The Ultimate Guide to Sex after Fifty

I am seventy-eight and have been widowed for ten years. Going on the dating sites took courage and a sense of adventure. I met some liberating and interesting men. Two were over sixty and became wonderful lovers. I used to feel that sex was only right within marriage. Wrong—at this age and stage, no need. I still have much to offer. There is still fire in the furnace.

You’re ready to connect for dating, sex, love, companion-ship—but dating at our age feels awkward and downright weird. What are the guidelines? How do we meet someone? How do we navigate the jungle of online dating and avoid the tigers, snakes, and jackals? Welcome to the club! Whether you’re widowed, divorced, a breakup survivor, or a longtime single, figuring out how single seniors meet and mate—or try to—may seem like a deep mystery.

•Single women seeking single men: there are only seven men for every ten women age sixty-five or above.⁹³

•Forty percent of women and 13 percent of men over sixty-five are widowed and single.⁹⁴

•Thirteen percent of women and 12 percent of men over sixty-five are divorced, separated, or for another reason living without their living spouse.⁹⁵

•Five percent of women and 4 percent of men over sixty-five are single and never married.⁹⁶

Note: I’m frustrated that the federal agencies and academic publications seem to track only traditional, legal marriages, with no mention of LGBT long-term partners in states without marriage equality, or alternative relationships. I hope that this changes.

As much as I would like to share my life with a significant other, I love my life the way it is and I’d rather not be in a relationship, than be in a relationship with the wrong person.

It’s tough to be single after fifty or sixty. As a straight woman, I’ve felt invisible. Men my age and older seem to want younger women, way younger. When I tried to make the point on a dating site message board about the splendid qualities and joie de vivre of women our age, questioning why men wanted to date women more than fifteen years younger, men scoffed and talked about the “scenery.” Hey, there’s nothing wrong with our scenery, guys.

I give a dating workshop called “How the Heck Do We Date at This Age?” We all seem distressed at the craziness of trying to mix and mingle as older people. For many of our generation, the last time we were single was in our youth, when everything was different—the times, the social structure, and yikes, we were different. Opportunities were everywhere; practically everyone we met in our social circles was also single, and a good many were interested, thanks to our youthful hormones.

Maybe finding love wasn’t easy (when has that ever been easy?) but dating and getting to take off our clothes together didn’t take too much ingenuity, if that’s what we wanted. Believe me, I’d never return to those times filled with restrictive mores (remember sitting by the phone waiting?), unrealistic expectations (a mate would complete your life and you’d skip into the sunset together?), and the constant fear of discovery and pregnancy. Sure, it was simpler—we all knew the rules. We either followed them or broke them, but we knew them. But now…?

If there are new rules of dating, no one knows what they are. So let’s make up our own. Here are some of mine—which ones resonate with you?

1. If I want to attend a social event, I go. I don’t need a date or a posse of friends. I arrive when I want, leave when I want.

2. I approach people I’d like to know. I start conversations, ask questions, once in a while end up with an exchange of email addresses or phone numbers.

3. I use online dating and feel free to send the first message.

4. I tell the truth about my age. I know that eliminates some potential dates who want to meet younger women, but what’s the point of getting someone to meet me when I’m not what he’s looking for? Duh.

5. I don’t prolong the pain if I can see that we’re not a match. I say no politely but clearly.

I recommend making a list of the qualities you’re seeking. If you don’t know what you’re looking for, you either won’t find it, or you won’t recognize it when you do find it. Try this:

1. Make a list of thirty qualities that you’d like to find in the next person you date. (This is not as big a job as it sounds—just don’t censor yourself. If you don’t come up with thirty, you can stop at twenty.)

2. Sort those qualities into three columns:

• Essentials are those qualities that are absolute must-haves to make you happy.

• Would be really nice adds those qualities that you could do without if everything else is great, but they would add even greater appeal.

• As long as I’m asking gives bonus points to some preferences that might be whimsical, but would add a delicious flavor.

ESSENTIALS, NON-NEGOTIABLE	WOULD BE REALLY NICE	AS LONG AS I’M ASKING

3. Let the first column be a mental checklist to avoid bothering to date people who are clearly wrong for you. Let your list guide you toward the potential partners who will be right for you.

I developed this system by accident. I was cleaning out my old collection of journals after I met Robert. I found one that I wrote in my late forties, pre-Internet days, bemoaning that I wasn’t meeting the kind of man I was looking for. I had made a list, which got so big that I divided it into the columns I described. In reading over this list decades later, I discovered that Robert had every last one of those thirty qualities—even those in column three. (Read Better Than I Ever Expected: Straight Talk about Sex After Sixty for our whole love story.)

Now, dating again (or trying to), I’ve revised this list several times. Is it time for you to make yours?

I’m a proponent of getting out and doing the activities you enjoy. If you meet someone, you already have that interest in common. If you don’t meet someone, you still have a good time. I met Robert when he walked into the line dance class I was teaching. Without our love of dance, we never would have met. He had no interest in online dating—in fact, he didn’t think he was looking for love at all. Falling in love blindsided us.

My situation is rare, though. Unless you live in a big city or a retirement community, the chances of meeting compatible, age-appropriate singles is low. So where are all those compatible, age-appropriate singles? Most are taking their chances with online dating.

There are sites specifically for seniors, but you don’t have to restrict yourself to those. All the major dating sites have plenty of people our age, and most hopeful singles list themselves on several sites. When you put in your age and the age range you seek, you’ll see them. Lots of them. I recommend online dating for our age group because that is where the people are.

1. Generic rather than specific. If it sounds like all the others, it won’t get read. What’s special about you? Put forth your best qualities and most important interests. Don’t waste your time with words like “honest, caring,” and so on. Everyone says that, whether they are or not. And skip “walks on the beach”—if all the singles who say that’s their favorite thing actually did it, the beaches would be jam-packed, especially in moonlight.

2. Blah blah blah rather than enlightening. Don’t just throw down words that don’t get us any closer to knowing you. This is your job interview! Unless your photo shows you as a Robert Redford or Sophia Loren double, you need words that attract us as well. If you sound like you don’t care and you’re just doing this as a lark, we won’t care either.

3. No special qualities. Ask an honest pal who knows you well, “What are my best qualities? What do I offer? How do I come across?” You may be surprised that you have qualities that you didn’t think to mention.

4. Badly written. If you’re not confident about your writing skills, ask a friend to help you. Don’t have the friend write it for you, and don’t hire someone to crank it out for you—it needs to be you. Proofread carefully. If you let spelling, grammar, and punctuation errors through, you give the impression you’re uneducated and you don’t care.

5. Negative. You can finesse how you say what you don’t want without seeming unfriendly, unapproachable, and angry. Spend time making your profile sound welcoming to the right people, rather than trying to scare off or stomp out the wrong ones. Again, a friend can give you valuable feedback.

6. Easy to skip. Remember that list you made of the qualities of the person you seek? Now imagine that this person is skimming profiles, one after another. How will the person you’re looking for know that you’re someone worthy of reaching out to? Work at presenting yourself so that the person you seek will be drawn to you in return. (Just please never post a “10 Requirements to Date Me” list—that’s a terrible turnoff. Subtlety reigns.)

I’m sixty-four and been single since age fifty-three. I learned the hard way that it’s best to be candid about who I am. I’m better off—and so are the men that I meet—if I’m a WYSIWYG (what you see is what you get) woman. There won’t be getting-to-know-you surprises.

1.Use a current image that emphasizes your best attributes as your default photo. This should be a recently taken close-up of your face wearing a friendly smile. Do. Not. Wear. Sunglasses. I can’t tell you how many profiles I skip over because the man is wearing sunglasses. I need to see your eyes. I also skip those that look unfriendly, so smile!

2.Make your default photo just you—no buddies on a fishing trip, no grandchildren, no pets, no arms around another person who might be your ex, and absolutely no edited photo with the person at your side cropped out. We can tell!

3.Have someone else take your photo. Our phones make it easy to take “selfies”—photos of ourselves, which are easy to spot. We never look good in them, and we’re usually scowling because we can’t see the little screen without our reading glasses. You don’t need to go to a photography studio—just ask a friend.

4.Include secondary photos that show you in some activity that you enjoy: hiking, playing music, creating art. Older photos are fine here, too—it’s fun to see the long, bushy hair and patchwork jeans that you wore in 1970—but label them with the year, and make those secondary photos, not your main one.

5.Include a secondary, recent photo that shows your build as well as your face. Yep.

QUESTIONS YOU ASK ABOUT DATING

Is it okay to lie about my age? If I don’t, no one will date me.

No. What’s the point? If dating prospects don’t want to date a person of your age, that’s their loss. Starting with a lie compromises your honesty and authenticity. It will come out eventually, and then how will your date know when to believe you? Let’s all agree to tell the truth, and create the world we want to live in, where aging isn’t a bad word.

Why do women show photos of their pets and grandchildren on their profiles? I don’t want to date their pets or grandchildren.

This is the most common complaint that I hear about women’s profiles. One man told me, “It gives the message that there isn’t room for me in her life.” Women: take note!

Why do men wear sunglasses in their profile photos? It looks like they’re shifty and hiding.

Either they’re shifty and hiding, or they don’t know that this bothers us. Men: take note!

Is there a nice way to ask women to send a full-body photo? Not nude or revealing, just showing their body type.

No, if she has chosen to post only head-shots, you can’t ask for a full-body photo without sounding creepy. (If it’s important that she be a certain body type, are you that body type, too? Do your photos show it?)

Why do men think that fifty pounds overweight is average build?

I wish I knew.

(From a man seeking women:) I posted my profile and got so many responses that I can’t possibly answer them all. What to do?

If you’re getting many responses from people who don’t fit what you’re seeking, make your profile more specific about what you’re seeking. If that’s not the problem, it’s probably the odds. There are many more women looking for men than vice versa. Try to answer those who write to you, even if you just send a quick, “You sound like a wonderful person, but I don’t see us as a match.”

(From a woman seeking men:) I posted my profile—why didn’t I get any responses?

See the previous question. Since men are in disproportionately in demand, many feel that they can just sit back and answer responses, rather than put out the effort to read through dozens or hundreds of profiles and make the first move. Go ahead and approach men who interest you—don’t wait for them to find you.

When I’m ready to have sex with a new person, how do I know if he or she is “safe”?

You don’t. Use barrier protection with everyone, every time. (Please read chapter 16, Safer Sex: Always.)

At sixty-five, I’ve been divorced for a few years now. Finding women my own age with whom I have a good mental connection has, surprisingly, been very elusive. I can’t tell you how many times I hear, “My cat (dog, horse, or other companion animal) is my best friend,” and “My life centers around my grandchildren.” I ask, “What are you passionate about beyond pets and family?” I seldom get any substantive reply.

Rejection will happen. You’ll reject many; many will reject you. It’s not a reflection of your personal worth, it’s just part of the dating game. It’s so easy to make contact via online dating, that you have to accept that the answer is often no.

If someone messages you and you’re not interested, don’t lie. Do be polite. Do answer, unless the initial message is inappropriate or creepy.

Make your No, thank you clear and polite—something like, “Thank you for writing, and I enjoyed reading your profile… [Insert something complimentary about the person’s qualities and/or interests here.] However, I don’t think we’re a match. [No need to give reason.] Best wishes for finding what you seek.”

Do not, please, lead someone on by email or phone, and then use responses like these to weasel out when your potential date presses you to meet in person:

I’m quicker than many to suggest a meeting early in the message/email/phone call progression rather than dragging it out. You can exchange information before meeting and get an idea of who the person is, but you can’t tell how you’ll interact or whether the chemistry will be there. That takes an in-person meeting: a first date.

If you think of a first date as your way to learn about another person and about yourself without risking anything, it can be fun. Go for coffee or a walk, talk, see what you both enjoy discussing and doing, see how comfortable you feel together. Easy, breezy.

It’s when you think of dating as interviewing a potential soul mate that it becomes fraught with anxiety, unpleasantness, and emotional danger. Tell yourself this: “I’m not auditioning someone for the rest of my life. I’m only auditioning for a second date.” Seeing it that way may help you relax.

First dates aren’t scary to me. I’m interested in learning what we do and don’t have in common, and which of the divergences matter a lot. Plus, the writer in me loves hearing people’s stories, and first dates are a great way to learn a huge amount in an hour, because it’s expected that we share our stories. Here’s what a first date is for me:

1. I get to know another human being whom I would not have met any other way. I listen a lot, ask questions, and try to learn about the other person.

2. I get to practice dating. How do I want to present myself? How much do I want to share?

3. I get to practice conversational skills. How can I do my part to create a satisfying give-and-take in our conversation?

4. I learn about myself as well as the other person. If I don’t want further contact, why not? How can I use this experience to refine what I’m looking for, and how I’m looking for it?

Be yourself, be truthful, tell your date about yourself—and ask pertinent questions to encourage your date to do the same. Take the opportunity to show your date who you are and what matters to you.

Don’t try to guess what your date wants to hear and enact that persona. We’re too old to play the I’ll-try-to-appear-to-be-who-you-want-me-to-be game. If someone would reject you knowing your political views, or number of divorces, or chronological age, get that over with early. Why waste everyone’s time when it’s clearly not going to work out?

Avoid talking in a nonstop monologue. Many of us chatter away out of nervousness and discomfort. You can’t learn anything if you won’t stop talking. I’ve had dates (first dates only) with men who talked on and on without ever asking me a question about myself. It made me feel that they didn’t really care who I was. Your job isn’t to avoid silences—it’s to learn enough about the person in front of you to decide if you want a second date.

I’ve been known to interrupt a long monologue, try to wind it down with some compassionate statement, and then ask, “Is there anything you want to know about me?” That usually kickstarts a dialogue, but sometimes it just gets more painful. Sometimes you can’t save a date.

I am fifty-three, and have found three romantic relationships and numerous casual female friends through online dating sites. The most important word is patience. For every one of my romantic relationships, I met twenty to thirty other women for coffee. Was I disappointed or frustrated that most of these meetings did not set off a ping of potential romantic spark? Not in the least! We had pleasant, stimulating conversations. They were almost all interesting women who could be nice friends (and several of them now are).

Don’t waste too much time texting, chatting, or emailing before meeting face-to-face. I have found that you easily create inaccurate, overly idealized versions of that person if you spend too much time corresponding before meeting. Meet as many people as you have time for an hour at a local coffee shop to chat, get to know each other, and see if anything clicks. Do not expect chemistry in 95 percent of the meetings, just good conversation.

I am now madly in love with a woman I met six months ago on OkCupid. Our coffee meet set my romantic ping on overdrive, and it ended with a kiss that could flatten several small villages. Be persistent, and eventually the chemistry will be there. Enjoy the quest as much as the treasure at the end!

STAYING SAFE

You’ll read some of this advice in any dating book, article, blog, or site. I’d be remiss if I left it out, though, in case you think it doesn’t relate to our age group:

• Beware of strangers from afar who insist they’re in love with you and want to visit you, but need a temporary loan. Disreputable people approach lonely seniors, seduce them with flowery language, fake photos, and assertions of love—and have a well-honed plan to rip them off. Any request for money is a red flag, whatever reason they claim. This is a crass and horrid business.

• Always have a few emails and phone calls before agreeing to meet in person. I recommend a video call such as Skype or FaceTime. The visual quality may not be stellar, but it’s better than nothing, and you get to interact. There’s a lot you can tell from people’s speaking style, the energy they put out, and your dialogue with them.

• Know the real identity of the person before you agree to meet. This may seem obvious, but don’t skip this step. Anyone can appear to be anyone online. (Have you ever watched the television program Catfish?) If a potential date won’t give you a full name (which you can Google), a personal email address, and a phone number, be wary.

• Meet in a public place: a coffee shop, park, or event that you’d both enjoy. Have a definite beginning and ending time so that you don’t have to worry how to end the date. I like to schedule first dates in a park where I love to walk—if the date goes sour, at least I got an hour of exercise.

• Avoid expensive first dates—no one should have to invest heavily in a first meeting. Assume you’ll be sharing the cost. Women: Throw out that old rule that the man always pays. If he says, “I want to treat you,” that’s fine, but don’t assume that’s the way the world works these days.

• If your date seems interested in your finances, close down the conversation.

• If your date seems creepy, gets too close, or makes you nervous, trust your instincts and end the date early. As much as I promote honesty, I’ll give you a pass if you need to say simply, “I don’t feel well. I need to leave.” That’s close enough to the truth.

• If you know at the end of the date that you’d like to see the person again, it’s fine to say something like, “I’ve really enjoyed this. I’d like to know you better.” But if the response isn’t as enthusiastic, don’t press. “Let’s email and decide whether to meet again” is respectful and gives your date an out who isn’t as eager to repeat the meeting. You’re both juggling other first dates and potential dates—never assume that you’re the only person in this stranger’s life—and your date might need some time to decide which people to follow up on.

Being older, you likely have medical issues. How much do you reveal, and how soon? See if you’re getting along and seem interested in seeing each other again first. If you can tell this will be the only date, you don’t need to go deep. But if you like the person and you’re enthusiastic about a second date, be honest about important issues that might impact the other person’s choice of whether to go out with you again.

Don’t dump endless details of your last health exam or therapy session, but do disclose up front what you fear will scare off a date—it’s better to know now. If there’s a health issue that would impact someone in a relationship with you, it’s best to reveal it.

Charlie Nox is a sex blogger and dating coach who is a cancer survivor. She gave a talk about dating with cancer at a conference I attended. “Don’t put cancer in your online profile—you’ll get ‘cancer spam,’” she advises. “Do tell on the first date.” Be aware that the other person will be uncomfortable and not know how to respond at first. Let your own speaking style show the attitude you want to hear back. (“Yeah, cancer is a shit sandwich,” Nox says to dates.)

If your health issue is sexual—erectile difficulties, vaginal pain—a first date is probably too soon, unless you sense a strong attraction and feel that you’re likely to get naked quickly, or you’re both at ease talking about sexuality. Otherwise, a good rule of timing is to keep sexual revelations until after the first passionate kiss or roaming hands. (You’ll need to take a break and talk about safer sex anyway, right?)

Practice ahead of time so you know how much or how little you want to reveal, and what conversational style you want to use when disclosing your situation. Encourage your date to ask questions, and be prepared to answer them straightforwardly, without embarrassment. If your medical condition makes your date run for the hills, that person would not be right for you anyway.

What determines whether there’s chemistry for us as seniors? During childbearing years it serves a reproductive purpose—our biology is matching us with some people and not with others for the good of the species. But if we’re not looking for a mate to propagate the species but for other reasons entirely, why isn’t it easier to find that elusive chemistry?

There are a lot of people out there, and there’s no reason to settle if imagining our date naked doesn’t turn us on. We’re not driven by our hormones these days, but we still want the person who ends up in our bed to make us feel delighted to be there.

That said, we all find different types attractive, and chemistry can grow as friendship and common interests develop. We may find ourselves attracted to someone because he or she is funny or smart or committed to the same causes we are, or fun on the dance floor, or easy to confide in.

If the attraction isn’t there, how important is that? Is sex and companionship with anyone better than with no one? That depends. Some enjoy a liaison for its own sake. Others are holding out for love and commitment. Most of us are somewhere in the middle, or it may depend on mood, circumstance, and how long it’s been since our last partner. Like everything else, it’s an individual choice.

The advice, then, must be to meet in person, give someone a chance, but if there’s nothing there, admit it, be kind about it, and move on. Some version of this works for me: “I’ve enjoyed meeting you, but I don’t feel the chemistry, I’m sorry. I don’t see us as a match.”

And if the chemistry is there and all goes well, how soon can you turn your date into a sexual encounter? Again, you make your own rules. Please read chapter 16, Safer Sex: Always, all the way through, and then read it again before going out on a date that you think might become sexual. Take responsibility for carrying condoms, dental dams, whatever you might need—don’t leave it in the other person’s hands. Be sure you’ve had the Condom Conversation long before any panting (or unpanting) begins. You are responsible for your own sexual health. Please don’t take chances.

I love this quote from sex columnist Dan Savage: “Every relationship fails—until one doesn’t.” It puts things in perspective. Most of your dates won’t result in anything—that’s just the way it is.

That doesn’t mean that the process isn’t working—actually, it is working. You’re learning more about what you want, and what you don’t, and how to screen for those. You’re practicing dating—honing your skills of getting to know someone, finessing how much to divulge and when and how, experimenting with how to present yourself.

These are valuable skills, and your education is costing no more than the price of a cup of coffee and an hour out of your week. Each lackluster or bad date brings you one person closer to the relationship that won’t fail. That’s no waste of time!

And if your date is truly awful, then you have a good story to share with your friends. (Tell me, too.)

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