40 Best Dating Tips for Men Over 40

On the market in your fifth decade? Don't worry! Just follow our helpful advice.

40 Best Dating Tips for Men Over 40

If you find yourself on the market in your 40s, you know how daunting it can feel. Long gone are the days of countless single friends, countless single bars, and endless time on your hands. And besides, you may feel a bit rusty—even nervous!—as you jump back into the game after a long absence. But listen up: Don’t worry, brother! Looking for love in your fifth decade isn’t nearly as difficult as you may imagine. Just follow these key pieces of dating advice for men over 40. And before you jump back in, remember that there are exactly 17 Things You Should Never Say to a Woman.

40 Essential Dating Tips for Men Over 40

Embrace the new world.

So you’ve been out of the game for a few years? Let me get you up to speed. Today, we’re all a lot more searchable and socially connected, so, just as you’d leave a “positive paper trail” for potential employers who Google you, you need to do the same for your love life. (Get on social media and make sure you’re projecting a healthy image into the world. She will be Googling.) And up your text game. You will find yourself doing more texting than you’ve ever imagined. And for more great tips, it wouldn’t hurt to brush up on the 40 Best Compliments to Give People Over 40. 
essential dating tips for men over 40

But remember the basics.

Some things never change: You should arrive on time, be present, take a genuine interest in who she is and what she derives meaning from, offer to pick up the tab, and see that she gets cab if she’s going home or stand outside while she enters her home safely. If she’s going to yours, always remember to solicit enthusiastic, verbal consent for everything you do. And unless you want to appear totally out of touch, avoid the 40 Sayings Men Over 40 Should Stop Using Immediately.
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Imagine your next relationship.

Before you sign up for every dating app you’ve heard your single friends raving about, imagine what you want this whole adventure to look like.
“Take some time to be alone, be comfortable being alone and with yourself, and decide what it is that you really want out of your next relationship,” suggests Jane Coloccia, author of Confessions Of An Online Dating Addict. “By getting clear about who you are and what you want, the right person will show up.” And when signing up for a dating app, keep in mind The 12 Biggest Dating Profile Blunders Men Make.
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Google yourself.

Again, your date will be Googling you. So correct misinformation they may find, or at least be prepared to prove that you’re not the escaped serial killer who shares your name.
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Figure out where you want to meet new people.

Some people like to meet potential dates at bars or cafes. Some like a set-up orchestrated by friends. Others prefer to go looking for love—or at least fun—online via the use of a dating app. It’s important to figure out what feels most natural to you and resist the urge to do what works for a friend. If you’re going the dating-app route—and, in 2018, we’d encourage you to—we’ve got your back: Here are The Best Dating Apps if You’re Over 40. 
Social profile, essential dating tips for men over 40

If you’re dating online, sign up to several apps.

“If you were catching birds would you place your bird seed in multiple places or would you have it in just one place?” says Megan Weks, dating and relationship expert. “Your odds of meeting someone increase when you are more visible, so take a risk and put yourself out there.” And to make sure your first date goes as planned, check out these 40 Irresistible First Date Ideas.
essential dating tips for men over 40

Don’t underestimate your appeal.

You may have a little less hair, a few more wrinkles, and a wider waist these days, but don’t let the reality of not being in your 20s or 30s anymore lead you to think that your appeal has diminished. Quite the contrary. Today you’re older, wiser, and should carry yourself with more confidence than you did in your 20s. And if you’re fretting your outdated style game, change that immediately after reading The 20 Definitive Style Rules for Men Over 40.
essential dating tips for men over 40

Get in shape.

Turning 40 means you’ve been losing testosterone for up to a decade. Consequently, your body composition has probably taken a hit and your lard-to-hard ratio is not what it once was. A bigger gut doesn’t just give you the silhouette of an older gent, it also poses the risk to diminishing your sexual function. The remedy is no great mystery: Hit the gym. And for more on aging, check out the 40 Ways Your Body Changes After 40.
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Get better about personal grooming.

If you’re back in the game after a few years away, you may be surprised to discover that you’re hairier than your younger male competitors out there. Now, you needn’t go all Ken doll on us, but if your chest, back, and privates are indistinguishable from those of a grizzly bear, a trim may well be appreciated.
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Sign up for shopping services.

We know: You hate shopping. That’s fine. But guess what?! In 2018, you don’t even have to leave your home to shop! Give reputable subscription services your sizes—and a general idea of your vibe—and they’ll send whole outfits to your home for you to keep or send back as necessary. Bombfell, Stitch Fix and Trunk Club all exist because of men who feel like you do about shopping. So update your wardrobe, and you’ll feel better and more confident. And if you’re shopping the old-fashioned way, know the 30 Best Ways to Save Money on Clothes. 
don't talk about work at the holiday party

Don’t date in a vacuum.

Seeing how your date interacts with other people will give you a much more well-rounded view of the person they are. Friends and family will bring out different aspects of your partners personality and behavior. You job is to figure out how you feel about these heretofore unknown traits.
essential dating tips for men over 40

Don’t make dates fit a profile.

“Sure, we may all have had a ‘type’ that attracted us in the past, but to find a quality partner, it’s time to grow up,” says relationship coach and author Laney Zukerman. “There are many potential partners out there that are diamonds in the rough. It’s not always easy, but think outside the box.”
essential dating tips for men over 40

Use recent pictures on dating apps.

While it’s tempting to want to lead with a picture of you in your late twenties, your date isn’t going to take kindly to the subterfuge when you show up looking your actual age. It may sound trite, but your attractiveness really does hinge on owning who you are, not who you were or indeed who you will be.
A good rule of thumb is to try and post pictures taken within the past 18 months: A window of time in which you probably weighed the same amount or sported around the same amount of hair. If you really want to show your adventurous side by posting a five-year-old picture of you summiting Mount Kilimanjaro, add a caption that notes the year. And be sure to avoid using these 40 Things Men Over 40 Should Never Say.
essential dating tips for men over 40

Be positive in your profile.

While being authentic is key, being a pill or a grouch is unlikely to have people salivating to spend an evening with you. More importantly, negativity is indicative of pain, which, by your 40s, you’ve probably experienced. “Everyone has baggage,” says online dating wingwoman Em Hammel of menaskem.com. “But your online dating profile shouldn’t give a girl reason to doubt you’re the well-adjusted guy you are. We’d rather learn about your baggage while also discovering all your amazing qualities. Then we’ll love you for you—battle scars and all.” And for more dating-app tips, here are the 30 Worst Phrases to Use on Your Dating Profile.
essential dating tips for men over 40

Avoid sounding generic.

You have to be original on dating sites or apps. Everyone is laid back and loves to travel and enjoys movies. Don’t be afraid to let your idiosyncrasies show, because no one wants a 100% basic bro. If they do, you don’t want them. You’re in your 40s! You’ve lived a life! Prove it!
essential dating tips for men over 40

Be honest about your situation.

Whether you’re dating online or IRL, at some point, you’re going to divulge your age, whether you have children, and so on. You may be tempted to fib or lie by omission in the name of presenting yourself as a youthful, free-wheeling bon vivant. While stretching the truth might help you attain or maintain the interest of a potential partner in the short term, it won’t be long before the reality becomes apparent and you’re still single.
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Be honest about your marital status.

“Lots of people who are married but living as single fool themselves and others into thinking they’re legally single,” says says April Masini, a New-York-based relationship and etiquette expert. “When it’s found out that they aren’t, everything hits the fan and allegations of lying and cheating are flung about. Remember, if you’re married but separated, you’re married. If you’re married and living single, you’re married. If you want to date married, at least be honest with yourself and those you’re dating. But best of all, if you want to be single, make sure you are—legally.”
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Optimize your home.

If there’s a chance that a date might be coming back to your place for a nightcap, make sure it doesn’t look like the sort of bachelor pad you’d expect a single 40 year old man to live in. Stow your games console, hide the gravity bong, tidy the place up, and air it out. A man of your age needn’t make the point that he’s living large, but he’d do well to show he cares about his surroundings. And be sure you don’t have the 40 Items No Man Over 40 Should Have in His Home.
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Don’t pick a 20s bar to meet your date.

Start making a list of all the places that check your boxes and are also conducive to a great date. Those items might include a great atmosphere, fantastic cocktails, great food, pricing that south of outrageous, friendly service, and flattering lighting (you are in your 40s, after all). Like dressing young, planning to meet up at a place with banging music and a predominantly mid-twenties crowd will definitely backfire.
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Don’t show up slovenly.

A guy in his twenties or thirties can maybe get away with rolling up for a date in a patchy beard, battered Vans, and dirty t-shirt. You can’t do this anymore. Give yourself a hard look and see what you could polish while still feeling like your authentic self.
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Dress your age on dates.

Avoid the urge to dress younger. “Dressing younger only serves to highlight your advancing years,” says Alex Wilcox, co-proprietor of New York clothing store Lord Willy’s. “You end up looking like a old head on a young body. This is in contrast to dressing classic—albeit with a few playful little touches—which tends to do the opposite.” And definitely wear nothing on this list of 50 Things No Man Over 40 Should Own. 
essential dating tips for men over 40

Get there before her to secure a table.

Ah, yes. The most important piece of dating advice for men: How to nail the greeting. Stand tall, flash those pearly whites, and give your date a greeting that’s both warm and not overly familiar. You’ll have to discern whether that’s a hug, a Euro-style double-cheek kiss, or a handshake. Tell your date that you’re pleased to see them and assuming that you arrived first—always a good move—make sure you’ve secured a well located table, a drinks menu to peruse, and the attention of your server. Guide your date to sit with their back against the wall so that you are not distracted by anything else going on around you.
essential dating tips for men over 40

Turn off your phone.

Or at least silence it once your date has arrived. Check it when your they use the restroom if you need to but make you stay present and engaged. And for Pete’s sake, don’t wear your phone on belt clip. Being dad age doesn’t excuse you from making a classic dad mistake.
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Use body language to your advantage.

“Keep your head high and shoulders squared off,” says Amy J.C. Cuddy, Ph.D., an assistant professor at Harvard business school. “Take up some territory by placing your feet shoulder-width apart. Don’t fold your arms in front of your chest; keep an open posture. Occupy extra space with your body language.” And for more on decoding body language, here’s how Read Your Partner’s Mind with These 10 Body Language Tells.
essential dating tips for men over 40

Be slightly carefree.

It’s so easy for a man in his 40s to get annoyed with terrible service or unruly neighbors on a date. Let it go, and don’t get rattled. If you get annoyed, she will only feel awkward.
essential dating tips for men over 40

Keep it light.

On a first date, you don’t want to get into an in-depth conversation about how you’re having a midlife crisis or how you hate your career. If all goes well, they’ll be time for some serious talks down the road, but in the early stages of dating, have some fun, keep it lighthearted, and ask a million questions. For help on that, here are the 20 Essential Questions To Ask On a First Date.
essential dating tips for men over 40

Hone your listening skills.

At the grand old age of 40, you’ve likely racked up some accolades and some great stories to tell. But don’t let yarns of your own derring do get in your way. Answer questions when they are asked, but as soon as you’ve delivered a brief and satisfactory answer—hopefully in a way that’s funny, intriguing, and charming—ask your date something you genuinely want to know about them and pay attention for interesting avenues of inquiry to explore.
essential dating tips for men over 40

Avoid detailed ex talk.

“It’s a big turn-off and it shows you haven’t moved beyond that relationship,” says Elliott Katz, author of Being the Strong Man a Woman Wants: Timeless Wisdom on Being a Man. Your MO should be to focus on your date and get them to open up, not wonder how they measure up.
essential dating tips for men over 40

Don’t let confidence come off as arrogance.

If you’re looking for dating advice for men over 40, you probably have quite a bit of life experience behind you. But that doesn’t mean you can have an ego. “There really is a fine line between confidence and arrogance,” says Jim White, founder of dating site Singles Over Forty. “While it’s great to sound confident and to even show a little ego while on a date,” White says you need to take “a second to listen to yourself and observe your own posture and mannerisms.”
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Show some pride.

But don’t be afraid to share some information that reveals a little about your personality and your achievements. Researchers at the University of British Columbia found that unlike arrogance, pride can be a turn on. They discovered this by asking women to look at photos of men exhibiting shame, happiness, and pride, then asking them to rate the guys’ attractiveness. When it’s your turn to divulge some information about yourself, it’s always a good idea to talk about something you take pride in. It could be sending your parents on a trip they’ve always wanted to go on, or coaching your kids little league team. As long as the sense of achievement you feel is genuine, your attractive display of pride will shine through.
first date questions, essential dating tips for men over 40

Seed the question.

If there’s a piece of information about you that you’re dying for your date to know but you can’t think of a way to seamlessly slide it into the conversation, try asking your date the question that you want to be asked. Once she’s answered your question, it’s very likely that she’ll serve the same question right back to you. And for more helpful advice, know The 20 Questions You Should Never Ask On a First Date.
essential dating tips for men over 40

Temper achievements with self-deprecation.

Being in your 40s means that you’ve got some life under your belt. That can be attractive, but so can a little self-awareness. Put them together and you can serve up an intoxicating combo like this:  “Yeah, I went to [insert prestigious college] but I was just about the worst undergrad they ever had.” See what I just did there? Your date will, too.
essential dating tips for men over 40

Know Your Deal Breakers.

If there’s one primary piece of dating advice for men over 40, it’s to know what you want. “When you know what you won’t tolerate, it’s easier to date smart,” says Masini. “For instance, if you don’t want to date someone who has kids, you’ll save yourself loads of time by simply saying no to anyone who wants to date you and who already has a brood. Same goes for money, religion, and lifestyle. Forget judgment—just be true to you and you’ll be successful at dating.”
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If you haven’t been dating for a while you may be surprised to know that most women will assume that they are paying for their share of the bill. On a first date, offer to pay without being overbearing. If your date still wants to pay, and you have a sense that you’ve shared a fun evening, suggest she gets the bill on your next date, should you be so lucky to see her again. And if you’re going on that second date, get inspired by these 40 Irresistible Second Date Ideas.
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Follow up.

Wanna see your date again? Tell her you’ll call them. Then call them. If you don’t want a second date, don’t say you’ll call them. Simply say: “I had a great time tonight.” Lying about your intentions will make you feel bad while they’ll feel lied to. And forget the three-day rule. We’re so connected now, if you don’t contact your date within a couple of days, you’ll seem like you couldn’t be bothered, or didn’t enjoy the date.
30 compliments, essential dating tips for men over 40

Set expectations.

It’s 2018. If after days, weeks, or months, your date is ready to be monogamous with you and you’re not there yet, be upfront about it. Similarly, if your date is looking to have children and your child-raising days are behind you, it’s imperative that you let them know before your lives become too intertwined.essential dating tips for men over 40

Don’t take things personally.

“Dating can require a tough skin. Start developing one now,” recommends Renée Suzanne, a dating coach. “Nothing that a stranger does online is really about you. Having a fulfilling love life is worth enduring a few setbacks. Hang in there!”

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Be open to their family situation.

Even if you’ve never had kids of your own, as you date in your 40s, you’re going to come into contact with all manner of co-parenting and step-parenting setups. “This may require flexibility as you work around ‘I have the kids this weekend’ or go on ‘dates’ with children involved,” says Monique Honaman, author and relationship expert.

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Don’t put your eggs in one basket.

There are several advantages to date multiple people before you’ve agreed on exclusivity with any one of them. It will sharpen your ability to find someone who is right for you and have more opportunities to know what makes a great date—and a not so great one.

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Think of each bad date as a necessary step towards a great one.

Some dates won’t be good. In fact, some may be so not good that you’ll be less inclined to go on another for a while. Resist that urge and arrange another date with someone new ASAP. If there are lessons to be learned from the dud one, be sure to apply them at the earliest opportunity.

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