dating in your 50s as a man

Dating in your 50s as a man can be challenging. It may be a while since you dusted off your dress shoes and took a woman out on a date. As you might have noticed, the dating world has changed A LOT in the last few years. And it isn’t stopping anytime soon. So, as a man who is in his 50s or older, how do you date with confidence and find the right woman?

You may be wondering how to navigate dating apps and texting. On top of all this, you still face the same old dating struggles you faced when you were younger.

How do you find the right woman? And once you do, how do you connect with her in a way that creates a spark and makes her eager to see you again?

Not to worry! Today’s blog post covers smart tips for dating in your 50s as a man, even if you’re an introvert. After all, I’ve been an introvert confidence and dating coaching for the past eight years. All of my dating coaching clients are 35+ and many of them are in their 50s and 60s.

You may have seen my introvert dating and confidence advice in Forbes, CBC News and HuffPost. All that is to say that I know a thing or two about dating after 50. Read on to discover some of the insights I’ve gained from working with dozens of men just like you.

6 Tips for Dating in Your 50s as a Man

Set goals and intentions

The first step to get what you want is to know what you want. Think big picture. What do you want your dating/love life to look like one year from now? Ideally, would you be in a committed relationship? Heading towards marriage and family? Or playing the field?

There’s no right or wrong answer! Whatever you desire is fine, but it’s important that you’re honest with yourself (and the women you date) about what you really want.

If you’re not sure exactly what you want, scale things back and think about what you’d like your dating life to look like in the next three months. Chances are, you want to go on dates with great women and actually enjoy yourself.

As you go on dates, never leave the house without an intention. Have a purpose for the interaction that isn’t overtly self-serving. For example, you might set an intention to make her feel good, connect meaningfully or be fully present on  the date. This will help you to stop trying to impress her and start actually connecting.

Know your dealbreakers and must-haves

Knowing what you want in a woman is also key when you’re dating in your 50s as a man. Otherwise, it’s all too easy to waste precious time going on dates with the WRONG type of women.

You can save yourself a lot of energy and heartbreak by being clear on your dealbreakers and must-haves. In other words, what will you absolutely NOT tolerate in a partner? And what qualities MUST she possess for you to be with her?

If you’re unsure how to answer these questions, think about the stopping points in your past relationships. Maybe you’ve dated a lot of women who were dishonest and emotionally unstable. If that’s the case, be sure to put honesty and emotional stability on your must-haves list.

It’s also important to be real about your expectations. While there’s nothing wrong with wanting to date a younger woman with no children, that definitely narrows your options.

Consider the underlying reasons why you want a younger woman and be open to finding those qualities in a woman who’s a bit older than you expect (after all, JLO is one of the most vibrant, sexy woman on the planet and she’s in her 50s).

Know your assets

“Why would a woman be attracted to me?” Many men ask themselves this question in a self-defeating way. But it’s important for you to know the real answer to this question.

While dating in your 50s as a man, you might feel less desirable than younger men. Not true! Case-in-point: I have a gorgeous girlfriend in her early 30s who likes dating older men in their 50s and 60s. One day I asked her what she liked about older men and this is what she said:

“So many things! They’re present, they’re not on their phones all the time. They’re gentlemen, they have their shit together. They treat you like a queen, they’re great in bed and I feel like I can trust them more than men my age.”

Yes, you may be very different than men in their 20s and 30s, but that’s exactly why quality women will be attracted to you! They’re tired of dating little boys and want a mature, experienced man who will be more on their level.

So, go ahead and make a big abundant list of all the things women might find attractive about you. This can include character qualities, physical attributes and lifestyle.

Understand women

Do you feel like you understand women? Do you know what they like to talk about and how they convey their attraction? These are essential things to know as you re-enter the dating world.

The good thing is that even as dating continues to evolve, what women want remains the same. Women want to have their FEELINGS cherished in words and actions. This means picking up on emotions she shares in conversation and reflecting them back to her. “That sounds stressful, I can see why you’d feel angry!”

Women also fall for a man based on how he makes her feel about HERSELF. So, it’s useless to focus on trying to impress her. Instead, focus on making her feel good by being curious about her, complimenting her and conveying your attraction to her. Women are turned on when they feel desired.

Know where to meet women

It’s hard to meet women if you spend all your time either alone or with your male friends. The key to meeting great women is to go where they hangout.

Join Meetup groups and adult education and dance classes to meet women who share your interests. Choose weekly events/classes so that you’re meeting on a regular basis. After all, it’s hard to connect when you feel rushed and pressured to ask her out the first time you meet.

Update your style

Updating your look will help you get noticed by more women. It will also give you a confidence boost. If fashion has never been your strong suit, don’t worry!

You can enlist the help of a female friend or family member. Be sure to take a moment to consider what vibe you want to convey. For example, when I help my 1:1 dating coaching clients to update their style, I ask them if they’re going for a sporty, casual, elegant, classic or trendy look.

Next, do a Google search: “sporty men style”, “classic men style”, “older men style”.  Save the outfits you like and mimic their look. You can even bring the pictures to the store and show the salesperson.

Be sure to pay attention to accessories too. Watches, shoes, and belts make all the difference. Also notice the way the models wear the clothes. For example, they might roll their sleeves or pants in a certain way. Have fun with it!

More dating tips for introverted men

When it comes to dating in your 50s and beyond, knowing how to communicate and create a spark is key.  Remember, even if you’re normally quiet and reserved, you can confidently connect with attractive women.

I go into detail about all of the above in my Dating Masterclass for Introverted Men. Access it for free here.