20 Suggestions for Younger Men Dating Older Women—Online. ~ Sherri Rosen

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Being what they call an older woman,  I’ve have been dating younger men for quite a while.  Here are some of my suggestions.

1. When you make the initial contact if it is just for casual sex that you are interested in please be upfront about it to save time on both sides. If you are straight forward it allows both of you to begin with the same expectations of sex.  If not it’s a waste of both of your time.

2. To introduce yourself don’t text. Texting is fine, I’m not against it, but when it comes to dating and meeting in the beginning, don’t text everything to arrange dating. It’s a real turnoff. Offer to call her on the phone.

3. If the woman offers to call you first, know that she is not afraid of making the first move and doesn’t conform to the traditional old ways. Also, for safety sake, many women prefer making the first call.

4.  Don’t tell her you look good for your age. Yuck. That’s the last thing she wants to hear. Tell her she looks great!. Period.

5. If it’s honesty and directness you are seeking, know that many older woman come out way ahead in this area. They have nothing to lose by being and showing who they genuinely are.   If in any way you meet and you see that she’s got the plastic surgery going on, has lied about her age, then you know where you are at with her.  And ask yourself if you want to be with someone who has totally misrepresented herself.

6. The older woman is used to dating. She was brought up that way.  She is used to being treated well.  Pay for her on the first date, even if she offers to pay her share.  You just seem really cool when you do that.

5. Communicate with her especially on the first date. Don’t make it an interrogation.  It’s uncomfortable for both, and there’s no way of having any kind of fun or spontaneous conversation.  If she feels you are totally into learning about her that is a real turn on, especially if you have a sense of humor.

6. Don’t mispresent yourself to her. If the picture you have online is what she will see in person, don’t come walking in looking nothing like your photo, either being fifty pounds heavier, the photo was taken when you were twenty years younger. Just like you don’t want someone to misrepresent themselves to you, don’t misrepresent to them.

7. She will want to meet you in a public place and allow her to make arrangements to meet, mainly in her hood. Again, it’s a turnon to a woman to have the man go out of his way to meet a woman.

8. If you say you are going to call her then call. If you can’t then text her and make a plan for another time.  Same goes if you are going to meet at a certain time, and you are going to be late, text her and let her know.

9. Neither one of you knows ahead of time where this will go. No expectations. The most important is in getting to know one another, having fun, being honest and upfront. Don’t say you want to see her again if you are full of sh*t.  If you cannot say it in person then send a short email.

10. There is no stigma to dating older women. Men have been dating younger women for ages.  But once you go that route if you feel uncomfortable don’t do it. And don’t do it because you are looking for a mommy. We’ve had plenty experience of raising children, we don’t need to be a mommy to you.

11. Know that many of us are quite experienced in relationships and we know how to treat a good man.

12. Always have a photo up on your profile site. No woman wants to respond to a ghost. Give us at least some sample of what you look like.

13. Please don’t make your profile sooooo long that it will totally bore us and even though you may look good, you will be passed by because of overwhelm.

14. Most cases if a woman doesn’t respond to your first response, it means she’s not interested. Don’t keep pestering her because it will come to an unhappy conclusion or blocking you from her site.

15. Many of us are confident, used to being alone and on our own, so don’t feel that we want to be with you every minute of the day, because we don’t. We are used to having lots of space in a relationship.

16. Hey men, if you are going to see a woman in another state for the first time, make sure you know what you are doing. You need to keep as safe and a woman does.

17. Many of us had much experience with BS and we know when it’s coming at us. Don’t try to impress but be real.  That’s very sexy.

18. We know at this stage about not changing the other person but accepting them the way they are. Be aware that if we see something ain’t workin for us, but working for you and we can’t work it out, that’s probably the end of the relationship.

19. If she’s desperate and is afraid of being alone, stay away, far, far away. Unless you are the same way as she is.

20. If you have children, don’t be afraid of introducing her to them. She has had a lot of experience in having fun with children.

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Editor: Dana Gornall

Photo Credit: Pixoto

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Live in NYC. Born in Baltimore, MD.  Was a gypsy with family living different places until we settled in Lynn, Mass.   Left for NYC at young age.  Was a performer. Now do standup Storytelling. Working now  as a book publicist and get to pick and choose my clients. Not only write for Elephant Journal, but my blog, Redheads Rap, and The Good Men Project. Have published 3 books all on Amazon. You can friend me on FB, Twitter and Instagram. Being in book publicity takes “hard work and magic!”

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anonymous Mar 11, 2016 1:26pm

I just came across this post…good advice for any man looking to have a mature relationship. I am dating an extraordinary woman who is 15 years older than me. I am 46 and she is 61. We have been together for five years and she is the sexiest, most giving and most mature person I have ever been with and I have been with many women…several much younger than me. All I can say to my brothers who may think the age difference is a barrier…don't. If she is curious about life, can keep up with you physically, and makes you happy…that's all that's important. If anybody has a problem with that…it's time to put on your big boy pants and ignore them.

anonymous Nov 12, 2015 3:51pm

Allen, just curious. If there is such a powerful connection between the tow of you why do you feel so out of place when it comes to relationships?

anonymous Oct 2, 2015 11:01pm

I met a woman, she is about three years older than I am. We are currently friends, although we have a great connection and great chemistry. I have been seriously thinking about dating her, although she says she doesn’t want to date younger guys. I feel like I am going to have to take it slow with her, because she is busy, especially with her having a daughter. I feel like things could really work out in the long run, and that’s what I really want. I have dated women my age and I don’t feel like we are at the same level in some aspects, such as future plans, etc. With her though, I feel like I could build an empire. I kind of have a feeling she knows that I have a crush on her, but I don’t want to tell her yet, for I feel that she’s being a little defensive on that front. We text almost every day whether we have seen each other that day or not. Friends of mine have told me that they can see there is a connection. Some days I don’t know what to do. I know I have to be patient, but there are days when i get so anxious that I feel like I should give up. I most certainly need help with this one. I have never felt more out of place when it comes to relationships.

    anonymous Oct 6, 2015 8:12pm

    Hi Allen,mi don't think it's the age difference, only 3 years, but do you feel you deserve a good woman in your life.

    anonymous Oct 7, 2015 5:09pm

    a three year age difference is negligible – no big deal. when I think of age difference it's more like a 10/12 or more years age difference.

anonymous Sep 18, 2015 5:02pm

I’ve been dating a younger man for awhile. We get along very well…both emotionally and physically… We are both in love with each other. However. Since I’ve been with him. I have received lots of negative feedback from family and friends.
It does bother me to think that they think we are both…weird… I just wish that our society would be more accepting of ..older women and younger men…like they are of older men..younger women. If it works..why not . I’m very happy with him….im widowed and I feel like I’m blessed to have found love once more in my life

    anonymous Oct 6, 2015 8:09pm

    Anna Marie enjoy yourself. I've gotten negative feedback also but told my family I don't want to close down age difference and prevent me from meeting someone special. Not many get it unless in similar situation. If you are happy that's what matters. Sherri

anonymous Sep 6, 2015 12:52pm

im dating a 29 year old women and im a 26 year old man… i really like her.. we been daitin almost 2 months.. and shes very busy.. but ive done very nice things for her.. we just haven't done it yet.lol.. but its not about that… i want things to work out well, and she has a kid thats over 10.. should i just let things fall into place and keep it simple.. and be real and not try hard at all.. shes an awesome woman and person, should i just continue to keep things simple?? she defnitley likes me… we been talking prety much every day…help is wanted

    anonymous Oct 6, 2015 8:15pm

    Hi Brad just take it slow and see where it goes

    anonymous Oct 7, 2015 5:12pm

    again, a three year age difference is no big deal – however, sometimes problems arise when it is a 10/12 or more year age difference. you really don't need help, just be yourself.

anonymous Apr 9, 2015 6:14pm

Do not make fun of the great women in age.
May intervene in the case of depression

anonymous Apr 6, 2015 7:25pm

I am dating a Japanese woman 12 years older than me. It is a unique situation compared to others because despite the age gap there is no difference than there would normally be between two people with culturally different backgrounds. There is no real generation gap problems because everything she grew up doing is completely different than anything I did while growing up..

It is an interesting experience.

anonymous Mar 22, 2015 3:05am

Hi Again! I forgot to post the link to my other EJ article on Ripe: Aging With Grace & Authenticity (with some nudes). Again don't buy into the bs that media and culture tells us we should look like. Fall in love with you!!!

anonymous Mar 7, 2015 6:29am

It's so funny. There is no term for an older man. Just older man, but with older women, they have to label us a Cougar. It's actually funny and sad at the same time.

Checkout my latest story in EJ: Called: Ripe: Aging With Authenticity and Grace. EJ did a fabulous job with the text and the nudes. Proud to be part of this type of journalism. And the comments are not out to destroy you. I'm sure EJ would take them down if they were.

Enjoy your life however you choose to live it!!!

Ageism like Racism is so embedded in our culture. Media has taught people to feel negative about their aging and as a result it's mind blowing that so many women have taken in the negativity. Got to begin somewhere so I felt posting the article above and this article was a step in the right direction!!!

anonymous Jan 8, 2015 4:03am

I want a older lady for till end of life.
coz she will be experienced about life, sex & everything. But she will be reliable.
And charming.

anonymous Dec 14, 2014 4:55am

I’m a 24 yr old guy, & ever since i was 19, the younger women never wanted a relationship or the kinda love i want. Plus most of the younger women had bfs or they was immature & detached (emotionally). i had crushes on But i met a few older women in my life, even tho some had ughboyfriends, they were super sweet to me. I usually run into them at church or college. I just feel so at ease with older women. They are easy to talk to about anything. Older women that i met are very smart too. They know a lot, & that’s very attractive & respectable. Not that i’m dumb lol. But i just feel older women offer everything i always wanted in a girlfriend. I find them more caring, dependable, & they probably would appreciate a good man who will care for thefs, always & respectfulat my Not to mention, most older women that i have seen look wayyy better then some of the women my age. Older women know how to dress. I like the classy look & older women have great style. Now i would never ever date an Older woman for just sex. I would want more than that. I want love & deep care first. I would wanna be with an Older woman forever. I don’t want an Older woman for her money either. I rather get my own money. I want a older girlfriend for her, her love& . I don’t think most young women would like the kinda relationship i want. So it’s not just about sex with older women. I love them because of their whole presence =). Sorry for the long story lol

anonymous Dec 3, 2014 12:38pm

I meet sexy older women

anonymous Oct 29, 2014 4:39pm

If you don’t want to be called a Cougar then don’t be one.

anonymous Aug 9, 2014 5:36am

I’ve always been baffeled at the different expectations between men and women, boys and girls. I am 37 and realised a few yrs ago, its all about timing. Eg… Teenage girls: most,fall in love with the first boy who comes along and the boy is wanting sex. Most boys, continue to have as much sex, with as many as he can and then hits late 20s 30s knowing what he’s looking for.

Now, us girls, during these yrs, are left broken hearted, and feeling unappreciated and un loved.

But then…. Something snaps in the now, womans brain. She’s 22-26 thinking how she’s wasted time on ‘needing’ a relationship so bad that she’s forgotten about how fun sex is!!! So she becomes like that 15yr old boy!!! Using men as they once used her. By the early 30s she’s now beginning to know what she wants, but she’s broken a few mens hearts along the way. By now, she’s independent and thinking of settling down… properly.. But the men her age now are hitched, got baggage or divorcing..

So, as i was saying about timing…

It makes more sense a younger man with an older woman…

Its always seemed and been more accepted, older men with younger women.. But how is that relationship mature, based on timing?

Now i know there are exceptions to every rule.. Love is love..

Dont let age hold you back… 🙂

anonymous Jul 14, 2014 9:54am

I've been dating this younger man for about a year and it's different; no seXhas occurred but there is interest so where so we go from here? There is a twenty year difference. I can deal with it, but, he having more issues with it than me. ….any advise?

anonymous May 21, 2014 7:26pm

YES! YES! YES! I also love an older woman who is an excellent. And, i want to learn as much as i can, so i can go forward with her, not messing things up, that turns her off. Thank you very much for your help.

anonymous May 21, 2014 3:54am

Thanks! I've recently only started talking to an older woman who is truly beautiful, and just trying to prepare myself the best way possible not to screw it up – found this article really helpful.

anonymous Apr 15, 2014 10:40am

Want to let people know I do not like the word cougar. The word is negative sounding like aggression, and many older women are swwet and sexy like I am.

    anonymous Dec 27, 2015 8:47am

    Sherri Rosen, you are right calling a woman or women cougar is an insult that is what I believe, it is similar to " LIKE " some will say I like this or that woman well she is not a material nor a shoe, instead males should tell women the want them..
    Sherri you are wonderful..

anonymous Apr 15, 2014 2:53am

Now,many older women want to find younger men,they needs some tips about it .Maybe website is a great way to do it. Recently,I find a young life mate by a site ,he is good-looking,wealthy …Thanks for that site .recommend to you: http://meetacougar.org, good luck

anonymous Apr 6, 2014 4:42am

I actually enjoyed reading the points given and I feel like reading it again.I’ve always liked older womem.

Some age gracefully ofcourse and while others are intellectually gifted and all have their own stories to tell.