough to know that it´s generally a stressful job and that being held up can often be annoying. But if it´s a quiet night...
If she has a 27 year old daughter then she can easily be 50+ which means she´s is even older then I am (lol), and I know how hard it is for a very young person to impress someone that mature. The more collected our friend appears the better, that´s why I believe that Psychotic should try to get the essence of what you suggested across in less words, even on a quiet night.
I don´t know how old you are and if you have kids yourself, but I assure you that getting her to see him as a sexy young man as opposed to a "cute kid" is VERY hard.
But worth a shot cause he might be in for the ride of a lifetime

This is really going to be interesting and I can´t wait to hear how it went. I liked mature women when I was that age and still do, so I´m totally rooting for you Psychotic!

Since she's said that she's so much older than you, just neg her for being old.

Nickname her "Grandma" or "Nanna" for a laugh. Ask her why she still works in a bar at her age. "Looks like someone's pension didn't come through this week."

For the record, the above is not negging. This is playful, teasing banter. It's fun, lighthearted, and because you'll say it with a shit-eating grin and appropriate inflection, there's no possible way anyone could take it seriously.

A neg is not the same as banter. It is an insult meant to look unintentional because it's dressed up as a compliment, and it's supposed to be targeted directly at something you think the person might be insecure about. This isn't fun, it's not lighthearted, and there's a good chance you will actually hurt somebody's feelings or at the very least make the interaction less fun by doing so.

This is an important distinction a lot of new people seem to miss.

Your boy,
870

_________________
"Do not blame, call out, alpha male, superman, or water sprinkle any hoes. And what will be, will be." -Hobbit

http://tinyurl.com/c6lbje<-Member Journal (PMZ Only)

870 just pointed out something very important! Calling a woman that is 40+ a grandma is not negging. Making any kind of similar remark to a mature woman is not charming and not playful, it´s simply cruel and tasteless and I doubt it will give any desirable result. Bear in mind how important youth and beauty are to women in general, important to a degree that we men will never understand. They want to be desirable and their self-esteem revolves around this so much more then for men. We get cooler, more masculine and interesting with age. Women just loose something that defines them as sexual beings and that is a slow and painful process. Trying to "neg" on this basis is simply mean and insulting.

Thanks for clarifying that. Please excuse my ignorance.