You’ve still got it.

Love can often feel like a young person’s game. But after a divorce or bereavement, you might well be looking to get back out into the field and find long-lasting contentment (and maybe even some excitement while you’re at it). How do you start dating again once you hit 40?

The first step is getting past the negativity.

With a back catalog of exes and negative experiences, it’s no wonder dating at 40 seems like an all-access pass to the Whiny Club. A simple, elegant dinner date can turn into a dumping ground for resentment, complaints about past treatment, and ill feelings toward exes.

You might end up sitting in front of someone who talks nonstop about their ex. If one date turns into several, that bitterness toward their ex gets reflected onto you – everything you do right is compared to their ex, making your date emotional. Everything wrong you do makes them angry – because it reminds them of their ex. How can you win? 

A lot of potential partners in midlife are also super defensive. Often, divorces aren’t a matter of black-and-white morality – they usually stem from a breakdown in communication over time. But if you’re single at 40, you might think it carries a stigma that you need to defend.

“I’m divorced, but don’t worry – it was entirely their fault.” If you had a dime for every time you heard that on a date, you’d be able to pay their lawyer’s fee yourself. Don’t present yourself as perfect, but know that you need to manage your expectations as well as theirs.

Falling in love is one of the best feelings in the world, but having your heart broken is the opposite – and a potential relationship can be long, tiring, and full of unexpected twists. During midlife, it’s best to approach dating sensibly, wisely, and with caution.

Take the common-sense approach, and you’re more likely to find lasting companionship that doesn’t lead to further heartbreak.

Let Team Vippi be your wingman and walk you through the basics of finding romantic connections during midlife.

A timeless classic: 12 tips for dating in midlife

As this clip from The 40-Year-Old Virgin shows, dating is no picnic during midlife.

It’s a different rulebook to dating in your twenties. But it’s certainly possible to experience excitement, fulfillment, and longevity as a midlifer in the dating market.

1. Avoid dating while separated. Get a divorce first.

The start of a new relationship should be fun, sparky, and unburdened by baggage (as far as that’s possible in your forties).

You might be itching to get back out there after a nasty separation. But until the ink is dry on those divorce documents, don’t entertain the idea. It’s not over until it’s over, and separation may draw estranged partners back together once they realize the stakes at play.

Jumping the gun isn’t fair on whoever you’re dating, your current partner, or you. Work on closing one chapter as smoothly as possible. Then, progress to the next with a clean sheet and on your terms.

2. Don’t use physical attractiveness as your North Star for picking partners.

It’s a simple fact of aging – your value on the sexual market value declines over time. This is a time of significant change for your body, as it will be for your partner. So qualify them based on timeless values like compassion, smarts, emotional intelligence, and stability. And one of the most overlooked traits is cheerfulness. Such a trait is rare. Imagine being with a sullen person day in, day out. If you find cheerfulness in a person, keep them. They do wonders for your soul.

Avoid focusing on physical attraction alone (and that goes double for men who seek much younger partners). The younger person in the couple could find other parts of you more attractive than your values and personality, like your wallet.

Instead, find compatibility in other areas. Ask about values, how they see family, and where they spend their festive winter period. Do your politics align? Are they religious? Think about how the characteristics you’d want to see lined up with your own, and qualify their suitability based on those.

Also, figure out how you resolve disagreements. If you have a difference of opinion on a particular topic, it’s essential to know you have a robust dynamic that doesn’t break under pressure.

3. Everyone else your age in the dating pool feels as weirded out as you do.

No one planned to be dating again at 40. Women are rethinking their bodies, men are entering prime midlife-crisis territory, and everyone feels a little uneasy.

If you’re healing after traumas like divorce or bereavement, everything can feel a little off-center. You might constantly compare your new partner with your ex, or you may simply have forgotten how to have fun ideas on your own after a controlling relationship.

Weirdly, knowing that most people in the dating arena at 40 feel insecure or jaded should make you feel less so. Many, many of your potential dates will be in the same boat. Allow that to be a connector rather than a barrier.

4. Stand out and embody your success.

Don’t half-ass it. Dress to impress in a way that suits your personality, but don’t try to look too young or dress just like everyone else.

If you have the funds, it might be worth seeing a personal stylist before you get back out there. If not, a fashion-forward friend or family member may be able to help you switch up your repertoire in a way that suits you.

We can get too comfortable in middle age, but we don’t have to resort to a life of fanny packs and company Sports Day polo shirts.

To succeed in dating as a 40+-year-old, differentiate yourself from others on the scene. And not just in how you look, either.

As a midlifer, you might find that your passions have been replaced by burdens, responsibilities, and the trappings of a long-term relationship. But if you’re passionate about various aspects of your life, your natural enthusiasm will come across effortlessly. This will make you different from the complainers your date will have met on the way to you.

This is a perfect opportunity to invest in your unique interests and lifestyle choices. Take the time to enjoy life again. This will help you dodge the Moaning Trap that befalls so many 40/50-year-olds in the dating arena.

You won’t embody success if you don’t feel successful, so ask yourself – what does success mean to you? Money? Time to work on your passions? Social capital? Being present for your family? There’s no correct answer, but make sure you pick a perspective and start working toward your goal outside of dating.

Show your date what you bring to the table, and work out what they bring, too. You don’t have to start a relationship with the first person you meet. Be selective, and give a strong account of yourself. Be a chooser, not a beggar.

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A bit of a fixer-upper: Date at your level.

Be wary of trying to ‘fix’ your date to suit you.

This rarely produces any tangible results, and it’s not realistic. The person you see on the first date will stay pretty similar throughout your relationship. Make sure you’re attracted from the get-go – “not being lonely” is a terrible reason to invest time and energy into someone.

It’s important to date at the same ‘level’ you are now. The closer you and your partner are in income, age, intelligence, and personality, the less fixing either partner will expect. Avoid dating someone with a far higher or lower income than you – ultimately, one will end up feeding off the other, generating resentment.

A relationship with too vast an intellectual gulf, for example, will turn boring very quickly. Even with age differences, you’ll soon realize that the generation gap prevents the two of you from unifying as individuals, as you’re at different stages of life with different expectations.

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5. Give off optimistic vibes.

Show your partner that you’ve still got plenty to look forward to. Approach midlife as an adventure, despite your memories of previous relationships.

You aren’t your job or your responsibilities. The damaging actions of your ex don’t define you. You’re a fully developed human with way more experience than while you were dating in your teens and twenties.

Optimism also means showing the individual sat across the table from you that you’re not jaded by your experiences with other people. If a bitter divorce doesn’t dim the light of your personality and your ability to have fun, it sends the signal that you’ll be able to handle the other stuff midlife will inevitably throw your way. 

6. Use humor effectively and sparingly.

If you crack jokes constantly, it might well be a sign of insecurity – but you still need to have a sense of humor. Dad jokes are a trap to avoid at all costs. Don’t lean on setups, puns, and wordplay. Instead, gentle teasing, cheeky asides, and reactive responses help you connect at a humor level.

Focus on reactive humor rather than barraging your date with jokes (unless prompted). It means that you’ll learn to read whoever’s in front of you. Some partners like a more serious, grounded, quiet person. Others want a partner who’s the life of the party and spreads smiles.

Being able to bounce off your partner’s dialogue will help you read the content of your date’s speech and respond in a way that boosts the overall mood.

In midlife, you might not have the body or hairline you once did. But humor is forever, and it only gets better over time. The better you know someone, the more in-jokes you can build together.

7. Launch a charm offensive.

Charm, intelligence, and etiquette play much more of a role as you get older.

You don’t have to be corny, but you do need to make more effort. Play the role of a classic gentleman or lady.

Charm isn’t just about swagger, charisma, or impersonating Cary Grant/Audrey Hepburn, though – it’s also about treating people right. Watch how your partner treats the restaurant servers. Do they display charm, patience, and social skills? Or are they rude and abrasive?

Charm is an excellent way to filter out potentially toxic people.

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A pre-dating emotional checklist

You are no longer fresh out of college with no attachments. You’ll likely have children, emotional baggage, and a heap of responsibilities.

• Are you ready? At this age, dating requires a little dedication and discipline. Will you put in the time on dating apps to find suitable people? And, what’s more, are you emotionally ready? A bereavement or traumatic separation can make midlife dating difficult. If you aren’t ready, don’t start just yet.
• Can you compromise? Your next partner is probably going to be in a similar position to you. Are you able to settle for a less-than-perfect person? And what aspects are you happy to compromise on? There’s no correct answer here – but asking this question can help you work out who you’re looking for.
• Are you looking for a long-term connection? If you’ve left a 20-year marriage and are back in the field again, is another long-term romance something you need? Or are you looking for a different dynamic? Being honest with yourself means you can be upfront with potential partners and avoid awkwardness.
• Can you handle a stepfamily? Stepfamilies are not easy – and if you’re looking for love at 40 and above, this is a question you’ll need to ask. How ready are you to take on the responsibility of someone else’s children? You’ve probably got a lot of fights on your hands to reach a place of peace and equilibrium in a blended family. 

No one is holding a gun to your head, forcing you to re-enter the dating field at a time that doesn’t feel right to you. So don’t go searching for a new partner until you’re ready.

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8. Remember that you’re still a sexual person.

Don’t let insecurity get between you and your inner tiger. Sex certainly isn’t the only defining factor in successful relationships, and your sex drive may well have reduced over time.

Our earlier sex lives are defined by adrenalin, serotonin, and dopamine. These are hormones that revolve around excitement, pleasurable sensations, and gratification. As time moves on, oxytocin, or the hug hormone, becomes the dominant hormone. Oxytocin has us seeking sexual connection from a calmer place.

So no, you probably don’t have the libido you used to – but it’s still there. And your date has theirs, too. Otherwise, they wouldn’t be sitting at the same table as you. Sweeping sexuality out of the way for fear your date might not be interested isn’t going to get either of you to a second dinner – or the bedroom. 

Let your date know you find them physically attractive, and don’t forget to flirt actively. State your intentions, too – if you’re looking for no strings attached fun rather than a committed relationship, make that clear. Showing your full hand at the start of a date is direct, sexy, and a great way to avoid miscommunication as the night draws on.

Even when you’re looking for long-term love, don’t leave sex out of the equation. Accessing your sexual side can help you maintain your confidence. If you’ve made clear that sex is on your mind, and they’re still talking to you, it’s a sure sign that (at the very least) the idea of sex with you isn’t wholly off-putting.

It may not be a priority for you anymore. But don’t forget about sex.

9. Stay on top of personal baggage.

More years = more responsibilities = more problems. Stay on top of your sh*t. You might have kids, an insane workload, elderly parents to care for, and any number of medical or financial concerns to work through.

That doesn’t exclude you from love and companionship, even though it can eat away at the time you can invest in your dating life.

Get your house in order before thinking about bringing another person into your life. It isn’t fair to drag a new partner into your whirlwind of demands, even though baggage will likely be part of the picture for anyone dating during midlife.

Make sure you at least have contingencies in place to make starting a new relationship easier. For example, if you’re caring for an elderly relative, wait until that person is in full-time care so that you can make sure their needs are tended to while looking after your own. 

Alternatively, get a sibling to step up if you’ve been bearing the brunt of the load when it comes to caring for relatives. You deserve your shot at happiness, too.

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Researching your partner online is just due diligence – up to a point.

You might think it’s creepy. But scoping your date online is pretty standard practice these days. It’s still preferable to let them create their own first impression. After all, wouldn’t you want that chance? Sometimes, however, people can’t help it. Maybe you’ve been hurt and want to make sure you’re not heading for another fall. 

Plus, dating during midlife means you don’t exactly have time to burn. If you arrange a date, it’s critical to know that you’re not wasting your time or theirs. If you aren’t comfortable becoming a potential step-parent, for example, and see that your date has five kids, you may need to be forthcoming about your feelings ahead of time.

Here’s how to learn more about your date before you meet:

• Why not ask them what you want to know straight up? If you’ve met on an app like Tinder, you’re already engaging in dialogue. If you share a little about yourself and ask them something, they’re likely to share in return.
• Search them up on Facebook as best you can. Most people have a Facebook account. Narrow down search results by the profiles in your area if there are several people with the same name, and check whether you have any mutual friends.
• Give them a Google – it’ll show you any public-facing materials they may have. If they’ve, say, been arrested or had news articles published about them, Google is where you’ll find that information.
• Look them up on LinkedIn (although it shows you who’s viewed your profile here, so you won’t be quite as stealthy). This shows you how they approach their professional lives and what they do.
• Take anything you find in your stride. Unless this person shows up as a notorious serial killer in their state, seeing information out of context is rarely helpful for painting the complete picture.

Your date has almost definitely looked you up, too.

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10. Control the pace of the date.

Modern dating usually starts online then progresses to a phone call. After that, Zoom or an in-person venue awaits. 

At each stage, take the lead on progressing your interaction to the next step. Be the one to call. Suggest places to meet. Being proactive shows that you’re fun, forward-thinking, confident, and unafraid of conversation. These traits are attractive at any age.

In midlife, and perhaps among divorcees/widows, it might be worth laying down some ground rules, e.g., not discussing your previous marriages until the fifth date or not talking too much about children, as you want this time to be about each of you.

Don’t be afraid to set the pace and the terms of engagement.

11. Ensure that sexual boundaries are clear.

Some guys think it’s okay to get frisky after the first or second date, but they need to respect boundaries. The only way to set clear boundaries is by being upfront.

If you’re not comfortable sleeping with someone until the fourth date, make that known before you meet. Being forthright about sexual expectations is not a red flag in and of itself. But pressuring a date for sex despite established boundaries is a massive sign that an individual cannot be trusted.

12. Spend a whole bunch of time together.

When you’re younger, dating is about making your partner want more – and it still is, in some aspects. 

However, that’s not achieved by aloofness and scarcity once you hit 40. It’s about showing you’re a great companion who still knows how to have fun, talk about deeper topics, and demonstrate stability.

Your partner is going to want to know you can hang out for long periods. Don’t hold yourself back. Go on long walks, play games together, and relish your time together. You don’t have to pretend you don’t care. You also don’t have to let your vulnerability act as a barrier – let them in.

Online dating gets a bad rap, but it’s your friend.

Online dating is no longer the stereotypical realm of basement-dwelling saddos. Instead, it’s become one of the key ways people meet each other, and those over 40 are no exception.

The best dating in midlife sites and apps

In Team Vippi’s experience, the best online dating platforms for people aged over 40 include:

• eHarmony: This site is more or less the benchmark for folks searching for long-term love. The algorithm for matchups is spot-on, and the fact it’s a paid service means that the timewasters are largely filtered out.
• Bumble: This app is similar to Tinder, but women are the only ones who can initiate conversation (unless the users are gay, in which case it’s a free-for-all). This means that women are (mostly) protected. The male users know that any conversations are starting from a place of genuine interest.
• Lumen: This app filters out potential timewasters by limiting the number of times a user can initiate conversation. This means that when someone reaches out, it’s to foster a genuine connection. The app is also exclusively for people over 50 – finally, someone sees us!
• Hinge: This is closely linked to Facebook, a social media network most midlifers use. Potential connections will always be from your friends-of-friends network, limiting the number of pervy randomers who might creep into your inbox.

Dating In Midlife 101: How to kick it off in style

So, you’ve got the right mentality, you’ve made it past the gatekeepers of online dating, and you’re getting ready for your first date.

First date questions

On a first date, you want to get to know your date’s values quickly. For that reason, you should ask questions that point to their qualities without getting too deep or bringing the mood down.

They should bring up happy memories for your date – far from the Whining Club we mentioned in the intro. You should be fostering positive emotions. That way, your date will associate you with feeling good, rather than thinking about their hangups.

For example:

• If you could turn invisible, what would you do?
• How do you feel about pets? Do you have any?
• How many children do you have – and what are they like? (Unless you’ve set “no kid talk” as one of your parameters ahead of the date).
• If you could take me anywhere right now with a click of your fingers, where would it be and what would you want to show me?
• Who are your special people?
• When I was younger, I sh*t my pants on a ski slope. What’s the most embarrassing thing that’s ever happened to you? (Team Vippi can confirm that this has worked in real life.)
• Would you rather fight a lion-sized duck or ten duck-sized lions?
• What’s one quality you have that no one else has?

First date protocols

These days, a first date might even be over Zoom – a glass of chardonnay at home during a getting-to-know-you session. Once seeing people face-to-face is a thing again, it’s best to choose places you love. 

People love a date who takes the lead! “I know this great place” is all you need to have someone agree (but don’t suggest a Brazilian steakhouse if your date’s profile says “vegan”). They’re agreeing to meet you, regardless of venue. But you should still pick somewhere that promises a great time.

The venue needn’t be outstandingly classy – you don’t want to look like you’re showing off – but choose a tasteful place with low lighting that’s close to other venues you could whisk your date off to afterward.

Who pays? Look, it’s the 21st century – we all know that the expectation isn’t 100% on the man to pay. But he should at least offer and should at the very least suggest paying for a taxi home.

Safety factors. The sad truth is, you never know who you’re meeting up with. Women especially should have a friend they can contact to confirm a safe arrival and departure. Make sure you have an app like Uber installed so you can make a swift getaway if needs be, and always be sure to meet in a public place surrounded by people.

How to flirt without being sleazy

As a midlifer, you might have lost touch with your sexy side. This might make flirting seem like an impossible task.

Don’t sweat it! Team Vippi has the ultimate cheat sheet for non-sleazy flirting:

• It’s not what you say, but how you say it. A flirty compliment delivered with hunched posture and eyes that are darting around won’t inspire trust. If you’ve got open body posture (unfolded arms, for example) and you’re making eye contact, you’re going to seem more confident in yourself, and they’re less likely to be creeped out.
• Context matters. If you’ve met a date online and you’re flirting with them, they’ve been through a whole filtration process (messenger chatting) and decided they’re at least interested. It’s not sleazy to tell them they look good. But if you flirt with people on the train home from the bar without context, they’re probably going to see you as creepy.
• Don’t come off as desperate. Flirting way too much can come off as desperate. It’s the same with reeling off cliched chat-up lines or talking way too much. Even though you don’t have to be aloof, don’t try insanely hard either. 
• Use innuendos – but level up to anything too explicit. Everyone loves a cheeky joke or a sexual pun. But being either a) too relentless with innuendo or b) too explicit can put someone off. So test the waters – start mild and veeeery gradually work your way up in terms of sauciness. If they don’t react or look put off by dirty humor, pull back a little. Always be reactive with your humor.
• Mirror their body language. The best way to sync with someone mentally is to do so physically. If they move close to you, move closer to them. If they stroke you on the arm, know that that’s now part of the language you can use to communicate. It’s a delicate dance, but one that makes sure both of you are comfortable.

After the first date

There’s no harm, at the end of the date, in deliberately downplaying your enjoyment of the dinner for comic effect. “That was above average. I guess we could see each other again.”

You’ve set up the idea that you enjoyed the date – so wait a few days to re-establish contact. This is the best way to avoid being clingy but confirm that you’re still interested.

The invite for the next date should refer to an in-joke you guys laughed about in the first. “I think I’d like to find out more about that time you fell over in front of Keanu Reeves. Can we meet up again? I have… questions.”

The next time should also be a different vibe. If you went out for dinner, maybe catch a show together, or go for a stroll along your nearest waterfront. Perhaps you can offer to cook for your date at home.

You’re just two people who had fun once arranging to spend some more time together, that’s all. Have that in your head, and setting up your second date won’t be so difficult.

It’s not always such a brilliant experience, though. If you want to let your date down gently, just be upfront in a brief text message. 

“Hey, I had fun tonight, but this isn’t really what I’m looking for at the moment. Thanks for a good time, and best of luck on your journey!” No one likes to get a text like that, but it’s as forthright and gentle as you can be. Make a clean break, and onto the next opportunity for connection.

The Roundup

Phew.

It seems like a lot to bear in mind, this midlife dating business. But fear not! Online dating means you’ve got more windows into the world of dating than ever. So a divorce needn’t be the end of your love life, and you certainly don’t need to become one of the people hung up on negativity and previous letdowns.

When the time is right, getting back out there could help you find companionship that’s even more enriching than your first time around.

Team Vippi unanimously agree that some of the best moments in our lives have been due to relationships. The excitement, the anticipation, the union. Bring that emotional energy back into your life.

Article resources

Felman, A. (2020). How to tell if your relationship is changing in the right ways. https://greatist.com/live/relationship-changes-over-time 

Krueger, A. (2014). https://www.forbes.com/sites/alysonkrueger/2014/04/30/the-best-ways-to-research-someone-you-meet-online/?sh=202ee10e2cde 

Oxytocin. (2020). https://www.yourhormones.info/hormones/oxytocin/