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Dating Older Women

It doesn’t matter how old your date is, after all, age is just a number. What matters most is open communication and compatibility. You should show the same respect to an older woman that you are dating as you would to a younger woman. Here are a few tips to keep in mind when dating a woman who is older than you.
 


Understand the generation gap. You were probably a freshman in high school when she was a senior, but that doesn’t mean you didn’t experience the same music and movies. She might sound a bit more experience than you but that’s okay, just don’t use her own words to tease her about her age.

Give genuine compliments. Although she probably has had more dating experience than many younger women, she still might feel a bit insecure. Therefore, giving genuine compliments about her hair, her clothes, and so on will make her feel comfortable and assure her that she is very attractive and appealing to you.

Don’t bring up the past. You might think that you are being funny by making fun of her past husbands or relationships, but you might remind her of a harsh past of a guy who didn’t know when to stop. If she is uncomfortable talking about her past relationships or marriages, don’t pressure her to talk about them. Instead, bring the conversation back to a more pleasant and light topic.

Be yourself. You might lack experience that your older date has, but she chose to go on a date with you regardless of the age difference, so the age gap shouldn’t matter to you either. You don’t need to act more mature but at the same time, don’t take a step back and become immature. There is a special quality in you that attracted her so be yourself, show true compassion, and let her learn more about who you are.

Be a gentleman. It might be a bit difficult to win over her friends and family members being that you are younger than her in their eyes, but if you act maturely and treat your older date like a true gentleman, you can win respect from her friends and they will be able to see true compatibility between you two. Remember that they understand her past better than you do so don’t be afraid to take things a bit slower than you would with someone younger.

Use this tips if you are only serious about making a long lasting successful relationship with an older woman. If you are looking for someone just to say that you’ve been out with an older woman, then it might be better for you to stay with someone your own age.
nov 3, 2011 | Comment (60)

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Marcus Lira, 36 Mar 24, 2011
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I've never been attracted by the idea of dating a woman who is much older than me. I think it's abnormal, why not dating young pretty girls with young bodies? I don't want to offend anyone but older girls should date older guys...

Lillian, 31 Mar 24, 2011
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well i wouldnt say i "date" anyone, but yeah, there have been some older ones, and they fall into 2 categories - 1) the ones that instantly want to get married and go absolutely ing bananas that i dare not want them, and 2) the ones who have either given up on finding a man to commit to them the way they want or are recently out of a relationship and so are jsut interested in company in sex. those in category number 2 are awesome, theres very little downside to knowing them.

Mauro, 36 Mar 24, 2011
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I'm not sure if this is my ADD but I always seem to be attracted to older women, I'm 23 and the women I always date women at least 10 years older than me. They are much more sensual I find and don't play games. And moreover they are great talkers - they are experienced and willingly share their experience with the partners, so such communication brings not only pleasure but also some intellectual benefits.

Kattyaragonez, 29 Mar 24, 2011
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The same woman at 20 that is 40 and twice your age will not be twice your age even in just 1 year. So chances are you won't find a lot of that. I was with a 46 year old. I did a lot of things wrong as far as maintaining the relationship but in the end she wasn't worth it anyway. Sex was great though. I don't know if it's something about that age or what but she definitely had a good attitude towards sex. Something that bummed me out though....I thought there was no way a 46 year old would still be playing games at that age but I was wrong. If you get with someone that old forget about them being anyone else than what they show you, they are set in their ways. I would definitely do it again but approach the non sexual stuff much differently.

1 reply | Hide
Harry, 36 Mar 24, 2011
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My experience was the same. I was 24 when I dated my first lady (40). I've always had a thing for older women, especially when I was younger...it must have had something to do with my high school years and always wanting to screw the teachers I was attracted to. With those women, I just screwed them and left them or never heard from them again. Then back in 2008, I dated a 40 year old for 1.5 years and for the life of me, I don't know how I let it go on for so long and how I developed oneitis for that chick....sh*t still haunts me. Can't say I won't do it again, because I still have that damn fetish in me but if I ever end up the situation again, I'll just pump em and dump em.

Mondaymerry, 34 Mar 24, 2011
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All I can say about relationships with older women is "don't". Screwing a couple of cougars is fine if you're young. It'll give you some experience. If you're young you'll bang anything anyway, so who cares if she's not a 19 year old hottie. But older women aren't good relationship material, especially not for younger guys. They have baggage and issues. If you give them a chance they'll try to lay this on you. So when it comes to older ladies - just DON'T

Lhanray, 36 Mar 24, 2011
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anyway, guys i see here more pros than cons - An older woman is more often more independent, knows what she wants in life and has an established career. She will be selective about when she spends time with you, which means a relationship where you will have more time to do your own thing. She will be less ‘needy’ and understand the importance of quality vs quantity. An older woman is more experienced. This is a great thing as there is always much to learn about culture, wisdom, and all that other good stuff that only an experienced person can have. You will find yourself less at the local pub on a Friday night, and more at classier places like nice restaurants and the theatre. Expect the intelligent conversation to pick up.

1 reply | Hide
Frank, 33 Mar 24, 2011
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yeah... An older woman is less likely to ask you to pick up the check for dinner. She will have her own money, be more confident in her self and is less interested in ‘traditional’ date behaviour like that gentleman picking up the check.

Jane, 26 Mar 24, 2011
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IMHO situations differ with each individual and what might be true for some may not be true for others. My sole interest in writing this article (and others) is to assist people in finding relationships that are happy, and not to make generalisations or cause offence. I'm happy I'm not an "older" woman" yet but when I grow more mature I don't want to be commented like this...

Jane, 26 Mar 24, 2011
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If you like her and she likes you then go for it. If she's cool with it and you're cool with it, then it's alright. She's right. Age is just a number, but there is such a thing about being in two different maturity levels in life. If you guys can relate to each other on the same level, then it should be a successful relationship. Age will never be the limit for me!

Frank, 33 Mar 24, 2011
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My friend is 23 his lady is 45, she has a son a year younger than my friend is! I don't beleive their relationships have any future... She's a business woman and has no time and desire to meet with his friends, they have different interests and I don't really understand what unites them, besides sexual relationships of course... moreover he's cheating on her from time to time. These is obviously distructural relationship....

Grahamstuart2, 38 Mar 24, 2011
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i've had this thing too with older women..the sex part of it is just out of this world but then now it comes with their "life baggages"..which in turn u wouldnt want that kinda sh*t hangin around your neck,,,,i havent gone thru that phase though i still fancy them

Ralph, 34 Mar 24, 2011
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Funny how some people assume that younger people don't have "baggage." It may not come in the form of a job, kids and an ex-husband, but isn't college stress, parental involvement, multiple-sex partners, and still figuring out what to be when you grow up and how to support yourself a form of "baggage" as well? It's just called immaturity.

Joe, 33 Nov 3, 2011
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A man in his mid-twenties who dates a woman in her early or mid-thirties will go through an enriching life changing experience. Your average twenty-year-old woman is energetic, ambitious and out to get things done. Now, you take a woman in her thirties, chances are she's lived a little more. She's learned that the world isn't all it was cracked up to be, and she's less likely to be over-enthusiastic about driving twenty miles to go to dance clubs that charge a twenty dollar cover and serve cherry flavored water. This is actually good because most men become lazy when they fall into the hands of a woman.

9 replies | Hide
Frank, 33 Nov 3, 2011
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you'll never find a rose without a thorn. This means that in exchange for peace of mind, you have to be willing to accept some of the implications that come with dating an older woman. More often than not, however, the advantages overwhelmingly surpass the drawbacks.

8 replies | Hide
Catherine, 32 Nov 3, 2011
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Older women may not be as toned as they once were and they might not be quite as perky in the various spots they're supposed to be perky in, but it's amazing what an extra ten years of experience can teach you. They don't beat around the bush (they let you do that). They know exactly what they want and they will manipulate you physically and mentally to get it.

7 replies | Hide
Ibou, 36 Nov 3, 2011
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A man is terrible when it comes to taking the time and effort to figure out what a woman really wants. An older woman has learned not to waste precious time waiting for the man in the shining armor to sweep her off her feet. She has accepted that it "ain't gonna happen," and she will let you what to do and where to do it.

6 replies | Hide
Adam, 31 Nov 3, 2011
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Older women are more established in their careers and rely less on a man to support them or a potential future family. An older woman's independence is a strong stress reliever for any man. A man does not have to worry about dating young gold diggers that will take him for a ride only to get a slice of his wallet. This takes away some of the pressure from a man's shoulder to support the relationship (i.e. you won't go broke).

5 replies | Hide
Peter, 32 Nov 3, 2011
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A word of caution, this point does not apply to all older women. A young gold digger will eventually become an old gold digger, so keep your eyes open. At an older age, a woman should have the ability to pay for her own things (i.e. furniture, clothing, cell phone, etc).

4 replies | Hide
Candera, 30 Nov 3, 2011
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Older women know how to appreciate the truer things in life. They don't play head games and don't value the materialistic ideals that are pushed through the media channels. You can have a deep conversation with an older woman, and not have to worry about going into stupid topics such as how her hair follicle no. 490 was out of place, or how the pink lipstick did not match perfectly with her purple mini skirt. You also don't have to worry about returning her home before midnight to meet a curfew.

3 replies | Hide
David, 35 Nov 3, 2011
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The benefit of older women is especially apparent on vacations. Young women have the annoying habit of wanting to always wanting to do something. They say silly things like, "We paid all this money to be here, we should make the most of it." This is a phrase that no man in his right mind ever wants to hear. A man goes on vacation to drink over-priced beer while sitting in a Jacuzzi contemplating what to order next at the all-you-can-eat restaurant.

2 replies | Hide
Jilly Pattins, 33 Nov 3, 2011
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There's nothing wrong with a May/September relationship because a woman has as much right as a man to like someone younger. To find that perfect older woman, you might have to consider her plans to start a family. Remember, her biological clock is pounding real fast. Since she wants to date a young man, however, there might be a chance that she just wants to have fun with an energetic man without having to worry about having babies. So before jumping into a relationship, find out if she's looking to have kids right away.

1 reply | Hide
Emma, 30 Nov 3, 2011
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Along with those great years of sexual experience, some unresolved issues and excess baggage come attached to the package. You might want to consider doing a credit personality check to make sure she has no femme fatale history.

Polly Kullmann, 24 Nov 3, 2011
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Common sense dictates that you cannot be 40 years old and single, and not have a significant amount of baggage. Ex-boyfriends, husbands, children, ex-step-children, pending divorces, business pressures, financial obligations, and debts can often be part of the package.

4 replies | Hide
Daniel, 34 Nov 3, 2011
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yeah right. You must be ready and willing to accept this reality if you are going to get romantically linked with an older woman. This is not to say that you will be asked to deal with these issues per se; rather, you must realize that an older woman generally has more to worry about than that bushy-tailed co-ed at your dorm.

3 replies | Hide
Catherine, 32 Nov 3, 2011
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One cannot deny the allure of the older woman, younger man relationship. But, this relationship remains slightly taboo, unlike the other way around, where the man is much older than the woman, which is perfectly acceptable. After all, no one raised an eyebrow when Catherine Zeta-Jones married Michael Douglas.

2 replies | Hide
Daniel, 34 Nov 3, 2011
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Like it or not, by getting involved with an older woman, you are putting yourself in a situation where the moral majority -- people like your parents and boss -- will frown upon you. On the up side, you may become your buddies' hero, and they will start begging you to reveal what it's like.

1 reply | Hide
Catherine, 32 Nov 3, 2011
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In any case, people will talk. If you are secure enough in the relationship, or you actually like the attention, then by all means, proceed.

Hurtinghubby, 36 Nov 3, 2011
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Often, older women are newly divorced, and looking to sow their wild oats. Getting involved with a man who isn't looking for a serious relationship and wants to have fun is the perfect solution.

4 replies | Hide
Deborah, 34 Nov 3, 2011
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Younger men have the stamina and carefree attitude to satisfy their need for a wild ride. So, if you're looking to learn a thing or two between the sheets, look no further than an older woman. After all, she's no longer sexually inhibited, knows what she wants, and probably has a few tricks up her sleeve.

3 replies | Hide
Daniel, 34 Nov 3, 2011
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More often than not, an older woman has faced her insecurities and fears head on, and has dealt with them to the best of her abilities. She likely has enough life experience to know what matters and what doesn't. Consequently, she's above the petty nonsense that drives you crazy about women your own age. An older woman has figured out what makes her look fat, and what looks good on her, and knows enough about male-female relationships to not bother you with feminine trivialities that usually serve to turn men off.

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Judith, 31 Nov 3, 2011
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Older women have the self-confidence that could only come from experience and the knowledge that they can handle whatever life throws their way. That is not to say that they never have a bad day, but merely that it's probably due to something more than the fact that they have a pimple and a party to go to that night.

1 reply | Hide
Catherine, 32 Nov 3, 2011
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the promise of mind-blowing sex with an experienced, confident woman, without the expectation of a long-term commitment -- I know, it's a tough call.

Angelagrahamii, 19 Nov 3, 2011
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older women are not only more mature, and financially independent, but they're also better lovers and usually won't mess with your head. These are just some of the positive aspects of dating an older woman.

3 replies | Hide
Lady Girl, 28 Nov 3, 2011
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A man in his mid-twenties who dates a woman in her early or mid-thirties will go through an enriching life changing experience.

2 replies | Hide
Catherine, 32 Nov 3, 2011
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Your average twenty-year-old woman is energetic, ambitious and out to get things done. Now, you take a woman in her thirties, chances are she's lived a little more.

1 reply | Hide
Judith, 31 Nov 3, 2011
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She's learned that the world isn't all it was cracked up to be, and she's less likely to be over-enthusiastic about driving twenty miles to go to dance clubs that charge a twenty dollar cover and serve cherry flavored water.

Babbit, 36 Nov 3, 2011
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Older women may not be as toned as they once were and they might not be quite as perky in the various spots they're supposed to be perky in, but it's amazing what an extra ten years of experience can teach you.

2 replies | Hide
Bethany, 28 Nov 3, 2011
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They don't beat around the bush (they let you do that). They know exactly what they want and they will manipulate you physically and mentally to get it.

1 reply | Hide
Craig, 35 Nov 3, 2011
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An older woman has learned not to waste precious time waiting for the man in the shining armor to sweep her off her feet. She has accepted that it "ain't gonna happen," and she will let you what to do and where to do it.

Wahab Nurudeen, 36 Nov 3, 2011
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Older woman seduces younger man.

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Catherine, 26 Nov 3, 2011
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But high-profile Hollywood couples like Susan Sarandon and Tim Robbins (12 years her junior) -- who met and began dating while filming an on-screen romance in the 1988 movie "Bull Durham" -- have proven that life can indeed imitate art when it comes to matters of the heart.

Brenda, 33 Nov 3, 2011
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There's a new creature stalking the urban jungle – the cougar. She's a woman in her forties or fifties, on the hunt for younger men.

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Counselling London, 36 Nov 3, 2011
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But before becoming too judgmental, let's look at the biological facts. The male of the species hits his sexual prime in his late teens, a woman in her late forties. You

3 replies | Hide
Penelope, 29 Nov 3, 2011
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19 goes into 50 a hell of a lot more than 50 goes into nineteen.

2 replies | Hide
Gah, 36 Nov 3, 2011
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I once dated a boy ten years younger than me and only lab rabbits had more sex than us. We had phone sex – but in the booth.

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Lillian, 31 Nov 3, 2011
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Great sex is about inhibition. And once a woman has endured the indignity of the birthing ward, what could ever embarrass her again

Sasha, 29 Nov 3, 2011
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By contrast, younger women are so insecure. They worry about breast size, body shape, cellulite, weight – they order one crouton for lunch and then share it.

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Robert, 26 Nov 3, 2011
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An older woman, on the other hand, is so much more relaxed in her skin. Once a woman hits fifty, a liberating "now or never" mentality takes over.

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Catherine, 32 Nov 3, 2011
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Forget breast implants and botox and get a dimmer switch – the greatest sex and beauty aid known to womankind.

Betty, 26 Nov 3, 2011
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I married somebody slightly younger than me and have recently ended a 3 year relationship with a guy 3 years younger. You know what? It's exhausting! I don't want to be raising somebody else's child and either I picked a very faulty specimen or the whole idea of sex non stop is just a big fat myth! It's down to the individual as opposed to specific age although yes, being in your 20s / 30s does help! On the other hand, right now, there is nothing that appeals more to me than a very well respected male, well in his 50s (20 years older than me), who works out and embraces life! Now, that's what I call a man!!!

Angie, 25 Nov 3, 2011
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Discriminating against age is just as bad as discriminating against race, height, etc... If two consenting adults want to date each other than who am I and who are you to tell them how to live their lives? Older men can date younger women and younger men can date older women, it's a free society.

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Daniel, 34 Nov 3, 2011
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So long, as both are consenting ADULTS. I've seen 30 something year old women who look 10 to 15 years older and some older 40 something women who look better than 20 something year old women... Ageing depends on your environment and lyfestyle (health, exercise, clothing, hair style, attitude, overall presentation...)

1 reply | Hide
Michael, 36 Nov 3, 2011
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I personally believe that I have a duty of care and an obligation to look my best and it would be disgraceful and shameful to let myself deteriorate due to neglect and bad decisions (heavy drinking, smoking, high caloric intake, etc...) So before we start judging others, lets all take a look in the mirror and judge ourselves first. :-)

Hughbredberry, 33 Nov 3, 2011
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I have to say that I've read a lot of ridiculous things in my life but this cougar crap takes the cake. Let me spell it out for all you ladies young and old and it won't take an entire article to do it: The ONLY reason any man would have sex with a woman 10-25 years his elder is because he can't get a women 10 -25 years younger than he is!

Hughbredberry, 33 Nov 3, 2011
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Why would an older woman -- especially one as beautiful as Sophia -- want to be seduced by a younger man? Well for starters, she wouldn't have to worry about me using her. Quite the contrary, I think I should have been worried about her using me for my body.

Sherry Moore, 39 Nov 3, 2011
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It is not the age of a woman that matters it is her attitude. If she is 20 or 50 if she is witty secure in herself she is attractive and can have whatever she wants.

1 reply | Hide
Frank, 33 Nov 3, 2011
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We are living in a western world where we are free to choose whatever we want. think of the other societies that we are living alongside and how restricted their choices are either through poverty or politics.

Amit, 30 Mar 16, 2012
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i dated 30 when i was 20 had entire Night with cup of coffee. lol good experience,,

1 reply | Hide
Jonathan, 32 Mar 19, 2012
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yep, man - totally agree with you, women in their late 20-s or early 30-s are damn hot - they know what they want and how they want it!

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