Tips to Successfully Dating Middle-Aged Women

Having been newly divorced this at age 45 and re-entered the dating scene for 5 minutes, I found that men at this stage in life appear to…

Tips to Successfully Dating Middle-Aged Women
Mature African American Man

Having been newly divorced this at age 45 and re-entered the dating scene for 5 minutes, I found that men at this stage in life appear to be as clueless as they were in their 20’s in how to communicate, attract and date a woman. I realize that dating at this phase of life is difficult for may reasons (finances, illness, scars from previous relationships), but fellas you need to know mature women just don’t have time for your shenanigans. You only get one chance to make that good first impression with us, and we lose interest in a matter of seconds.

After being approached (and irritated) by men this year, I thought I’d write a list of tips of things that mature, middle-aged women would appreciate me sharing of things we expect and like (and the shit we definitely we do not), which should be common sense.


Please Put The Phone Down!

Men, we want your undivided attention, especially when you’re hitting on us for the first time. Please don’t try to get our attention while taking calls, and making calls. It’s rude. It shows you are distracted, and your attention is all over the place. If I am worth your time and attention, please give me yours! It’s common courtesy and tells us we matter for the brief moment. Also, if you happen to get to second or third base with us, PUT THE FUCKIN PHONE AWAY!

We don’t wanna hear your alarms, chirps, and beeps all night when you’re on our time. If you are making business calls in my bedroom before or during my nookie time, it will only happen once. I can promise you THAT! Still diggin in your child’s mother’s pussy on occasion, and she calls on the regular or you got some other stuff going on with your ex……I am not stupid. Fix that before pursuing a new relationship. It will ruin it every time. So save the drama for the young needy girls with low-self esteem. I got the T-shirt for that bullshit.

Multitask on your time, not mines. Especially in the beginning of the relationship. Don’t attempt to make that my norm in the new relationship. I am not having it.


Video Games…..Nooooooooooooooooo

Grown Men Playing Video Games

If you think that you are going to talk me to death about video games at 45–50, you’re dead ass wrong! I got enough going on in real life just trying to make another day. Working, caring for a home, seeing my grand kids and traveling. I don’t want to hear about your fantasy world of video games with people all over the world you play online every single day. I especially don’t want to hear about it if it prevents you from doing things like caring for your kids, getting a job and being gainfully employed, or if have a conversation about current events. You immediately start to look unattractive to a strong, confident, independent woman not willing to sacrifice or settle.

If a good day for you is going to Game Stop and getting the latest version of video game………then the mature middle-aged single woman really isn’t interested in you. Don’t stop, keep walking and get your life up so you can have something to talk about with her that she can relate to.


Brush Your Teeth & Tongue

Pretty self explanatory. Please brush and floss. There is nothing worse than looking into the face of a man attempting to hit on you, and he doesn’t take care of his teeth. He has plaque in between this teeth when he smiles, and his tongue is yellow. And breathe, oh for heavens sake please make sure your breath is on point before approaching middle-aged women. Good hygiene is everything to us. Don’t slack on taking care of your teeth. Your first conversation depends on it! If you’ve consumed a great deal of alcohol, you may want to gargle or wait on another time. Alcohol and bad breath are just not a good combo!


The Well-Dressed Man Gets the Second Look


Fine Clothing Still Matters

You don’t need to have a lot of money to look nice. You can even buy nice things from thrift shops. Looking like a decent middle aged man is so attractive. I realize society is a constant state of relaxation and workout look mode, but clothes still make the man. Unless I am at a place where it’s constant vacation mode (like FL), or ball game or near a gym, I don’t expect to see the middle aged man with athletic gear on all day long. Now, if I see you and you look as if you just ran out to pick up something, but you look nice and tidy that’s different. That look is kind of sexy actually.

Now, if you are a guy and your entire wardrobe consists entirely of name branded warm up pants, t-shirts, hoodies, basketball shorts, and those velcro flip-flop shower shoes that open at the toe, my heart is sinking. No matter how cute you are, the middle aged woman is not necessarily into the name brand athletic sportswear head. You don’t have to have a 3-piece suit every time we meet, but have a diverse wardrobe that indicates you know how to dress for various occasions. That says to us you likely know how to communicate well, which is my next topic.


Communication is Essential

Man and woman engaged in a nice, non-threatening conversation

Good communication is essential to getting anywhere with middle-aged women. Verbal and non-verbal cues we pick up on quite quickly. We are super perceptive, and we can see through your bullshit. We can tell from the way you engage us initially whether you’re looking for something long-term, or if you simply like the way we look and you simply see us as your temporary bed wench. Tell the truth, and be yourself. We recognize fake stuff.

I personally hate talking to a guy, and the first time he meets me the first question that comes out of his mouth is can he come to my place for dinner or to visit. Why would I allow you into my home? I don’t even know you. Am I supposed to buy food cook, clean my home to entertain you? Are you going to try to force yourself upon me as soon as you enter?

Men, if you don’t have any better sense than this at this stage of life, you don’t even deserve a date!

No woman putting her safety first is going to allow you into her, so stop propositioning it. You may as well just say I wanna fuck you but I just gotta find a way to make it sound like I don’t. We can read between the lines.

If you don’t have the resources to wine and dine me, take me to a nice coffee shop so we can talk. It’s clean. It’s safe. And it’s an inexpensive neutral date site that won’t make you the guy feel like you are paying for a day that may or may not have any potential. I am interested in your mind, not your money per se. I also want to know you’re not auditioning for the help! No suggestions about my place. Allow us to invite you. If we never invite you, we don’t feel like it’s time (although some women may just be bad housekeepers or not live alone).

The bottom line is that it is absolutely a turn off and we understand what you are subliminally attempting to convey, and we aren’t interested!

Speak your mind, no tricks no games. Skip the hidden agendas. We haven’t lived to get this old without learning a thing or two about men.

And please don’t ask me about sex. Don’t ask me anything about it. If you do, even if there is chemistry, we are shutting down. Men, your reputations precedes you, so we are always afraid you’re taking us for a ride. Let things happen organically. Also, don’t talk about your kids too much, neither your ex. We don’t want to hear too much about your job either, unless it’s interesting and we inquire about it. Men tend to associate who they are with their work, which is not the same thing. Learn about who you are, and learn how to talk to us about it.


Don’t Offer What You Can’t Afford/Unwilling to Pay For

Woman eating alone

I eat alone alot. I like eating alone. Depending on where I am, I often get offers for company by men which is cool. I always turn them down because I love my alone time. But more and more often, a guy will see me and a girl friend out without a guy and they will come over to offer me a date. A dutch date. I am 3 seconds for getting into his ass about how stupid it is for him to make such an offer, but rather than cause a scene I simply say “No thank you.” Then he commences to ask me all these leading open-ended questions which borderlined insinuations of I was an angry, bitter woman and I didn’t like me.

Oh no sir, you’re wrong. I love men. I just hate stupid ones. And I hate cheap ones. With your first time approach, and offer to take yourself to lunch illustrated many things to me. Money is tight for you, or it is at least a concern. Maybe you’re a serial dater, so that’s your way of counting beans. Maybe you have to pay child support and alimony. Don’t make that my issue. Next, thing I have gathered is that you are quite comfortable in extending your offer. This means perhaps you’ve been successful…..perhaps…… perhaps.

Next, you suggest this in front of my friend. Bad move. We are asking ourselves as we look at your ridiculously: “Why would we even consider you for a mate/date, when you are so cheap?” All the real men please stand up! You’re rude, and you have no self-respect.

Finally, the fact that when I turn down the guy’s offer (because it was a bad offer), he made assumptions about me in an effort to deal with my rejection by making himself feel better. Yes, we all have experiences that shape and mold our likes and dislikes. But don’t insult me because you have issues with your own proposition being less than stellar!

I am already eating alone or with a friend, and happy about that fact I might add. Now I didn’t appreciate being put on the spot like that for one thing. Next, I did not like the fact that the only way we could talk is if we met at a restaurant, and we went dutch without it being something I offer or we at least have a discussion about. If you’re not able to take care of a lady in a manner that is respectful and safe, then you shouldn’t be pursing one. Women are bills. Period. If you expect us to be with you and you can’t even feed us, then think again! A meal is the best way to get a chance to know a person. You can let your guard down and dive into topics you can’t get into when you’re distracted with a bed in the house.

If you can’t afford dinner, suggest lunch (you can get a cheap lunch special at some really nice places), or just coffee and dessert. Stay in your lane, we appreciate that. We understand that at this phase of life it’s hard to find people who don’t have financial issues. That’s cool, but be honest. Don’t over/under extend yourself.


Date locations are everything

Date Locations

Don’t suggest a place where we have to think about whether or not there is a chance we will be assaulted or robbed. But also don’t neglect being thoughtful about date locations. The better the date, the more thoughtful you appear. Some of us ladies aren’t out for your pocket books. A good road trip, and beautiful scenic view, or a date in a romantic place (when appropriate) are nice ways to demonstrate how much you care and to illustrate genuine interest.


Finally, Smell Good, Please!

Smelling good is imperative. Come out of the 60’s middle aged men. Go to a department store and come into the 21st century. There is nothing like a good smelling man. We go through a lot to get ready for you on a date. Please do the same for us. Lots of doors (and legs) open for a good smelling man!

Those are just a few things that come to mind that are pet peeves currently. I realize I may be a tad bit picky but I also like what I like. Help me help you! No go forth and find your mature middle-aged woman and future companion.

Marley