SURVIVING THE JUNGLE OF LOVE: Dating Tips for Men Over 50
Discover the ultimate survival guide for men over 50 looking to dive back into dating. From essential grooming tips and dressing advice to avoiding common first date mistakes. Dating tips for Men Over 50
EDITOR’S PICKSRELATIONSHIPS
9/13/2024

Gentlemen, welcome back to the dating jungle—where the rules have changed, the prey is just as savvy as the hunters, and the landscape might feel a bit more treacherous than you remember. It’s been a while since you last prowled these grounds, but don’t sweat it. With a little strategy, some grooming TLC, and the right mindset, you’ll be navigating this wild terrain like a seasoned veteran. Ready to dive back in? Let’s get you prepared for the adventure ahead.
Alright, gents, let’s get one thing straight right from the start: the dating scene over 50 isn't just a pool—it's an ocean, and sometimes it feels like a stormy one. You might be rusty, feeling like a fish out of water, or more specifically, a fish that hasn’t flirted since the Clinton administration. But don't fret, just because you're navigating new waters doesn’t mean you’re destined to sink. With a little wit, wisdom, and a pinch of self-confidence, you’re more than capable of swimming with the best of them.
Time to Dust Off the Cobwebs - Grooming Tips for Men Over 50
First impressions are everything, and while the silver fox look is in, there’s a fine line between “distinguished” and “disheveled.” You’re a man of a certain age, and that means embracing your style with pride - and a good set of clippers. It’s time to book that appointment with your barber, trim the beard, and for the love of all things holy, tame those nose and ear hairs.
And let’s talk skincare. If your current regimen involves a bar of soap and a prayer, it’s time for an upgrade. A good moisturiser isn’t just for the ladies—it’s for anyone who wants to avoid looking like a well-worn leather wallet. Think of it as maintaining the chassis on a classic car: a little care goes a long way. And don’t skimp on the SPF. You’ve survived this long; let’s make sure your skin does, too.
Dressing the Part – Leave the Dad Jeans at Home
Let’s be real - nobody’s asking you to dress like you’re 25. (In fact, please don’t.) But ditching those dad jeans and that faded concert tee from 1985 will do wonders for your confidence. You’re over 50, not over the hill. Invest in a few key pieces that fit well and scream “I’ve still got it,” without trying too hard.
Think crisp button-down shirts, well-fitted jeans, and a sharp blazer. And don’t forget the shoes, women notice them, trust me. A polished pair of dress shoes or some stylish loafers can elevate your entire look. Confidence is the best accessory you can wear, but a nice watch doesn’t hurt either. Remember, you’re dressing for the part you’re playing: a mature, sophisticated man who knows exactly who he is.
Choosing the Perfect Date Venue – Choose Wisely, Young Grasshopper
Now that you’re looking sharp, it’s time to pick the perfect date spot. Skip the noisy sports bars (unless she’s a die-hard fan, in which case, carry on) and greasy diners. You want a venue where you can actually hear each other speak - think cozy cafés, quiet wine bars, or a restaurant with an ambiance that says, “I’m mature and sophisticated,” not “I’m cutting coupons.”
If you’re feeling adventurous, how about a cooking class, a museum, or even a stroll through a botanical garden? Just avoid anything that could result in physical injury—nothing kills romance faster than a pulled hamstring on the first date. The goal is to create an atmosphere that’s comfortable and intimate, without putting too much pressure on the situation.
Preparation – The Power of Planning
You wouldn’t walk into a business meeting without a game plan, so why would you treat a date any differently? Before you head out, think of a few conversation topics. What do you want her to know about you? More importantly, what do you want to learn about her? You’re not preparing for an interrogation, just ensuring the conversation flows smoothly.
Easy First Date Questions – Keep It Light, But Engaging
Conversation is an art, especially on a first date. You want to connect, but not come off as prying or, worse, boring. Here are a few questions that can get the conversation rolling without making things too personal too soon:
1. “What’s your favourite way to spend a weekend?” It’s a great way to learn about her hobbies without diving too deep.
2. “What’s the best meal you’ve ever had?” Food is a universal topic and can lead to fun discussions about restaurants, travel, or cooking.
3. “If you could live anywhere in the world, where would it be?” This is light and imaginative, helping you gauge her dreams and aspirations.
4. “What’s the most interesting place you’ve ever visited?” Travel stories are often full of adventure and shared experiences.
5. “What’s a book, movie, or show you’d recommend?” It’s a subtle way to find common ground in your tastes.
6. “What’s something you’ve always wanted to try but haven’t yet?” This can reveal more about her personality and future date ideas.
Remember, the key here is to listen - really listen and respond thoughtfully. Engage with her answers, share your own stories, and let the conversation flow naturally.
Talk About Yourself – But Not Too Much
Of course, she wants to know about you, but she doesn’t need your life story in one sitting. Focus on sharing your passions, hobbies, and what makes you tick. This is your chance to showcase your wit and wisdom—two qualities that only get better with age. You’ve got life experience, stories, and probably a joke or two that didn’t come from the internet.
When it comes to past relationships, honesty is key, but there’s no need to air all your dirty laundry. Acknowledge the past, but keep the focus on the present and future. And whatever you do, steer clear of ex-bashing—it’s a bad look on anyone.
What Women Notice First – Prioritise These, Gents
Understanding what women notice first can help you prioritise your efforts:
1. Confidence: Women notice confidence right away. It’s about carrying yourself with self-assurance, stand tall, make eye contact, and smile. Confidence is magnetic.
2. Grooming: Well groomed hair, a tidy beard, and clean clothes go a long way. A fresh, subtle scent doesn’t hurt either - just don’t overdo it.
3. Your Smile: A genuine smile signals warmth, approachability, and positivity. Plus, it’s contagious.
4. Your Style: Women notice how you dress, so make sure your outfit reflects the best version of yourself.
5. Body Language: Lean in slightly when she’s talking, nod to show you’re listening, and avoid crossing your arms - it can come off as defensive or disinterested.
6. Manners: Politeness never goes out of style. Open doors, pull out chairs, and most importantly, show respect. Good manners indicate that you’re considerate and thoughtful.
Avoiding First Date Pitfalls
Let’s talk about some common first-date pitfalls and how to dodge them like a pro:
- Oversharing: There’s a fine line between being open and being an open book. Keep some mystery alive - there’s always the next date.
- Trying Too Hard: Be yourself, not the person you think she wants you to be. If you’re not a foodie, don’t pretend to know the difference between Brie and Camembert. Authenticity is attractive, and it’s less exhausting.
- Being Too Negative: We all have our baggage, but a date isn’t a therapy session. Keep the conversation positive, and if you catch yourself complaining about your boss, your knees, or the weather, steer it back to happier topics.
You’ve Got This - Now Go Out There & Crush It
At the end of the day, dating over 50 isn’t about reinventing yourself; it’s about rediscovering who you are and sharing that with someone new. Sure, it’s been a while, but that just means you’ve got more stories to tell, more wisdom to share, and frankly, more to offer.
So, take a deep breath, adjust that new blazer, and step back into the wild with confidence. The water might be a little chilly at first, but with the right preparation and attitude, you’ll find it’s actually pretty refreshing. And who knows? You might just meet someone who makes you wonder why you didn’t jump back in sooner.
