I'm considering whether or not I should do it because she lives in my townhouse complex so there's always a chance I would run into her if I say the wrong thing. But I also just want to get it over with because I see her tanning at the pool all the time and it's so crazy.
Your making your post sound as if the question was "have you ever f*cked a MILF". What's the problem with talking to her? Do you only talk to women you want to get laid with? Are you sure you really want her, just because she's making you fantasize, when you don't even actually know each other yet?
Fuck milfs, and fuck their actions. Dont fall to their dirty games. Dont talk to her, ignore them you are better than that
The problem is that you are thinking of her only as the person you want to do this one thing with. If you considered a human being just like everyone else, there wouldn't be that much of a problem. Did it ever occur to you that this might be because of all the porn you watched?
I waited and I'm still waiting...don't wait. I've had to decide that I need to change my approach. Take my advice and pursue the ladies. They don't come to you bro trust me.
Well this girl actually agreed to hookup with me, we made out on her bed a few nights ago. I just don't know what I should say to the MILF.
Like I said firstly unless you are 18+ don't bother. She doesn't want an underage person hitting on her. If you are 18+ though, I dunno, if you know her name or surname, compliment her when you walk past her and give a cheeky smile. She'll either be like wtf, or it will make her day that a young guy is complimenting her.
If you are interested in starting a relationship with this women, OP, I suggest you stop calling her a MILF.
Dude, this chick is a easy mark. All you gotta do is get a fishing pole and swing it her way when she's tanning by the pool. When she notices and says "Hey! WTF" just say, "Oh, I was just fishing for oysters and I thought you were a pearl, what's your name?" and then she'll tell you her name, "My name is Milf or whatever" and then you just say, "Well, Ima call you Pearl , my name is Christopher123 by the way". Wam! Bam! Done. Don't forget to write me a check. You ask a lot questions about older women by the way, don't ever get in to a relationship with one. Getting women is kind of like fishing, all you need is a good boat and some bait, just remember that not every fish is gonna bite and some fish are poisonous. Just ask Jordan Belfort. Cheers mate.
Dude you're on fire, I'd say go for it. It's all about confidence and you seem to have it in swagger loads at the minute. Is she good looking? Which do you prefer the milf or the girl you're about to fuck?