5 Steps to Dating in Your 50’s

Who is this guide for?

This guide is exclusively for:


50 and older

Looking to get into dating

The dating scene has changed a lot, it seems like every week there’s new apps, terms and tips to get ahead in the dating world. This guide is here to hold your hand, it’s dedicated to the following:

  • Those who’ve come out of a marriage or long relationship, looking to get back into dating
  • Those who’ve tried dating, particularly online dating, but still haven’t had to much luck
  • Those who are over 50 but tired of the mature dating scene. Those are looking to enjoy themselves, meet interesting people and take part in new experiences
  • Those looking for love, lust and romance

“I was surprised that men in their 30s and 40s were interested in me!”

Sandra, 54

The 5 steps to over 50s dating

Setting Boundaries

Jumping right into the cold water can be a bit of a shock.

Dating can be exciting and thrilling yet what it’s you’re comfortable with is the most important. 

For many, dating is likely to be something that they haven’t done in a very long time. For others, it might be something they’ve never done. They married their first partner, they never had to do online dating or dating in general.

If this sounds like you, don’t worry.

Dating might seem a little daunting, however the key to taking that leap is setting boundaries.

Dating and relationships don’t happen all at once, it’s a long winding road full of exciting milestones along the way. The big milestones in the distance may seem a little scary; going on face-to-face date, that first kiss, having sex with a new partner!

But remember, you can enjoy the earlier, more comfortable milestones with no obligation to take part in the later milestones when you’re ready. 

Maybe you’re comfortable with chatting to someone over a messaging app, but not yet in person. Maybe you’re not ready for anything sexual. Maybe the idea of another long term relationship isn’t what you want. 

All of these are a-ok!

Take some time to think about your boundaries. Take a look at our boundary roadmap guide and see where you feel comfortable. Over time, these may change. Take some periodically to reassess the boundaries you feel comfortable with.

Understand the boundaries you have. Know that you never should forced to cross them.

While it’s important to know what your boundaries are, it’s also important to explain them to a potential partner. 

When messaging with a new guy, set out early what you do and do not feel comfortable with. Explain your situation, that you’ve recently come out of a marriage or long term relationship. Chat about the boundaries you feel ok trying to cross, but that it may take time and ask if they’re ok with that.

When you’re online dating, you’re likely messaging more than one person. This is normal and accepted. With so many people online and so little time to get to know them, being upfront is appreciated.

Be warned, you may feel like some guys will push your boundaries. They may show respect for what you’re comfortable with at first, but as you progress in your relationship, you may find them encouraging you to cross boundaries you don’t feel up to yet.

Gentle, playful encouragement might be ok. When things become too incessant, then you may have to intervene. 

Again, with so many people online dating, you are free to cut things off if you’re not happy. You are in control of your dating roadmap. You should try and challenge yourself to do things that are a little scary, but you shouldn’t feel coerced. Ending things because you’re not comfortable is ok. There’s plenty more people online ready to chat to.

Picking An Age Range

This is the fun part.

Dating has come a long way. A hell of a lot more type of dating is now acceptable and even encouraged. Don’t feel obligated to date a certain kind of person, and importantly, don’t feel obligated to date someone the same age as you.

Also, don’t think that as a mature woman, you won’t have interest from men in every age range. Again, dating has come a long way. Age-gap dating has exploded in recent years, don’t think there won’t be younger guys interested in women over 50. Because trust us, the opposite is true!

There are plenty of positives and negatives about each age range.

Ask yourself, what age man are you looking for?

20 – 29


  • Guys in their 20s are full of energy, perfect for if you’re looking for new experiences and wild thrills
  • Very sexually active and eager to please, if that’s your preference
  • Likely to be not looking for anything too serious, if that’s what you’re looking for
  • Likely not looking to have children just yet


  • May be a little young by many women’s standards
  • Again, may not be looking for anything too serious
  • May be too sexually focussed, pushing the boundaries you’ve only just set
  • May be looking for someone to help them financially

30 – 35


  • Still has the same energy and thirst for excitement as someone in their 20s, but with a sensible head on their shoulders
  • Again, still sexually active but more responsible and, importantly, experienced
  • May be looking for a something casual, may be looking for a slightly longer term thing
  • Likely to be financially independent


  • If you’re not comfortable dating a younger man, this age range might not be suitable
  • If your friends or family have more conservative ideas about dating, you might get some flack from them (even though it’s none of their business!)

36 – 40


  • While they may be more settled and less interested in adventure, this age range still has men who enjoy new experiences
  • Very responsible and mature, unlike some of their younger counterparts
  • Highly likely to be financially independent 


  • Would likely be looking for something serious, or extremely casual
  • May be starting to set in their ways, which may not be what you’re looking for



  • If you’re interested in someone your age range, then this is likely the place to start
  • Likely to be mature, responsible (although there’s plenty of childish ones!)
  • Would be accommodating if you have children, as they likely have some of their own
  • More likely looking for something serious, if that’s to your interest


  • There is a large percentage of men in this age range more interested in younger women. You might have to filter out those.
  • Older guys can be set in their ways, uninterested in new experiences or showing romance. This might not be what you’re looking for.
  • More likely looking for something serious, if that’s not your preference

Picking a site/app

There are a lot of dating sites.

Like, a lot!

Finding the right one for you can be pretty tricky. Each dating site/app has its positives and negatives, each attracts a different kind of guy. Take a look at our dating site/app breakdown to find the perfect platform for you.



  • Large number of users
  • Easy to download and use


  • Can be focussed too much on flings
  • High chances of “ghosting” (link)
  • App used primarily for under 30’s



  • Offers a wide range of relationship types, from casual to the more serious
  • Very good filtering options


  • Not a huge number of users
  • Many of the older guys are looking for younger women, plus there’s very few younger men looking for an older partner
  • Has a number of fake profiles

Telegraph Dating


  • Good for mature members
  • Offers a range of people looking for serious relationships


  • Many of the older guys are looking for younger women, plus there’s very few younger men looking for an older partner
  • Low number of members online and active

Staying safe

Online dating can be a fun and exciting experience, however like everything else on the internet – it’s important to stay safe. Unfortunately, for many dating sites/apps, scammers are prevalent. 

The ability to gain someone’s trust and to target vulnerable people makes online dating an effective platform for scammers. While their approach will differ from person to person, usually they involve posing as a potential partner, promising a dreamlike relationship, then asking for money due to a sudden and dramatic reason.

Dating online safely isn’t difficult, it just takes some know-how

Don’t worry, keeping a level and looking out for these top trends can keep you safe when dating online:

Reluctance to show their face

Many scammers online don’t use their actual profile, they will make a fake one using someone else’s details. Principally, they’ll use photos that aren’t their own. 

For that reason, they will be very unlikely to share more photos that aren’t already on their profile, or join a video call. Use this to your advantage. If you’re a little unsure whether a potential partner is genuine, ask them to send a selfie. Better yet, suggest a video call date. See how they react, if they are hesitant or flat-out refuse, be sure to raise your suspicions.

Poor English

It’s unfortunate, however many scammers operate outside of Western countries. This can make it difficult to catch and prosecute them.

However, this does mean many don’t hold a high level of English language ability. Their profile, which has likely been used several places before, may have perfect English. But you might find their messages are short, to the point and hold a number of grammar and spelling mistakes.

Of course, not everyone with poor English is a scammer online and you shouldn’t disregard someone purely based on a language ability. However, if you already have your suspicions, this may be a number mark in the potential scammer section.

Highly relationship focussed

Scammers like to target what they consider vulnerable people. These are individuals they see as very keen on a relationship, so much so that they ignore the warning flags. They’re really want to meet Mr. Right and are willing to ignore a few strange behaviours to get there.

For this reason, you may find a potential scammer’s profile to be extremely relationship focussed. While a normal online dating profile may say they’re looking for something serious, a scammer will go above and beyond. They’ll talk about how they are looking for marriage, looking to take care of a female partner, financially and emotionally. 

When chatting to them, they’ll escalate things quickly. Not in a sexual way, but rather in a romantic way. They’ll quickly talk about “love” and how infatuated they are. They’ll also be keen to move from the dating app, to messaging on a WhatsApp or a similar messaging service.

Military or similar trustworthy career

As many scammers’ profiles are used in several places, some key traits can be regularly spotted.

You may find the member shows off that they are/were in the military. Military photos are extremely common for scammers. If not the military, you may find another similarly trustworthy job. It can make the profile seem more genuine, it also gives them an excuse to explain long periods of silence or their different time zones. The scammer’s financial issues (which they use to ask for money) usually involve travel, which you can expect from someone in the military.

You may also find frequent religious references and frequent admission that they are “God-fearing”. Again, this is to show trustworthiness, that their actions are not vindictive as they are a moral individual.

Asking for money

Eventually, all scammers will show this trait. Be on the lookout and be sure to never give money to someone on a dating site.

This may be harder than it sounds, it could be after a long and emotionally fervent relationship online. This individual may seem perfect, they may have promised a lot and made you feel extremely happy. However, be sure to end things quickly when the topic of giving money comes up.

They’ll spin a sob story, talk about how they are in grave danger, either financially or have a threat against their life. Be firm and leave quickly, no matter the circumstances, a scammer should never be indulged.

Join a site with a verification system

Your dating site/app is there to protect you. If you are ever unsure about whether a person is genuine or not, flag their profile up to the site’s verification team. They can tell you quickly if the person is a scammer.

However, before all that. Ensure the dating site you join actually has an active and engaged verification team. 

For example, Toyboy Warehouse has an inhouse team of verification experts. Every profile is manually approved to ensure all members are genuine. The team is also on hand to address any and all concerns, they are happy to check a member for you if you’re ever unsure – regardless of why.

Dating terms

If you haven’t dated online for quite a while, or have never tried it before, the host of dating terms and traditions may seem a little overwhelming.

Honestly, our advice is not to get too bogged down in the minutiae. Online dating is intended to be fun and exciting, an opportunity to meet new people and experience new things. It’s not something you need to learn or acquire a totally new vocabulary about. 

However, you may find some of them useful, especially if you’re going to experience them in your dating adventures. Here’s a snapshot of the most important that you’ll likely benefit knowing about:


While not exclusively about dating, FOMO stands for the Fear or Missing Out. With our modern interconnected world, there’s arguably a host of more things to experience. With access to millions of films, TV shows, songs, books, podcasts, stories, social media posts, etc., one can be stricken with the feeling of FOMO. The idea that with so much to choose from, it can be difficult to make a choice as something better may be on the horizon.

The exact same concept can apply to dating. Instead of a handful of potential partners, people are exposed to hundreds. When searching online, you’ll likely find pages and pages of suitable candidates. 

With so much to choose from, it can be difficult focussing your attention on just one person. Many people start to feel anxious that the person they’re speaking to isn’t the best possible person for them. Even if nothing has gone wrong, the hundreds of potential other partners are just waiting for them and they start to feel fear that they’ll miss out on someone even better for them. 

If you spot yourself experiencing this, be sure to try and limit your fears. FOMO can lead to a paralyzing inaction, that if there’s always a better prospect out there you’ll never settle on one person. When you get chatting with someone and start to feel a connection, try to limit your searching and ignore other incoming messages. Remember that you’re only getting a snapshot of this person online, if you continue to feel there’s someone better, you’ll never stop searching.

Of course, you may be on the other end of FOMO, if that happens you may unfortunately experience “ghosting”.


As the name might suggest, ghosting is the process of suddenly leaving someone’s life. For online dating, when you “ghost” someone you just stop replying to their messages. This might be when you were a few conversations in, it might even after a few dates, or when things were starting to get serious.

Ghosting is regarded as not the nicest thing to do, if it’s early days with someone it’s not as bad, however a short word explaining that while you had fun, you’re not looking to progress with a relationship, is usually expected.

Cuffing Season

Cuffing season is the period of time usually around early autumn to late winter where you might find your dating prospects get a little easier.

These cold, winter months are usually a little lonelier for people, they’re less likely to go out with friends and meet new people. The fun of the hot, summer months has passed and people are looking for someone to curl up to during the cold nights.

This is cuffing season, the period of time where people are more open to relationships. They’re more keen to couple up and find someone to spend the winter evenings with. 

Be warned however, it’s called cuffing season as some regard it as the time when you’re metaphorically ‘handcuffed’ to someone, only for spring to set you free. 


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    Oluwasegun Ogunjana

    I seriously want to know how suitable it is at my age, (52)

    • Avatar

      More than just suitable. Online dating & age-gap dating is wonderful in your 50’s.

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