The 6 BIGGEST Mistakes Men in Their 50s Make With Dating

10/3/2016

A recently-divorced, 59-year-old man recently asked, "I'm so lonely -- what should I do?"

While it sucks that he is now single and alone... the good news is that roughly 50% of marriages end in divorce these days, so there are plenty of beautiful, single women out there. Meeting them in real life can be hard -- but here's something most 50-somethings don't know:

With a little bit of effort, you can have incredible success with online dating!

Just don't make the same mistakes 80% of men your age are making, which is this:

Lots of men in their 50s get divorced and think their next girlfriend is going to be 35.

Get real. She's not. I mean, maybe... if you're, like, super rich. But realistically, no. Your next girlfriend isn't going to be 35.

But because so many guys think/want/expect that... that means there is a whole world of single, beautiful, successful women in their 40s and 50s who aren't getting a whole lot of dates online. If you’re willing to be realistic and date women who are an appropriate age for you, you might stop feeling lonely sooner than you think.

Now. If you want it to work out with one of these women, you've got to do more than just ask them out. You've got to avoid making the four big, dumb mistakes all the other dudes are making. These include:

1. Being bad at dating.

Look, I get it: you’re super new to dating. You’ve been married most of your adult life, and probably either are or feel rusty. That’s fine — the women you’ll be dating are new to dating, too. And so are the other men they’ve been out on dates with.

There are some very basic, easy ways to instantly be "better" at dating. First, put in the effort to dress yourself half decently for your date -- take shower first, and don’t show up in a graphic t-shirt you got for free at a trade show. Wear, like, a button-down. Don't wear gross old jeans with holes in them. Remember: she will almost certainly have spent some time on her hair, clothes and makeup. Show her the same respect.

Do this, and you will probably make a better first impression than the majority of men she’s been out with. (It’s a sadly low bar.)

2. Talking about your ex during the first date.

Maybe not the second one, either. Maybe not for a long time after you start dating. It’s fine to mention that you’ve been divorced for however long, and that you have n kids who ______. But you don’t need to go into any details -- especially bitter ones. That will leave a sour taste in her mouth and make her think you're not ready to date yet.

Remember: she’s your date, not your therapist. Focus on having a good time, asking great questions, and listening while she answers them.

3. Not paying for the date.

If you initiated the date, you should be the one who pays for it. It’s called manners. There’s a lot of weird misinformation out there about how feminist women will be “offended” if you offer to pay for the date. Because, first of all, they won't be. Second, on the off chance that they are offended by a kind and generous gesture, it's best to avoid them. Do you really want to be with someone who gets offended that easily?

That said, it's 2016, so anything could happen. She might insist she pay her own way, or even offer to pay for you. Whatever you're mutually comfortable with is fine.

But, really, if you are the one who asked her out, and you didn’t tell her ahead of time how much the date was going to cost (e.g., “The tickets are $23 — I’ll send you a link to the ticketing office”), then it’s a little weird of you not to at least offer to pay.

(But keep in mind: it’s also a little weird for her to act anything but grateful if she lets you pay. If she acts entitled to your time/money/resources, that's bad news.)

4. Not being authentic.

As I wrote in You May be Asking All the Right Questions, But Here’s What You’re Forgetting, increasing your charisma and authenticity will improve your personal and professional life. The thing is -- it can be super tricky to be authentic and charming when you've got first-date nerves.

Here are a few tips to get you started.

Stay present. If you’re constantly worried about the next thing you’re going to say, you’re not truly listening. Chances are, the next thing you say is going to be a bit of a non-sequitur. Plus, if you’re not listening, it totally shows on your face. I'll say it again: stop worrying about what you're going to say next. Staying present and truly listening will get you much further than some witty comment.

Acknowledge the elephant in the room. As I wrote in These Specific Behaviors Will Make You More Charismatic, Starting RIGHT Now, it only takes humans 17 milliseconds to notice and interpret an emotion on your face. But most of us misattribute what we see. See, we're humans. Humans are self-centered. We assume everything is about us. So if you're too hot in that jacket, I’m going to see the discomfort on your face – and think it’s about me. If you really have to pee but I’m in the middle of a sentence, I’m going to think you’re desperate to get away from me. If you keep looking over my shoulder because you’re afraid of missing the bus, I’m going to think I’m boring you. So just tell me! That way, I can correctly interpret what I’m seeing, instead of feeling like I make you uncomfortable and dodgy.

Hack your brain. Cognitive reframing is one of the most powerful psychological hacks in the whole world, and most people have no idea it exists. Basically, your brain is terrible at distinguishing fantasy from reality. If you imagine a completely made-up story, part of your brain will believe it’s true. So if you’re someone who gets anxious or distracted easily, take a minute to imagine that the person you’re about to talk to is a Nobel Prize winning scientist, a professional athlete, or the best ____ in the world. Part of your brain will cling to the memory, and you’ll focus more intently on the person you’re talking to. Likewise, if you get nervous easily, spend a moment imagining you already know the person super well – your moms were friends when they were pregnant, and you’ve known each other since you were babies. That will help you get over your nerves, and even treat this person with a surprising amount of warmth. That will make them like you more, which will make them like you more. It's a beautiful cycle.

5. Playing games.

Don't be a man-child. If you have a nice time on the date, tell her! When I go on a great date, the guy usually texts me before I even get home to let me know he had a wonderful time and can’t wait to see me again. If he doesn't -- if he waits a day or three days or whatever dumb “rule” he thinks he needs to follow… I don’t go out with him again. It means he’s obsessed with what others think of him — and, apparently, that he would rather I associate him with feelings of confusion and anxiety than excitement and joy.

That said, don’t overdo it. After an amazing date, message her once. If she doesn’t write back, don’t keep messaging her. Either she’s not a texter, or she wasn’t feeling it. (You can still message her in a week or so to ask her out again, but if she says no and doesn’t suggest something else, let her go.) You should message/call/contact each other in roughly equal measure. This is really hard for someone who is both lonely and excited about someone new.

6. Touching too soon.

Although plenty of women have exciting, fulfilling sex lives in their 40s and 50s... a super common complaint is that a man touched her weirdly on the first date.

Like, look. Maybe to you, "innocent" touch like holding hands or kissing are ways to show you're interested in someone. But lots of people find this kind of touch extremely intimate -- after all, the primary goal is to show emotion and affection, not to have an orgasm. Which is why so many women find it uncomfortable when some dude they don't even know starts holding their hand, touching their face, or trying to kiss them.

Of course, every woman is different. There is no algorithm you can memorize to tell you when to kiss her. There is no universal calendar of when to do different kinds of touch. Instead of relying on some bullshit you read on the internet, you need to pay attention and get your own read on the situation.

I'll repeat: there is no set of "rules" that will tell you when to kiss (or whatever) a woman. But there are some pretty clear signs that she doesn't want to kiss. As I wrote in How to Know Exactly When NOT To Kiss a Girl, it's okay to kiss a girl when:

You don't have to restrain her or surprise her to make the kiss happen. Remember: an unwanted kiss is disgusting. Consent is sexy. If you have to be quick, sneaky or forceful to get the kiss, you're doing it wrong, and the girl will definitely not be into it.

You ask if you may kiss her -- and she says yes. Some men mistakenly believe that "asking will kill the mood." Trust me -- if she wants to kiss you, it absolutely won't. She'll say yes! Unless maybe she wants to but she's just not quite ready yet. Then she'll say no -- this time. But! She'll feel super safe and respected with you, which will help solidify your bond.

She makes the first move. It's 2016. Plenty (but, admittedly, not all) of girls are willing to make the first move! And it's super sexy when they do. Just, you know. If she's had a lot to drink, you should ask yourself whether she's really able to give consent right now. Especially if you're hoping to have a long-term thing with her. Kissing her when she's drunk is going to mess up your chances of ever having trust.

You have a "moment." Refer back to Point 1. Mutual, consensual kisses are not "stolen." They are not fast, sudden or sneaky. Instead, they come after a moment. Perhaps you've been staring into each other's eyes -- then lips. Then eyes, then lips. Maybe she's touched the side of your hand with the side of her hand, and now you're holding hands. Parts of your bodies may be touching -- your arms, your legs. Maybe you've even pushed her hair off her face or brushed her cheek with your hand. Your bodies are gravitating towards each other...

But even then, there's room for misinterpretation. The only way to make sure the kiss is consensual is to:

Follow the 90-10 rule. AFTER you've had a moment, and you're feeling pretty certain this girl wants to kiss you, you can initiate the kiss. Go up to 90% of the way to her face... then stop. Wait a moment. If consent is important to you (which, if you're not a despicable person, it is), you will never go 100% of the way to her face. Let her go the last 10%. If she wants to kiss you, she will!

One last thought:

Before you get tied down, it might be worth checking a few items off your bucket list. You’re freer than you’ve been in a long time — and than you probably ever will be again. You’re also younger and healthier than you’ll ever be again. So book that flight! Take that lesson! Hunt that boar.

Do your thing -- and you just might meet the right woman along the way.

Want to know more? Check out:

37 Comments

chatten met vreemden link

10/26/2016 07:15:01 am

Chatting is one of the common web-based tool used to keep in touch with loved ones, as well as strangers.

tao of badass discount link

11/15/2016 10:39:42 am

Sometimes everyone is like a stranger ,and it is preferred that this is the norm,but what interest is hidden by the fear of rejection in wanting to make contact?

Dvae

9/5/2017 09:14:57 am

Well at the risk of sounding a little shallow I have find out that most women who hit their 60s pretty much give up on themselves I mean I don't want Cinderella but I would like a nice decent girl next door type she doesn't have to be attractive just nice but even that's hard to find. Sure I hear the old story it's what's inside the package not so much the wrapping but let's face it you want old wrinkly cellophane wrapping your package or a good old-fashioned just plain wrapper?

Eva Glasrud link

9/5/2017 12:40:21 pm

Who you date is up to you. I'm just saying, lots of guys use that strategy... then end up being single for several years while they try to find a younger woman who's interested in older men. They might still end up dating younger, but it ends up being a 60-year-old with a 50-year-old, instead of a 50-year-old with a 40-year-old.

Jonathan

12/15/2018 09:18:15 am

Why should we settle for women that refuse to take care of themselves? It's better to be lonely than to settle for anything. Dont you think?

Sarah

10/8/2018 02:53:56 am

I've been on three dates the past month. All three men showed up in wrinkled shirts, dirty tennis shoes, and two to three days growth of whiskers. This is the over 50 crowd. What's with these men? They are old enough to know better. Guess they didn't have their wives there to tell them how to dress. So dang sad. Men if you want a girlfriend or companion at least try and impress her on the first date. There is alot of competition out there so get with it.

Laura

11/8/2018 09:41:37 pm

I dated a 69 year old widower who thought nothing of passing gas - loudly - on a date. Gross! I guess because we were older, and both lost our spouses that he felt like I was the replacement wife.

Elle

11/26/2018 05:05:16 am

So true! I guess this is where we truly must look beyond the superficial to the substance of these men. Somewhere, though, a line is crossed: passing gas, loudly, where the residual stench would skin a cat, and not apologizing? That's tough ... I mean, he's still trying to impress you, one would imagine; what will he do down the road, when he thinks he's got you? Yikes!!

Maer

11/4/2017 08:54:07 am

I'm surprised by the number of 70+ yr old men that contact me on dating sites. I am 59. Some of the comments I receive are shocking. Like, 'nice rack'. Really!? A clear way to alienate me. You are right on about the touching. I went to the ladies room on a date. He was waiting for me outside in the hall, pushed me against the wall and stuck his tongue down my throat. Horrific! I felt violated. Still hoping to meet a month weirdo.

Drew Arroyo

9/7/2018 09:56:01 am

"Wear, like, a button down."

Poor grammar while.simultaneously suggesting dressing well.

Strange.

9/10/2018 03:01:24 pm

Honey, it's a blog post, not a scholarly article. I'm allowed to be colloquial.

But if we're going to be nitpicky, what you didn't like wasn't my grammar. It was that I used slang. Those are two different things. :)

For more fun reading, since you love language, might I suggest:

http://www.thehappytalent.com/blog/not-to-nitpick-but-try-takes-the-infinitive-or-a-gerund-not-a-conjunction

http://www.thehappytalent.com/blog/its-not-rediculous-its-ridiculous-heres-why

http://www.thehappytalent.com/blog/if-youre-not-a-psychologist-positive-reinforcement-probably-means-the-opposite-of-what-you-think-it-does

http://www.thehappytalent.com/blog/why-i-absolutely-hate-the-word-vagina

http://www.thehappytalent.com/blog/its-not-prejudice-its-prejudiced-heres-why

And, of course:

http://www.thehappytalent.com/blog/forget-moist-unpack-is-the-most-terrible-cringe-worthy-word-of-all-time

Marie

10/8/2018 07:13:38 pm

Lol! Bet that message was communicated. I am 66 yrs old enjoying these blogs. Be nice of someone couples up through this blog even.

10/8/2018 07:20:21 pm

Drew! It's an open blog. Nice to hear it from a guy the dress preference for a date. How about lightening up on those expressing themselves in their essence. Relax, have fun

David link

1/22/2019 01:46:11 pm

After 34 years of marriage, my wife told me that my wearing wingtips on our first date was almost a deal killer. Still peeling back the layers of the onion. Fortunately she was already smitten.

Bradley Keller

10/2/2018 01:23:21 pm

Well these are all generally true for the US culture. One must always remember that everyone is different. IE I recently had a 57 year old male friend marry a good looking 24 year old native Califorian born female and he is not rich, conformable yes. She just wanted a stable serious male that wanted children. Two years and two babies later they are very happy together. The way to do this more redally is to visit cultures where big age diffences are more common and culturally accepted like Columbia or the Philapeans.

10/4/2018 10:19:47 am

Definitely true. I was in the Philippines this year, and they had very different attitudes about large age gaps in dating. It's good advice, and I definitely met a few men who were there looking for a wife.

Troy

10/5/2018 04:57:34 pm

Yeah my next girlfriend wasn't 35, she is 23. I'm happy being 50.!

Adriana

10/28/2018 01:25:21 pm

Let’s see for how long your 50 year old body will manage to keep up with another generation lol

S--

10/8/2018 04:01:59 pm

Funny thing is, it's written by a woman who actually thinks this is exclusive to men. Lol. Is the brat also attempting to reenforce the myth of the older man usually desiring the much younger, beautiful woman, who in turn usually desires the much older, richer man? Well then I don't think she is aware of "vice versa", which very easily applies here. Or is she? Lol.

10/10/2018 10:40:13 am

I'm not sure I quite understand your argument, but I'd like to. Could you clarify?

I'm also not pretending this is exclusive to one gender or the other. I'm just sharing my experience as a matchmaker who worked mostly with single women, and therefore knows some of the main criticisms single women had after first dates.

Annette L Washington

11/16/2018 09:46:15 pm

Thank you. It's a shame that people can't appreciate your intent. Thank you for writing this and sharing it to help and guide people.

Avi

10/9/2018 01:47:24 pm

This is completely wrong. This was clearly written by a woman trying to change men to make them better for her tastes, pretending to be an article designed to help men get what they want. This is only going to confuse men and frustrate more women. Lying and manipulation don't work to build relationships or anything real. Sorry Charlie.

10/10/2018 10:42:21 am

"This" doesn't mean anything at all. If you have a specific criticism, I'd love to hear it, though. More viewpoints is always better.

Paul

8/5/2019 03:22:22 pm

There are very few gentlemen left in this world..if you're a man on here getting offended by what the lady is saying .. you're some kind of idiot!!

A conforti

12/8/2018 02:45:46 am

Really? You must be one of the rumpled, fat, bad mannered jerks I've met over the last 5 yrs. Men, iron a collar or take it to dry cleaner to be pressed. Get a haircut. Think back to manners your momma taught you. And please remember you might be out to get paid, but we are not. We are looking for a relationship. Many of us have given up on dating because you have no manners and are rude and disrespectful. Better to be alone. I think the point was to give you tips to help you. Cannot help those who don't want help but men in this age bracket seriously need it.

Heather Estes

12/19/2018 02:01:31 pm

I agree that it's better off for you to be alone...lol.

Shirley

10/25/2018 05:55:54 am

Just how does a woman feel when your having a conversation and he takes it out of context and makes it sexual. Especially when you've never talked or met them, only texting.

Richard

11/1/2018 11:26:43 pm

I actually got a lot from this. It makes sense. As a guy I do want that love, trust, affection and partnership. But I also have sexual drive which has to be kept in check in those first few dates. Its a pretty powerful driver and as much as we want to connect with some feelings, guys could quite easily have sex on the first date and maintain growing connectivity. So this advice is good advice. Keep your hands to yourself boys and keep willy in the pants. The girl wants to grow emotionally first - respect that. But I'm, still looking for that beautiful person - sadly.

-Linda

11/15/2018 11:59:16 am

I look a lot like Barbie (the doll). I'm in my 50's. Dating a man 2 years younger. He's a large man, easily two of me. I understand and accept that he likes me for my looks and he understands that I like him for his personality.
By the second date we both wanted to have sex but "we" (he) chose to wait. Third date was an awkward but fun experience.
Now, two months in, much to my surprise and delight! he is by far one of the best lovers I have ever had.

My advice to men and women: Get your game on and bring it! Be the person you want to be with. Smile, flirt, get close but always let the lady set the pace.

Luko link

11/9/2018 09:00:17 am

Men, of all ages, be mgtow and live life HAPPY

Nancy

11/26/2018 09:46:45 am

Typical article, not bad. Especially, not as horrendous as the ones written for dating in your 20’s. I’m 48 now and dated a man in his mid 50’s for 5 years. He is the greatest love of my life and treated me the way a woman should be treated. He wasn’t creepy or smarmy. He was and always will be a strong, sexy and confident man. Not sure if it’s his Italian upbringing or what but man, he could run circles around a 25 yr old any day. Sadly it ended but I’ll always be grateful for the times we had and the memories we made.

11/27/2018 11:52:38 am

Nancy,
Why did it end? I'm dating a strong, confident man right now and would like your insight.
Thanks.

Julie

12/18/2018 01:16:19 am

Great article! It really helped me realize that I still have a chance at dating at 53. Thank you!

Carol

3/26/2019 08:34:41 am

I'm 43 and I have fallen for a 53yr old widower. He is amazing. I'm not sure if he is as interested as he claims to be though. His wife passed away, less than 2 years ago. He says that he wants to see me and see where this goes, but I have had no communication from him in a couple of days. Before we met, he would text me a couple of times a day but ever since we met, this has more than halved. I want to protect myself. I can see the potential with him and us. I am the first woman he has dated in 26 years.

Mike Johnson

8/17/2019 04:39:38 pm

I'm a 59 year old man.
I've been on online dating sites for about a decade, but only been on a few dates.
The women in their 50's I've reached out to have not written back, and the women who have reached out to me I have not found attractive.
So I feel stuck.
I've no problem with the author's recommendation to dress well- I wear well-fitting dress shirts and am relatively fit due to working out.
But, I am not handsome.
I've read that women care more about behavior than looks, unlike men. But, my lack of results in online dating make me skeptical.
I want a woman who will accept me as I am, but also one of average looks I would want to have sex with.
My friend's wives are mostly not attractive.
So perhaps pornography is for sex and a relationship is for companionship? Sad if so!

Dad

2/6/2021 04:11:12 pm

Stumbled on this hundred year old post and needed to help guys out.

I’m a short, 49-year-old man who makes an average wage in an unglamorous job. All of my friends live somewhere else in the world now and my kids are with me more than with their mother.

My last short-term relationship was with a 29-year-old woman. I made her laugh so much and teased her enough physically that she out of nowhere sent me a risqué photo. We dated.

So, no, you don’t have to be rich to attract younger women. And young women tend to have more agency over dating than older women—meaning they know what they want and have almost never been turned down. That girl and I didn’t work out because I! Got lazy and didn’t put in the work to keep it going. We still talk despite her dating another guy now.

The trouble isn’t old men chasing younger women—young women do a lot of the chasing of older men—it’s that women over 40 tend to price themselves right out of the market. They may have relaxed a physical standard or two, but that’s because they, themselves can’t command the level of attractive men they really want. So they up their other checkboxes, like their lucrative career, owning a home and world travel somehow entitles them to access to high tier men. Nothing could be further from the truth.

Most men are attracted to femininity. Femininity in non-Asian or non-Hispanic women over 40 is just gone. It’s like dating someone’s grandfather. I might as well move a male roommate in.

So if you guys want to attract women, get the hell off the online dating apps unless you’re a model and go to any place where you would be around the same women again and again over time and talk to them like you’ve known them 20 years. At some point one or more will give you indicators of interest. Might not be day 2 or week 2. But at some point, just like school, being familiar to women enough for them to see who you are will bring one or two a little closer and give you your shot. Take it.

joe swanson

3/18/2022 04:46:19 pm

Make sure your dick works. Get a hooker if you need to practice. Older women love and want sex all the time. Not like it when they were younger and protecting themselves. A limp dick will not get you too far in a relationship.

The 6 BIGGEST Mistakes Men in Their 50s Make With Dating

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