I hear from men frequently who want to date older women and ask how to find/ attract/ approach the women they desire. I hear from very young men (teens and 20s) who had their first — and wonderful! — sexual experience with a much older woman and want to recapture the joy. I hear from men in their 30s and 40s who are drawn to the wisdom, experience, and beauty in women decades older. For example, TW wrote me recently:
I am a 41-year-old male. I don’t have any problem attracting women around my own age. That is fairly easy for me. But, I do have great difficulties attracting women who are much older than I am.
I am mostly attracted to older women who are in their 60s and 70s. I am not looking for a serious relationship. Just casual dating with someone I can see occasionally with the possibility of intimacy or sex. I don’t where to go to meet older women. I’ve tried some internet dating sites. The women on those sites respond by sending me an email telling me that I am too young or that they have a problem with the age difference.
I welcome anyone’s ideas and suggestions. Especially from men who have had successful experiences with older women. Also, I greatly welcome any suggestions from older women themselves.
Personally, I advise TW to get out and do the social activities he enjoys, where he’ll meet women who enjoy the same activities. That way, it’s easy to strart a conversation with a stranger because you already have something in common to talk about. Someone like TW would meet someone like me, for example, social dancing or at bookstores, coffee shops, gyms, walking trails, and vegetarian restaurants.
Once TW spies a woman who attracts him, I would NOT suggest the “Hey, you’re hot and I love older women, wanna go to my place?” approach. Instead, open the conversation with comments on the activity you’re sharing or ask her for advice, e.g., depending on where you are and what you’re doing,
“You’re a really good dancer — would you dance the next one with me?”
“Have you read any books by this author?”
“Your workout is obviously working for you — you look terrific. Do you recommend the aerobics classes here?”
And so on. You may be hoping to share the sheets with her, but you still need to show her that you appreciate more than her genitals. Remember that her most vital sex organ is her brain.
Readers, I invite you to add your own experiences and tips for TW. If you are a 60+-year-old woman who would delight in a fling with a man 2+ decades younger than you, how would you suggest that someone like TW find someone like you? (I’m not offering to play matchmaker, realize, just wanting to help TW know where to look.) If you’re a man who has had experience dating older women, please share your experiences.
You can post a comment here, or email me and I’ll post it for you. (Try to ride the thin line, please, between candor, which my readers like, and graphic details/street language, which they do not!)