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

Via Sherri Rosenon Nov 8, 2013

Photo credit: Pixoto

Being what they call an older woman,  I’ve have been dating younger men for quite awhile.  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.

Like elephant love on Facebook.


Editor: Dana Gornall

Photo Credit: Pixoto

About Sherri Rosen

Sherri Rosen is now living in Harlem, New York. She has had her own publicity business for 12 years, giving a powerful voice to people who are doing good things in the world. She writes her own blog.


Loved it? Leave a tip!

(We use super-secure PayPal - but don't worry - you don't need an account with PayPal.)

13 Responses to “20 Suggestions for Younger Men Dating Older Women—Online. ~ Sherri Rosen”

  1. ken says:

    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.

  2. wymlilina says:

    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

  3. Sherri Rosen says:

    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.

  4. Mike says:

    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.

  5. Johnnie Moore says:

    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.

  6. Gail says:

    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?

  7. Jen says:

    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… :)

  8. Janice says:

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

  9. mahe says:

    I meet sexy older women

  10. Georgio says:

    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

  11. Virendra says:

    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.

  12. Sherri Rosen says:

    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!!!

  13. Sherri Rosen says:

    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!!!

Leave a Reply