How do you approach mature women?

I'm a guy in my late 20's. I've recently realized I'm very attracted to older women, late 30s onwards. They're the kind of women I find intellectually most stimulating, and sexually more attractive (when I watch porn, it's usually about younger guys with older women).
Thing is, I don't know the first thing about approaching a mature woman with dating or sex in mind. In my context it's mostly been friends of my parents, superiors at work, teachers and such. All my partners so far have been girls my age or younger. Only once did I try to talk to a woman in her 40s at a coffee shop, and she was kind of condescending. Kind of like a mother talking to a lost kid.
Anybody with this kind of experience, or any advice?


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  • Be direct and flirt with her. Tell her how great she looks. A little sugar will go a long way. The great thing about older woman is that they know what you want and know what you are doing. If you are lucky to get one in bed, she will give you the best sex of your young life, trust me .

  • I'm 24 and I've tried this route and just want to say "beware." In the last couple of years I dated two divorced women for a period, one was 37 and the other was 42. The one who was 37 was great in the sack, but had been married twice, had kids 10 and 5, and I shortly learned why she was divorced twice: she was a headcase. Really bizarre flying off the wall type of mind and insecure too, because she had been dumped a few times in her life. The one who was 42 lasted a little longer, we dated for 9 months, but she too had kids aged 16 and 13 and though the sex was awesome I felt like I was behind her kids when it came to getting attention and shit. She just liked that I helped with the bills.

    Most older, single women have significant issues or baggage, so be prepared for that. I'm not sure if a piece of pussy is worth it, no matter how good it feels. I'm back to dating people in my age range and couldn't be happier.

  • When I was about 24 I saw an older woman walking down the street. She was wearing a short mini-skirt and some sexy high heels and a wig. I decided to try and hit on her just to see what she was into. It turns out she was whoring. But she made it clear she didn't mess around with young guys. So she turned me away. But her big ass looked good as hell in that mini and it was gonna take more then a simple "no" to make me go away. So I hit on her again. I assured her I was older then I looked and that I would pay her whatever she wanted. So she agreed and we went to a motel. That's when I found out she was in her 60's and she loved to fuck. Well we had amazing sex. When that old pro got through with me I was trying to get her phone number. But she told me she had a pimp and she couldn't give it out. But that 60 year old pussy was amazing. If she didn't have a pimp I would've made her my woman.

  • Go to a casino and have a few drinks but make sure you are not driving.

  • Approach them with confidence and forthrightly ask them, " M'am, is it true that men are as old as they feel, but, women are as old as they look ? " Drives them WILD !

  • It should be the other way round.That excites them.

  • Best way to approach mature women I have found, is to go down to the local retirement home or assisted living facility. Most old women there are delighted at the prospect of having their old cooch dusted off and brought out of retirement for an hour or two. Those Depends undergarments are hella sexy too.

  • You poke fun, but the reality of it is there are many women 30, 40, even 50 year old women who are hot as fuck. These women know what they want, and sex is way better than with some flighty teenager or even 20 year old. So while you are doing all the work for mediocre sex with some 19 year old no nothing. I'll be getting rode like a bull from some 40 year old who knows how to fuck me silly.

  • Amen brother. Best sex I ever had was with my best friends mother. I was 19 when a storm hit our area and tore up a bunch of shit. My buddy was at work when the storm hit. He called to see if I could go help his mom who had just divorced his dad because he ran of with some young thing. So I go over and she is pretty shaken up, but there is no damage to her place. So I'm sitting there trying to comfort her the best I can, and she's crying about the storm and everything that's going wrong in her life. Now I have no fucking idea what to say to her, so I'm just sitting there listening and nodding my head, thinking I'm going to fucking kill my buddy, right. About then she leans in and gives me a kiss. Next thing I know she fucking straddling my lap sticking her tongue down my throat. Now she's 38 years old and not bad looking, I just never thought of her in a sexual way, so it kind of took me by surprise. So I push her off of me. She instantly starts crying hard saying she's going to die an old woman alone with no man. So now I feel bad and try to comfort her again telling her she beautiful and that I didn't expect her to kiss me, and so on. Basically kissing her ass. So she fucking jumps back on my lap and starts fucking kissing me again. Only this time I fucking kiss her back and she's ripping my clothes off. This woman fucked me like I never been fucked before. She did things to me that I thought only porn starts did. I'm pretty sure this woman was the best sex I will ever have.

  • First, like others have said below, you better have your shit together. Good job, your own place, and future plans. The last thing a MILF wants is another child to take care off, so have your shit together and be confident first.

    Next, it's harder to find single 40 year old women after they have spent 20 years in the game already. Most of them are already married, so you need to be open and look for women who are divorced. Start paying attention to the dissolution of marriages in the local paper. It's like the perfect list of available MILF.

    And last, if you are looking for a relationship, you better be open to raising some other mans kids. The most important thing to remember is her children are her number one priority. You get the MILF by getting the kids. If her kids love you than she will be more attracted to you. So pay attention to her kids, but be careful to not pay too much attention because that's just creepy and she may think you're either not mature or after something else.

    I hope you find a good MILF, they are the best. I have been married to my MILF who is 14 years older than me for 19 years now and I wouldn't change a thing. Good luck

  • Four words: have your shit together. If you have a good job, are making money, and are willing to spend it, you will attract a lot of MILFs on the rebound. They want security, and they will give up pussy for it.

    They don't want another child (they likely have those) or someone they need to support. You have to bring a good "game" to them.

  • You pretty much treat us just like younger women but one thing to keep in mind is older women usually know the routine. We can spot a dog from a mile a way so if we are not into casual sex, younger guys or what ever we spot that turns us off your not going to get anywhere.
    You just have not met the right older woman yet.

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