Dating Over 50: Your Guide to Meeting Singles and Building Connections

Dating Over 50: Your Guide to Meeting Singles and Building Connections

Today we are going to dive deeper into how you can meet singles over 50, ways to make them feel special, planning better dates, the red flags, and many other things. 

The joys and challenges of dating later in life 

Dating later in life is great, and dating around your 50s and 60s is the golden spot. 

Senior dating at later life stages can be somewhat complicated by health scares and limited mobility. Dating in your 30s and 40s is often burdened by having to decide whether or not you want a family and start working on it right now, juggling it with career and other things somehow. 

At 50, you’ve probably already made the choice of how you want to live your life, and you can relax into the relationship without having those thoughts running constantly in the back of your head. 

Also, when you’re dating later in life, you’re still young, right? Maybe not by the Gen Z standards, but regardless. You’ve got all this energy, things you want to do, and places you want to go to. Having a cool person by your side to endeavor all those things with is enriching and stimulating. 

Being alone at any stage in life can feel lonely at times. As we grow older, we crave someone’s company and we crave emotional connection too. Some people will say no to dating though because they’re traumatized by the past and are still healing from previous relationships. But there’s no need to deprive yourself of love. When you’re 50 and older, you get to decide what your relationship will look like because there is no right or wrong really, if you think about it. You have the freedom and the power to redefine what love and romance look like for you. 

Breaking the stereotypes about singles over 50 

There are so many stereotypes about dating for older age groups, it’s not even funny. When you think about it, back in the day romance was reserved strictly for young people, and everyone over the age of 30 was no longer considered young. 

Thankfully, society has come a long way since then, but old habits die hard. Here are some of the most painful (or, should we say, ridiculous) stereotypes about dating over 50.

1. Anyone who’s 50+ and single is lonely. In reality, many choose to be alone until they find someone they’ll truly like.
2. People over 50 are not interested in dating. Of course not true! With that logic, they shouldn’t be interested in fine dining, traveling around the world, or living in comfortable nice houses. 
3. If you’re single at 50, it means something is wrong with you. Many people split from their partners later in life which often indicates their emotional maturity, as they’re not willing to stay in a relationship where they’re unhappy. 
4. Everyone in their 50s is set in their ways once and for all. Some people are, but many remain flexible and open to new formats of dating and living. 
5. At that point in life, you can’t have fun anymore. Older people are human too. 

Tips for Online Dating Over 50 

Choosing to sign up for a dating site for over 50 is a great idea if you want to find wonderful people from all over the world and date outside of your usual bubble. 

Here are a couple of tips for anyone trying out online dating over 50:

1. Choose right. Not every dating site for over 50 will fit you. Watch out for their positioning and business focus, and see if it aligns with your dating goals. The Once dating website, for instance, is all about mindful dating, and some other sites can be sex-only. 
2. Pay attention to your profile. People judge books by their covers in online dating, make sure your photos are bright and reflective of who you are. Fill in some information about your lifestyle, hobbies, and dating goals. 
3. Don’t be afraid to initiate conversation when you match with people you like. It’s not that deep who texts who.
4. Stay safe. Don’t share too much with strangers, never send money if someone asks for it, and always have first dates in public places.  

Red Flags When Dating in Your 50s 

Here are some red flags for dating over 50.

• Conflict avoidance
• Inconsistent communication
• Emotional unavailability
• Unrealistic expectations 
• Excessive control of your life 
• Disrespect for your boundaries
• Focus on their past relationships 
• Financial immaturity 

Dating Advice for Women Over 50 

Dating in your 50s as a woman is an exciting journey. 

• You’re in the prime of your life
• Have a lot of experience in dating
• Know what you want
• Probably done with having babies, so that’s not a concern 
• Not falling for cheap manipulation tricks 

Now is the time to live your best romantic life and date only the people you’re genuinely into. No more compromising or sacrificing! 

Here are a few recommendations we can give to singles over fifty who are only considering dating again:

1. Build confidence in your age and social status. Women were shamed for aging and not being the young girls anymore throughout history. Don’t let those kinds of comments or insinuations get to you. All those so-called societal norms exist only to control women, and nobody should fall for that. In their 50s, women feel confident in their skin, look great, and have lots of experience. All those things should be celebrated.
2. Drop the impressing game. Focus on being authentic and genuine when you’re dating. Aren’t you tired of trying to impress people anyway? If somebody doesn’t want you just the way you are, they don’t deserve you, and you shouldn’t waste your time on them.
3. Explore new social circles to expand your dating pool. There are many places you can meet someone besides a bar and a dating website. Go to different workshops and classes, join community groups, and pick up hobbies where you can meet new people, ideally from a different social bubble that you’re used to. Do it not only to find a romantic partner but also to add something new and fun to your life. Now that’s what we call multi-tasking! 
4. Give online dating a try. No, seriously. Even if you’re really shy and have never done it in your life. Even if some of your friends had a negative experience with it. Even if you’d rather not. Everything new is scary, and meeting people online can give anyone anxiety. But imagine missing the love of your life only because you were too scared to sign up on a dating website. What’s scarier, that, or giving a new dating format a try? 

Here are a couple of tips for when you already started dating over fifty:

1. Talk openly. Don’t beat around the bush or speak in riddles. Nobody has the time for that, especially not you. 
2. Be clear about your intentions. Whatever your goals for dating are (sex, love, marriage, casual romance, something entirely different) – tell your prospects about them. It will only make your internet dating over 50 better, as you won’t have to type away for days with people who want something entirely different. And don’t worry about saying it in person either. People appreciate honesty if you’re not cruel about it. 
3. Be open-minded. No matter what anyone says, dating over 50 is the best time to broaden your horizons and try to date new kinds of people, go to different types of dates, and experiment in the bedroom. You may think that you’ve found yourself and know what you want, but how exciting is it to try something new! Who knows, maybe there are parts of you that you didn’t even suspect existed. 
4. Establish boundaries from day one. Relationship boundaries are wonderful for managing expectations. You both will know what’s preferred, and what’s off the table. Don’t forget to agree on what happens if either of you repeatedly breaks the rules, and follow through with those penalties. 
5. Maintain your independence. Especially if you’ve already been in a long relationship or a marriage before. Dating while being somewhat independent is wonderful because you can maintain your lifestyle and other relationships while enjoying all the perks of being with someone you really like. 
6. Learn from your past but don’t compare too much. Dating for women over 50 can involve a lot of comparison with previous partners. There is nothing wrong with it per se, but try not to rely on your previous experience too much. Every new person you’re dating is unique, and if you insist mentally that they’re just like your ex-lover, it won’t do any good to your love story. 
7. Be safe. Sadly, women can end up in unsafe situations through no fault of their own at any age. Don’t share too much information with new people you meet, go on dates in public places, and let your friends and family know your plans. Also, if you get a weird feeling about a person, walk away. It’s better to risk being perceived as rude than to endanger yourself. 

Lastly, have fun! Enjoy the process and have the time of your life. Don’t stress too much about meeting a perfect person or spouse material. Focus on living every day with a smile on your face. 

Dating an Older Woman in Her 50s 

Are you interested in women over 50 and dating advice? We’ve got you! 

Fewer stereotypes, more genuine curiosity

There are preconceptions about women of all ages, and the older women get, the smaller the box that society tries to fit them into. Avoid doing that when you start going out with an older woman. Every individual has their own story, and every woman in her 50s and older can surprise you if you let her. 

Embracing her independence (and life experience)

Something you can do less of to make your dating over 50 a more enjoyable experience, is to let the woman you’re dating have her independence and judgment. At 50 years and older, we’ve all had plenty of events in our lives and time to think them through which makes us experts in how we should go on, no advice necessary. Having said that, your input is welcome and appreciated, as long as you’re not intrusive. Avoid giving off the “I know what you should do better than you” type of energy. 

Honesty is the best policy

When they get to their 50s, many women grow incredibly tired of the BS associated with dating. Don’t try to be smart and play them. Or do it, but know that women probably see through you and simply entertain themselves by watching you do that. If you want a chance with her, don’t embarrass yourself like that. 

Also, make sure you know what you want from dating, and share your goals openly. Some men will hide the fact that they’re not looking for anything serious because (going back to our first point about stereotypes) they’re sure that every woman in this age group is dying to settle down. It’s simply not the case though. 

Here is what you can expect when dating women over 50 

• Emotional maturity 
• Confidence in how they look and what they do 
• Wealth of life experience
• Focus on staying independent 
• Clarity in expectations from a relationship 
• Directness and focus on honesty 
• Priority of mental and physical health 
• Family involvement – either her parents or/and her kids
• Little interest in meeting societal expectations 

Dating Over 50 FAQ

What is a red flag when dating in your 50s?

Many red flags are timeless and apply to every age category. However, watch out especially carefully for emotional unavailability as they will not change at that point, and you need to decide whether you’re ready to tolerate this. Also, excessive focus on their ex is weird and worrisome. Obsession with controlling you, including your financial habits, is a serious red flag too. 

How hard is dating after 50?

It all depends on your goals and focus. Finding a perfect match is difficult at all stages of life, but it’s doable. Also, depending on your past breakup, you’ll have less or more difficulties opening up again. 

What are the chances of finding love after 50?

We can’t give you an exact percentage, unfortunately, but the chances are good. A lot is in your hands though. You need to put yourself out there, go to new events and classes, date online, and go out with friends. Also, you need to be open to love, and not run away from it because you’re scared or for any other reason. Lastly, love will come, but don’t rush it. Focus on your life as you stay on the lookout.