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

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:

• Feeling alone? The best solution may be to travel... alone.
  
• The Best Advice EVER for People Who Fear Getting Lonely While Traveling Alone.
  
• 11 Unconventional Ways To Make New Friends As An Adult
• Elements of Wit: Mastering the Art of Being Interesting, by Benjamin Errett
• The Charisma Myth: How Anyone Can Master the Art (And Science) Of Personal Magnetism