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Category: Dating

How Not to Screw Up When Dating Single Milfs

I remember the first time I chatted with a single milf, and it was several years ago, I think it was over 15 years ago, I was in an MIRC chatroom. If you haven’t heard of MIRC, you’re lucky because that means you’re young. MIRC is basically older than Yahoo Chat, and older than AOL Chat. I know that sounds ridiculously old, but it is. The funny thing about MIRC is that it’s still alive. It’s still going on.

Anyway, I was hanging out in the room and was talking to this chick from Illinois who said she had 3 kids, and she said that she was a single mom. So far so good. It seems like she was very comfortable, and I was cracking jokes, and I was comfortable. Things were going quite smoothly.

I was basically ready to ask her for her phone number or maybe some nude pictures to get the ball rolling, but then I fucked up and asked the question. What the fuck did I say? Well, I asked if the fathers of her kids were different. In other words, if she had sex with 3 different men to produce 3 different babies.

As you can probably already tell, that line of questioning did not go over well. In fact, it went over well like a lead balloon. In other words, I crashed and burned. The funny thing about all of this is that it was one of my first lessons in screwing up when trying to date single milfs.

You have to understand that a lot of single women who have kids are facing many different issues. It’s really fucked up if you think about it because if you step into their shoes, it’s rough. It’s rough being a single mom and you can’t just base your conversation on your need to have sex with her. It’s just not going to work.

You have to communicate on a very real basis. In other words, be curious about going on and really try to know her. While both of you know that, ultimately, it’s all about banging and having anonymous sex, a little bit of humanity goes a long way.

You have to understand that it’s too easy to screw up dating single milfs @ because they can be very touchy and I really can’t blame them. So be aware of the questions you ask and be aware of the assumptions you bring because they can fuck you up in a big way.