November 9, 2013

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

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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Victor 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.

Sherri 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?

Allen 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.

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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!”