22-year-old man: "How to approach older women?"

Jan. 23, 2016 update: I'm bringing this older post up to the top again because of all the questions I'm getting on this subject. I get more emails from younger men -- mostly age 18 to 30ish -- who are attracted to older women (usually 60+) than any other topic!

So I'm resurrecting this post and inviting comments from both young men about what attracts them to older women and from older women about how a younger man can find them and make contact. Are any of the online dating sites especially good to help younger/older connect?

Note: I am NOT matchmaking here, though many young men have begged me to post their email addresses or phone numbers. No, I won't do that. And guys, please don't ask me personally to hook up with you! That kind of request -- yes, I do get them -- feels creepy, and I won't even answer to tell you to stop it. Just stop it. And no, I don't want to know how big or hard your penis is or how long it can perform -- and I really don't want to see a photo of it. Just. Stop. It.

So, that said -- most of the people who ask for help are sincere, respectful, and sensitive to their partner's desires and pleasure. Realize that our age and experience has not turned us into an alien species -- treat us like valued human beings, interesting for more than sex. And please see other posts on this topic here.


Leopardy is a 22-year-old male in Australia who likes older women. He emailed this story to me:

I've had 2 women in my life (sexually only). Great fun, I must admit, but it tears you apart when the bad has to come up. I like older women for their maturity and for their gorgeous features, such as lips, hips, legs, and fragrance, mmmmmmm. I admit I find it rather hard to find the perfect older woman as they all tend to lead me on then shoot me off which hurts like hell.

I met a woman online back in 2004. After 3 months chatting I gave her my details and she came up here. We had sex, and then she really got abusive and threatened me with police threats etc. She told her so-called friends about me and said what a pathetic useless peice of shit I was.

I'd like to know how to approach older women. I just want a woman that can understand me, one that takes me for who I am and NOT degrade me in any way.

Thank you for been so supportive and having a wonderful site. I can't even recall how I got hold of your site, but I was amazed and immediately added it to my favourites.

Leopardy, I encourage you to get to know the older women who attract you before you jump into bed with them. Those who are looking for quick fun probably won't value you the way you want. It's fine to seek a match online, but if you seem to connect, please take some time dating and becoming friends so that you know who she is and she knows you.

That might mean you don't get the instant pleasure and excitement of sex with a stranger who seems to fit your fantasy, but if what you're looking for is a respectful relationship, that takes time to unfold and nurture.

That doesn't answer your question about how to approach older women. I'll repeat the suggestions I gave Sean:

1. Converse, listen (very important!), and flirt as you would with a woman of any age. Yes, she'll recognize the signs. She might be shy about letting you see her signs, in case she fears she's misreading yours, so keep her talking.

2. Don't rush things along -- she wants to know that she interests you as a person, not just a potential bed partner.

3. Look into her eyes a lot. Really listen and respond to what she's saying.

4. Lean towards her to give the body signal that you're interested. Watch for these signs from her: eye contact; leaning towards you; arms relaxed (not crossed in front of chest); playing with hair, clothing, or jewelry.

5. After a nice, long conversation, where you feel there's a connection, you might ask her outright: "I wonder if there's any reason I should not ask you out."

6. If she says, "I'm old enough to be your mother," you can ask, "I really like the maturity and intelligence of older women. The question is, am I too young to interest you?"

7. If you're really brave, carry a copy of one of my books. When she asks about the book, say something like, "I find older women very attractive, and I hope this book will help me understand them better -- in all ways."


I'd love to hear from readers about this topic. I know many readers come to my blog seeking information about older women/younger men relationships, so please contribute yours.

-- Joan

Me, Dan Savage, and Two 70-year-old, Lust-Crazed Cousins

8/19/14 update: I originally wrote this post on June 25. I'm moving it to the top of my blog because I'm a guest on the Savage Lovecast episode 408 that airs today, and I expect many Dan Savage fans to visit this blog for the first time out of curiosity. In the 8/19 podcast, Dan refers to a scolding that I gave him. This blog post is the scolding/ spanking he's talking about. Enjoy! 

"Joan? Too far outside your wheelhouse?" began Dan Savage's message to me. He sent me an email from a reader who wanted advice. Because the reader was 70 years old, Dan thought I'd be the right person to help him respond.

Here's my interpretation of what I read:

A 70-year-old woman has been crazy with lust over her female cousin for the past 50 years! It turns out, the cousins discover now, that they both feel the same way! Bring it on! But since they're both inexperienced in the ways of lesbian sex, they decide it would be cool to get a third woman in on this, to guide the experience so that the first time is stellar. Their fantasy is that Cousin #1 would watch Cousin #2 and their #3 at first, then join in.Their question: How to find this third? 

What did I actually read? This:

I'm a bit out of your demographic, agewise (I'm 70), but I am still an avid reader. This is true, not a Penthouse letter. My cousin and I have flirted and joked about getting it on together for about 50 years or more. Now, she's divorced and having the time of her life. She told me the other day, what she'd really like is to have a "lesbian experience" with me watching and then joining. I'm so crazed with lust that I'm having a hard time thinking straight. This is a kinky dream come true. I love oral sex and with two pussies to eat, etc., the whole thing sounds just great. What I don't know is how to contact someone to do this. I don't want someone who's got a disease, or someone with a boyfriend just waiting to break in and rob everyone. Or someone truly horrific for any number of reasons. How do I contact, and then arrange such a thing? How would I ensure that my concerns are dealt with? Is using an escort services any guarantee of any degree of safety? Boy, I would just love some good advice. Got any for me? If you answer, you can call me... Old But Alive.

What's wrong with this picture? Just the gender of the letter writer, that's all. Turns out that my assumption that Cousin #1 (C#1) is female was wrong, wrong, wrong. C#1 is a man.

Dan knew that. I didn't. It never occurred to me that I had the gender wrong. He didn't realize that I didn't know.

So I sent my advice, which included:

1. "I hope you're indulging that lust with plenty of hot talk, make-out sessions, and role-playing as you figure out how to make your fantasy a reality." (Good advice.)
2. "Start hanging out at lesbian bars and other social venues. Don't go in aiming to pick someone up right off the bat—you don't want to come across as predatory and creepy. Instead, go on a date with your cousin, dance, chat up women who are friendly. You could make great connections if you're open and take your time." (Good advice if C#1 is a woman. Horrible, clueless, shudder-worthy advice since he's a man. No, no, no.)
3. "Another way to go, as you suggested, is to hire someone. The advantage of a paid escort is that you can choose the woman and spell out exactly what fantasy you want her to provide. She'll be experienced, creative, and totally focused on your pleasure." (The best advice of all.)

Dan sent me back a quick email that he disagreed with some of what I said, but he didn't tell me what. I was puzzled -- what could he possibly disagree with?

The column posted today -- you can read it here. To my shock, Dan broke into my lesbian bar advice with "About the only thing lesbians hate more than opposite-sex couples prowling for 'thirds' in their bars are sharp fingernails digging for clams in their pants." 

Huh? Where did he get the idea this was an "opposite-sex couple"?

Later in the post, talking about safer sex, Dan says, "Use condoms, Gramps." Who's he calling "Gramps," and where would these lesbians put the condoms (unless they're sharing sex toys)?

So it all comes out. C#1 is indeed a man*, and I've just gone from respected sex educator to clueless in the eyes of all the Dan Savage fans and Dan himself.

* (But Dan, don't call him "Gramps" anyway -- that's ageist and condescending. Whether or not he has grandchildren has nothing to do with his sex life.)

Once Dan and I realized what had happened, he apologized profusely, both to me for not clarifying the gender of C#1 and to his readers via a "Dear Readers" update. 

He told me later:

I thought it was obvious the letter writer was male -- his cousin wanted a lesbian experience, which he couldn't provide. That's why they needed a third and he would watch while the cousin had her lesbian experience, then join in. And he mentioned having two pussies to play with… not three.

So, that's the story, and now I can breathe more easily and sleep tonight. Now that I see it all in perspective, it's pretty funny that I jumped to the conclusion that the letter writer was female. I can laugh about it now. 

While I'm on the subject, finding a paid escort is less problematic than you’d think via the Internet or referrals – these women have found ways to advertise their availability, or they wouldn't be in business. Kendra Holliday, who describes herself as a sex worker from St Louis, tells me, “You can track down sex workers in your area online and run your scenario by them. If the sex worker is not into that kind of thing, she can float it by her network. Word-of-mouth is a powerful tool in the sex worker realm.” 

Thank you, Dan Savage, for all you do to create a sex-positive world! (See my review of Dan's book, American Savage, along with a gratuitous photo of his husband Terry in a swimsuit, here.) While you're at it, do subscribe to the paid version of his Savage Lovecast -- it's well worth the small subscription fee to get almost 1.5 hours of Dan every week.

62-year-old Woman Seeks Man for Sex

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Practically Sexless Marriage? Laurie Watson Advises

“Brad” wrote to me because he and his wife “Angie” are in a practically sexless marriage. I consulted AASECT-certified sex therapist Laurie Watson, author of Wanting Sex Again: How to Rediscover Your Desire and Heal a Sexless Marriage, to offer some advice. Obviously the couple’s problems are too complex to solve with one blog post, but I hope that Laurie Watson’s advice and, her book can help Brad and Angie take the first steps towards developing a sexually vibrant relationship.

Brad's Story

My wife Angie and I are in our fifties and been together since college. I've always loved her dearly. I've always found her to be desirable and let her know it. She is my best friend. Through almost all of that time, I've been dissatisfied the frequency and amount of passion in our sex life.

To say that the two of us have different sexual appetites is an understatement. Most of the time Angie says she simply isn't interested or too tired for sex. I, on the other hand, have offered and made myself available to her sexually. Despite being willing to attend to her needs, she has rarely reciprocated that willingness. 95% of my sexual release throughout my sexual history has come from masturbation.

I tell Angie that I love her, desire her, feel passionate about her, and I'd like to work on improving our sex life. She acknowledges that work needs to be done but usually says that now is not a good time, she's too tired, or she feels uncomfortable being sexual with the kids in the house. (Our two grown kids moved back to our small house for financial reasons.) When I ask how I could help resolve these issues or make suggestions for solutions, she generally discounts them or said she’s at a loss about what to do.

Things hit a further low point sexually about eight years ago. I was diagnosed and treated for prostate cancer (prostatectomy). I now have difficulty maintaining erections and too often there is an aching pain in the pubic region immediately after orgasm.

I’m unhappy about our lack of passion, intimacy, and sensual play (while acknowledging my shortcomings due to ED, low testosterone, and mild depression).  I’ve told Angie that I want to bring back more of the fun of sensuality and passion rather than concentrating on "the act." She continues to come up with the same excuses I've heard numerous times before.

A therapist years ago told us that Angie was depressed. She doesn’t get treatment for her depression, although she'll often self-medicate with marijuana. I think I’m depressed, too. We’ve always struggled financially. I lost my job during the recent recession and was out of work for over a year. I am now working full-time but my wages are substantially lower.

The last time we had sex together was a few months ago, at a hotel. I found it satisfying (any sexual contact is appreciated!) and she indicated that she found it satisfying, too.

 I want to turn things around, if it's not too late. I feel as if I'm running out of time. How do I go about improving the passion and sensuality between us? I've pretty much come to the conclusion that the only person I can work on is me. I cannot offer advice or solutions where it will not be wanted or accepted.

Laurie Watson replies:

In marriage, often one spouse is the pursuer, easily expressing needs, wishing for closeness, attention, and sex. The other spouse becomes a distancer, wishing for more space. Distancers often feel smothered by pursuers, who, in turn, feel starved by distancers. It can become a tug-of-war. Sexually, it can feel desperate. Examining the ways you have balanced closeness and distance might start to change things between you.

You both had an enjoyable sexual experience in a hotel, away from home, boomerang adult kids, bills, and the endless call of things to do. I congratulate you on finding a formula for great sex. As often as you can afford it, schedule a hotel rendezvous and indulge in relaxing, satisfying sex.

You’d like Angie to initiate sex and show that she desires you. Like many women, she may be more receptive, willing to be convinced, but not to initiate. Your wife may need your male energy and urgency to get her started.

Yet now more than ever, you need the reassurance that you are virile and desired after prostate cancer. How to do this without crowding the space between you and making her back up?

Try being a great seducer! The hotel adventure probably worked because you initiated a creative space for relaxation, intimacy, and sex. The chase and seduction are a good part of the turn-on. Often a woman’s craving for sex doesn’t kick in until about halfway through the experience. Then suddenly her aroused body says, “Yes, I do want sex!”

Men shouldn’t be responsible for all the work on the sexual relationship, though. Women can prompt themselves with fantasies, anticipation, and memories of exciting past love-making sessions, coming to bed mentally primed for arousal.

Prostate cancer brings its own set of challenges. Luckily, you still have desire and you still have some erectile ability. The sooner men start on penile rehabilitation post-surgery, the better their eventual outcome. Your deep pelvic pain, more common immediately post-surgery, absolutely necessitates a visit to the doctor to rule out infection, inflammation, kidney problems, and nerve damage. You may also need treatment from a physical therapist who specializes in pelvic pain.

Culturally, men are conditioned that they are good lovers if they have big, strong erections. But most women do not experience climax through penetration - only 15-20% ever do in intercourse. You can be a satisfying lover with manual and oral stimulation. With enough stimulation, men can reach orgasm with or without an erection - those are completely separate functions.

You have mentioned that your wife struggles with depression, as do you. It would be good if you both saw a therapist, seeking treatment for depression as well as your relationship issues. Even a single consultation would help a therapist see where you are stuck as a couple and guide you.

-- Laurie Watson, LMFT, LPC, AASECT Certified Sex Therapist, is the author of Wanting Sex Again – How to Rediscover Your Desire and Heal a Sexless Marriage. She blogs for Psychology Today Online in Married and Still Doing It. Laurie guest lectures at the medical schools for Duke and UNC Chapel Hill on sexual function/dysfunction. Director of Awakenings – Center for Intimacy and Sexuality in Raleigh, she maintains a full-time clinical practice.