A 50-something friend of my family lost his wife after a 30 year marriage and, about a year later, got back into the dating game. After about 3 months of trying to date, he described it to me as an inmate getting out of a long term prison sentence: complete and total culture shock. When he started dating his wife, Ronald Reagan was president, music was mainly played on cassette tapes, and most people still had black rotary phones.
In the present day, he had to confront realities of online dating, texting, dating across wide locales, and the fast-paced, cutthroat nature of relationships that all these options can bring. He couldn’t keep up and quickly got discouraged. His story is pretty common. However, there are also older guys who are extremely successful in dating. Later in the article, I’ll share a story that should make any older man feel good about his dating prospects (if you make the changes necessary to be a quality older guy).
By the way, I’m purposefully not defining “older.” But, for the purposes of this article, it can apply to people in their 40’s, 50’s, and beyond. Now, without further delay, here are my dating tips for older guys.
Embrace New Technology
For many older people, people found dates through family, friends, school, bars, or community events. They might have tried a few “outside the box” ideas like matchmakers, personal ads, or video dating (recording your information and sharing it with women). But, generally people had very few options and places to meet women outside of their family/friend circle.
While many of these methods are still viable options, the internet and smart phones have expanded a guy’s choices, both in terms of the sheer number of women he can meet, and the geographical range of these women. However, I’m amazed by older men who still resist internet dating, usually out of some stubborn traditionalism.
However, most people, even older people, are embracing technology. It might not be internet dating, but it still involves the use of texting and social media. At the very least, you should use those to your advantage. But, why stop there? Download online dating apps, get on MeetUp and find singles gatherings, use social media to find groups where you might like to meet new people, and so on.
Sure, technology can be a blessing and a curse. But, embrace the blessing side and you’ll find more dating success. If you don’t, you might even get left behind…like when that nice women you met “in the real world” at church insists on texting you.
If you are tempted to talk about the “good old days” of dating, you have a selective memory. Dating as a young, inexperienced guy is pretty brutal. The nerves, insecurity, and lack of knowledge can lead to awkward romantic moments or even being chronically single. Unless you were a young stud, your first few girlfriends probably don’t look back at you as a Don Juan.
But, now that you’re older, a few things should hopefully be true. First, you should have learned valuable relationship lessons. That should let you avoid a lot of headache and heartache. Second, let’s hope you have more confidence, in yourself and your abilities to attract, keep, and please a woman. Third, you’d better have your life together, financially and otherwise. I don’t want to be crass about attraction, but, yes, women do appreciate a guy with funds.
Most women, especially younger ones, are desperate for mature, stable men since they are often surrounded by immature boys. You should definitely play up your stability and maturity (to a point at least – see below). You might see “old and outdated” when you look in a mirror, but a women might see “stable, mature, confident man.”
If you’re older and still an immature boy, then get your shit together. Otherwise, you’ll stay old and single.
Don’t Look or Act Your Age
I know this sounds contradictory with my previous advice. But, bear with me. Many women crave a stable, secure man. But, they also crave a stable, secure, physically attractive guy who offers them excitement. If you can give them the first half of the equation, you’ll have a chance to succeed. If you give them both parts, you’ll absolutely be successful.
First, don’t look like an old man. Work out. Lift weights. Take off those last few pounds. Get stylish glasses and a stylish haircut. Wear clothes that look good, aren’t ten years old, and fit. Make women of all ages think, “wow, he’s a hot older guy,” not “he looks like a great-grandpa.”
Second, don’t act your age. Again, this isn’t contradictory. Certainly, act mature and responsible (not a boy). But, don’t act like an uptight old fogey either. Have fun, be open minded, try new things, and seek adventure. You might not have many years left so live life to the fullest. And, if you get accused of having a mid-life crisis, flip those jealous people the middle finger. Seriously, who cares what they think? We think a mid-life crisis is often a good thing.
However, I want to add that you want to look and act appropriately young. You don’t want to turn into a joke or a cartoon. This means not being overly trendy or faddish. A 50-something with a Justin Bieber haircut riding his skateboard at the mall looks stupid. However, a 50-something who looks 42 and is dressed in stylish clothing attending a local festival will look attractive.
Expand Your Horizons
You likely have an idea in your head of what dating should look like. You’ve set logical parameters of the kind of woman you should date. Well, take those images and shatter them! Set your ranges broadly and consider dating younger if that’s what you want. But, don’t rule out older either. Keep your options open, rather than closed. Definitely don’t let people shame you for your attraction preferences. You’re not required to date a certain type of person.
The story I referenced earlier is a friend of mine who married a 55 year old guy. She was 28 at the time. So, if you want to date someone younger, it’s very possible. And, you can find love at any age or with someone of any (legal) age.
But…dating is harsh. And, rule number 1 in dating is this: be attractive. The 55 year old guy in my story was in shape, dressed youthfully and is a popular DJ. My matchmaker friends tell of a 50-something guy who wanted to date 20-somethings like George Clooney. As my friends told him, “but, you’re not George Clooney.”
It was true. He was grossly obese, wore terrible clothing, and, was known for being an uptight, hothead. They let him in on a harsh reality. Just because you get in the dating market again and throw up a profile (or consult matchmakers) doesn’t mean that hot women (or any women) will be lined up to date you.
That’s why it’s important to follow the dating advice in this article. Check out our various articles, coaching packages, and products too. We can help you find love, even if you think it’s too late.