Sherri Rosen offers some advice to younger men who are interested in dating an older woman.
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Being what they call an older woman, I 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 casual sex that you are interested in please be upfront about it. If you are straightforward it allows both of you to begin with the same expectations. If not it’s a waste of time for both of you.
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 old traditional 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.
6. The older woman is probably used to dating. She was brought up that way. So if you pay for her on the first date, even if she offers to pay her share, you’ll be showing respect. 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 misrepresent 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 50lbs heavier or if the photo was taken when you were 20 years younger. This obviously goes both ways. Just like you don’t want someone to misrepresent themselves to you, don’t misrepresent yourself to them.
7. She will want to meet you in a public place. Allow her to make arrangements to meet, mainly in her hood. I notice it’s a turn on 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. The 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 end up boring us because we can’t get through it, 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 contact, it means she’s not interested. Don’t keep pestering her. Even if she ultimately engages, it will come to an unhappy conclusion or result in her 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 as 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 excepting them the way they are. Be aware that if we see something ain’t working for us, but workin for you and we can’t work it out, that’s probably the end of the relationship. It’s more fair to do that than to try to change the other person, do you agree?
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 — assuming your children and you are comfortable with meeting people you are dating. Chances are, she has had a lot of experience in having fun with children.
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Photo: AP/File
I like what I have read so far and frankly speaking I had really like to meet and date a lady if I am givivng the opportunity by any who doesnt really think the age thing is a barrier.
I am a 20 year old guy,and I am so into it meeting,dating a older woman 🙂
You can follow older women dating younger men on @ the Cougarist : http://cougarist.blogspot.com
Male, low 20’s. I’ve been waiting to be in the age range to date women in their older 20’s for a few years now, so this article caught my eye. Good suggestions. I’m not sure it addressed one of my biggest issues though. I’m quite accomplished/successful when normatively compared to my peer group. As such, since men are often regarded as “success objects”, I find it too easy to impress women my age and certainly younger ages. It leaves me with a feeling of being desired simply for being successful and not for who I am as a sentient man… Read more »
Come on men. Join in the conversation. Appreciate your feedback.
I love this Sheri. Thank you for writing it. The only one I disagree strongly with is #7. While I may indicate some options for places I’d like to meet (e.g. a wine bar), I want the man to do the work of arranging it. I’ve learned that if I’m the one who makes arrangements for the first date that sets the tone for the rest of the relationship where I’ll be the one doing all the work. No thanks.
Thanks TAG for your feedback. Yes, I get that, but this is what works for me for first meeting someone new. Nothing is set in stone. Just suggestions. You need to do what works for you.
Only female comments so far… interesting! I really appreciate these dating guidelines and feel that they are good FOR ANY AGE. I have extensive online dating experience (although I would prefer to have less!) and have experienced older men as the most arrogant and least flexible out of the age stages…very unappealing qualities. It’s a great pity. I’m in my forties and not desperate, but increasingly disillusioned by ‘age appropriate’ partners. Perhaps younger is a better option…
Ok looks like I’m the first man to respond. I have found what you have said about men in your age group to not only be true of my fellow men but women my age can act the same way. I have dated younger women and found they can be more mature. On the other hand, there comes a point where the proverbial “generation gap” can come into play. My experience with younger women has decreased my arrogance (not that I had a lot haha) increased my flexibility. At some point, I realized I would prefer women closer to my… Read more »
Hi Paul,
Thanks for being the first man to jump right into the discussion. Appreciate it.
Yes, you are right these 20 suggestions for Younger Men Dating Older Women can go for men and women, and probably for all ages, but I wanted to put it from my own perspective and share some of my experience because I haven’t read too much about the Younger Men Dating Older Women.
And, even with all of my experience dating I cannot tell you what will definitely work because like others I am a continuous work in progress.
Kim what I try to do is to stay open and not make judgements on a particular age group. Who knows when that right person will come along, and how old they will be. I just no longer have any expectations, but keep the door open. Thanks for your feedback.
THANK YOU for this! I am an older woman who gave a younger man a chance, despite it NOT being what I was looking for. My boyfriend and I have been together almost a year and it began with a simple email from him on an online dating site. One of the first things he wrote caught my attention, and not only because it showed he truly *read* the specifics of what I was after: “I understand that I am younger than you state the minimum age you are interested in, but I ask that you give me a chance… Read more »
Penny, right on! So happy for you that it has worked out. As you can see by one of my other responses I do not like the label Cougar. The media makes up this BS to increase viewers/listeners/readers, and a lot of folks by into the BS. In any event, appreciate your sharing.
I am in my early 40s and have been online dating for several months. Although I have tried to stick to the seven up and seven down rule of thumb when dating, I have found myself going sometimes ten years down instead of seven. These are great suggestions for men considering on dating an older women. By the way, one of the biggest turn offs in dating an older woman is referring to her as a cougar and you as her cub, and yes please do pick up the phone every once in awhile.
Hi LovejoySD
Please do not use the word , older woman for a woman in her early forties!
Today we can live until our nineties and some even become older than 100.
Do men see you as ” an older woman ” when you are in your early forties or is it how you see yourself ?
This is a terrible way to see yourself .
Hi Again LoveJoy-in putting this article together, that’s what I came up with, because that’s what I am, and older woman. But I am not telling anyone if they write their own article what to refer themselves at. It’s up to each one of us to define who we are, not so much with labels but how we are in our life. And no, men get quite shocked when they find out what they true age is. They don’t believe me when I tell them the truth Ha-Ha. I think that’s great!! I know who I am so anyone including… Read more »
Hi Kim,
Thanks for pointing that out concerning the term “older woman” I was just replying to Sherri’s post. I’m 41 years old and have been dating someone for a couple of months who is 31. Although him and I have ten years between us, I feel like I am as young as he is. We have the same energy level, and enjoy the same things and activities. It has been wonderful! So I agree let’s throw the term “older woman” out the door!
Hi Everyone!
Thanks for all of your great feedback, but we need to hear from some men out there.
Would love to hear some guys responses to the article.
Hi LoveJoySD,
Appreciate your article. Yes, that’s one thing I forgot to put into the article about being called a Cougar. It gives the description of a woman who will eat you up alive. Yuck.