Older Women Reveal The Worst Ways Guys Have Tried To Chat Them Up

How NOT to flirt with a 'MILF'

American Pie star Jennifer Coolidge.
Jennifer Coolidge The original MILF in American Pie 3 Image Universal

Everyone has a type: be it blonde, brunette, skinny, curvy… However, some guys are specifically more attracted to older women than people their own age.

In fact, it was recently revealed that ‘MILFs’ are more popular than ever on adult movie sites…

It’s not just adult movies where this trend is evident either; plenty of younger guys have tried their best to charm older women, and – invariably – failed miserably.

Now, a group of older women have taken to reddit to share their horror stories about being approached in cringe-worthy ways by younger men.

See some of the stranger stories below…

The Gradate
The Gradate The classic Dustin Hoffman movie


The Teacher

“Every moderately attractive high school teacher has been hit on. Currently, a senior that graduated last year is patiently waiting to turn 21 so he and I can go have a beer. I’m sure in his mind this will lead to a weekend of wild sex where I show him the hidden secrets of the Kama Sutra. I’m just interested to see if anything will have changed by then. Also, one of my son’s friends once told me he’d “like to experience an older woman” and then stared at me.” – anothermochaplz


The Fighter

“I wouldn’t say I’m a MILF, but 2 of my daughter’s friends have hit on me and her boyfriend of 3 years tried to kiss me. The most desperate was the boyfriend. We had gone on vacation for my daughter’s 21st birthday to a small town with hot springs. While my daughter, her boyfriend and her friends camped nearby, I chose to stay in a hotel to give the young people their privacy. We all went together for a soak one evening but my daughter wasn’t feeling well and stayed at the Campground. After the soak, the boyfriend was quite drunk so I gave him a ride back to the campsite. When we arrived, he started professing his undying love for me, said my name 3 times in his most serious attempt at a sexy voice and leaned in for a kiss. He never saw my fist, but felt it land squarely in his sternum. It made for an awkward morning. He confessed to my daughter the next day and she laughed hysterically at his ridiculousness. They broke up not long after.” – inconditenarrative


The “Bitch”

“I have two teenage daughters and have had several of their guy friends hit on me. We moved to a new town a few years ago and both my girls are quite pretty so they had a lot of new guy friends that would come over and hang out. I would talk with them in the group and kinda hang around and listen to what was going on. Some of the ones who looked older would say things just to see if they could get away with it. I can’t recall most of the things that were said but two stand out to me. The first one happened when my daughter came in with a group of friends and asked me to give several a ride home. I told her I just needed to hurry and change out of my gym clothes and I’d be right down. Next thing I know there’s a knock at my bedroom door and I ask who it is (my daughter wouldn’t knock) From the other side of the door I hear a boy ask if I needed any help changing. I told him to get his ass out of my house. The second one happened at a party we my other daughter threw at our house. One of the boys came up and put his arm around me and asked to see my tits. I was so shocked I couldn’t think of anything to say other than fuck off. Then I told him to leave. The next day he called my daughter and asked her to ask me if he would ever have a chance. Seriously?!?! It finally got to the point that she asked me not to come around when her guy friends were over and not to talk to them when I see them at the school because she was sick of hearing things about me from the guys. I had to start just being a bitch after that because obviously me being nice was taken as something other than what I’d intended and I didn’t want to embarrass my daughters any more.” – SuperHighSkiBunny


The “Exotic” One

“I don’t consider myself to be a MILF, but I have had my sons’ friends try and make moves on me before. I am younger (had my first kid in my early twenties) and am “exotic” (Colombian immigrant in a small southern town). I think those play more of a role than my actual looks. Just something different than what the teen boys here are used to. The weirdest one was when my boys had a couple of friends over to watch a movie a couple of years ago. I believe they were 14 and 12 at the time. I was watching the movie with them and one of the boys (14 years old) put his arm around me. I didn’t want to make a big deal about it and embarrass him or anything, so I tried to subtly get out of the situation. I yawned and I told the group that I was going up to bed and he stood up and started following me. I asked what he was doing and he said he thought I wanted him to come up to bed with me. I explained that I was sorry for the confusion, but that I absolutely did not want him to come up to bed with me. He apologized and returned back to the media room to watch the movie with the rest of the boys. My oldest is a senior in high school now and has been asked by his friends if they can take me to prom if they can’t find another date.” – Colombiana

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