15 Biggest Red Flags When Dating In Your 50s – Watch Out!

A guide to date safely in your 50s

Dating experience | | , Journalist & Writer
Updated On: August 30, 2024
Red flags when dating in your 50s
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Are you 50 or above and looking for someone special in today’s ‘love at first swipe’ culture? Or simply waiting and hoping to find a partner with whom you feel ‘this is it’? Well, we all want our ‘happily ever after.’ But finding love at 50 and beyond can be scary and intimidating. Be it the awkward feeling that people your age are already off the market or the fact that the other person carries the emotional baggage of a previous spouse or multiple failed relationships, dating is a tricky track to navigate in your 50s. So, to simplify the process of mature dating, learn to identify the red flags when dating in your 50s before saying “I love you”. 

Unfortunately, in the overwhelming dating world these days, many accept the glaring red flags in women and men on dating sites as part of the package instead of viewing them as warning signs of an incompatible partner. We have jotted down some glaring dating red flags for those in their 50s:

What Are Dating Red Flags?

Casie, a 52-year-old divorced mother of two from Wisconsin, who has been struggling to find success in her second innings in the dating game, says, “Dating as an older woman can be challenging. I met someone on a dating app, and our first date started off on a perfect note: a romantic restaurant, perfect background music, and good food. But he went on talking about himself and describing all of his exes as ‘crazy’ while ignoring important conversations, i.e., stuff about us. That was the first and last time I met him.” So, what are some similar warning signs that qualify as dating red flags? Let’s take a look:

  • The person you are dating is self-centered and does not care about your opinion
  • They are dwelling in the past while carrying the baggage of all their exes, which reflects a lack of emotional maturity
  • They’re overly critical of every little thing you do
  • They blame you for everything
  • They avoid difficult discussions, which will eventually result in a lack of healthy, open communication

To get a better idea, take it from the folks on Reddit who opened up about the dating red flags they ignored. A Reddit user wrote: “Missed opportunities to bond. It sounds silly, but it definitely adds up to show how much they don’t care. It can be as simple as you driving and you say ‘Oh look! A rainbow’ and they don’t even care to turn their head.” 

Another user commented, “Isolating you from your friends and family. It took me a very long time to realize this. Narcissists are notorious for this. They get you believing that if people in your life are against your partner, then they’re against you as well.”

Related Reading: 9 Silent Red Flags In A Relationship No One Talks About

15 Biggest Red Flags When Dating In Your 50s – Your Cue To Run!

How to date in your 50s, you ask? Well, there is no denying that dating at fifty or beyond is different. You are older and wiser. You know people and their traits. But let’s admit, love can make you turn a blind eye to their flaws. Recognizing the red flags in women and men, when you’re dating beyond 50, is key to finding the right person. To help you with that, we have made a checklist of the 15 biggest but most common red flags when dating in your 50s. So, if any of these pops up, take a step back.

1. They have online dating profiles but no personal details

One of the red flags when dating in your 50s is when you find no personal details about the other person. While this may happen if someone is not well-versed with social media and dating apps, or prefers keeping their personal information under wraps, this lack of transparency amounts to red flags in men and women if:

  • They only use blurry photos of themselves
  • Refuse to share details about themselves even after you match and start talking 
  • They deny meeting in person

These are some of the major red flags of online dating. If a person is genuinely looking for someone, they will present themselves in the best way possible and not hide behind a shady profile.

Related Reading: 11 Dating Sites And Apps For Widows – 2022 Updated

2. They can’t stop talking about themselves

Talking only about what they enjoy or care about, without wanting to know what you want, is a red flag, whether you’re dating as an older woman or man. If you are meeting up at a place of their choice, doing what they like, please remember, some things never change. And it’s likely that, if you take things forward, they will continue to be equally self-absorbed. And your opinion will never matter to them.

single women over 50
Watch out for warning signs when dating in your 50s

3. They have never been in a serious relationship

If a person has been single for decades, it does raise curiosity about their commitment. The lack of serious relationships can indicate that there is a problem here. Hence, it is important to proceed with caution when the other person is carrying the ‘50 and never married red flag’.

Jennifer, a 57-year-old teacher from Texas, shared her experience saying, “Dating after 50 is not easy. I re-entered the dating scene in my early 50s as a divorced person, and one of the biggest surprises was that a huge number of men my age had not been in a long-term relationship. Of course, not having committed before 50 does not mean a man will never commit. But if he has never had a serious relationship by that age, it does alarm you.”

Related Reading: 9 Expert Tips To Know If Your Partner Is Lying About Cheating

4. They ignore difficult discussions 

An inability to have difficult conversations is fishy, especially if you’re dating over 50 because it indicates a lack of emotional maturity. People who cannot respect diverging opinions and walk away from arguments without hearing the other person out lack the ability to build lasting long-term relationships. This is a strong sign that you should take a step back and reassess their suitability as a partner before you become too emotionally invested.

5. They trash-talk about their past relationships

What does it mean if a person talks about their ex (or exes) all the time and it’s all negative? Well, there is no harm in being open about the past, but if they are over-critical and keep trash-talking about their ex/es constantly, it’s a glaring red flag telling you to not date them. 

Unresolved issues of the past can affect your present. Besides, if they can’t hold themselves responsible for their part in past relationships, there is no guarantee they will be accountable in the future. You need to think long and hard before dating someone with emotional baggage.

Our reader, 55-year-old Whitney from New York, had a similar predicament. She says, “I met a person who had had a recent breakup and was seeking a new relationship. We went on a couple of dates, but I realized he still had unresolved feelings about his ex that could’ve later proved to be a hot mess. Now, this is one of the red flags in men that I run away from. So, I moved on while treating it as one of the hazards when dating above 50.”

Related Reading: 12 Signs Your Past Relationships Are Affecting Your Present Relationship

6. They just want to get physical

Do relationships escalate to sex faster when you are older? They can, but it all depends on the two of you. Someone who wants to know you genuinely will not discuss sex on the first date or cancel plans when you just want to catch up for a coffee. If sex is all they want, without healthy communication or quality time, it’s a warning sign. Being physical is part of a relationship, but it’s not a great sign if it comes up early on. This is also one of the glaring red flags in men (when they try to convince women to have sex early on in the relationship).

dating over 50
Dating in your 50s can be tricky

7. They engage in love-bombing

There is a dialogue in the series Money Heist, where Raquel Murillo details how her ex-husband became abusive toward her. She says, “Toxic relationships don’t begin with abuse. If it were like that, no one would be in a relationship with someone who is abusive. In fact, it’s all the opposite. In the beginning, you fall in love with someone charming, intelligent, who makes you feel like the center of the universe.”

This is what love bombing looks like. Watch out for these signs:

  • They’ve said “I love you” too soon 
  • They want to be exclusive after 3 dates 
  • Paying compliments all the time
  • They’re showering you with an intense display of affection

These are all signs of an unhealthy dynamic. Being loved is a beautiful feeling, but getting love-bombed is emotional abuse.

Related Reading: 15 Early Signs He Is A Player And Isn’t Serious About You 

8. They have controlling behavior

A need for control is one of the worst kinds of red flags in dating. The person you’re dating may be afflicted with unhealthy jealousy or overpowering insecurity but they will not come out and say it. Instead, these niggling emotions push them to control every aspect of your life. When the need for control soars, the quality of the connection you share with them deteriorates. You may wish to reconsider getting into a relationship if your date displays unhealthy jealousy and controlling behavior.

Our reader, 56-year-old businessman Jeremy from Chicago, wrote to us: “My 52-year-old date Cathy appeared to be a fine woman, till about a month into dating. Soon, she wanted to know all about my movements and tried to control my decisions. After a couple of months, I realized it’s time to move on ​​because nobody wants to be in such a relationship, especially when you hit your 50s.”

9. They belittle you with offensive humor

Humor brings people closer. But there is a thin line between being funny and being offensive. A red flag when you’re dating in your 50s as a woman or a man, is when your date mocks you or belittles you. A person who likes you will respect you and will not put you down. This is an example of emotional abuse that can also affect your self-esteem and well-being in the long run.

Related Reading: 13 Signs Of A Controlling Woman

10. They are disrespectful toward others

At 50, you certainly don’t want someone who has not learned how to behave with others and feels it’s their right to be rude. It projects their lack of empathy. So, better get out of that relationship as fast as you can if you notice:

  • They’re rude to waiters
  • They pick fights with people around them
  • They foul-mouth their friends and family

11. They never apologize

Everyone makes mistakes. But if you’re dating someone who finds it hard to apologize and not take ownership of their actions, it is a red flag that you should not ignore. Saying “sorry” shows that the person is capable of taking responsibility and accountability for their actions in the relationship

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Have you faced any issues while dating in your 50s?

12. They are frequent liars

Now, they may just tell you white lies or small lies. But catching them constantly lying to you is a glaring signal that you should let them go out of your life. Any kind of dishonesty is an act of disrespect in the relationship. You should seek out people whom you can trust. 

13. They lack financial planning

Financial stability and responsibility are important factors to consider while dating in your 50s as a woman or a man. Many assume that talking about money is unromantic. Yes, it might be odd to ‘talk money’ in the early stages of dating, but if you’re considering a future together, you need to know if:

  • They have a habit of spending impulsively
  • They’re in debt
  • They have any long-term savings at all

For a healthy relationship, transparency is the key. If they have no clarity regarding their financial goals, it is a potential red flag.

Related Reading: 10 Critical Emotional Needs In A Relationship

14. They don’t prioritize your children’s emotional needs

Getting back into the dating pool, be it after your divorce or your former spouse’s death, is not easy. The truth is: it’s tough dating in 50s as a woman or a man. Even more so if you are a parent because no matter how old your children get, they always need you in some capacity or the other. If you find yourself with a person who wants you to prioritize them over your children and their needs in all situations, you may want to rethink your decision to get into a relationship with them. 

15. They are emotionally unavailable

Dating at fifty is hard anyway. On top of that, if someone is emotionally unavailable or is withholding affection, it can get doubly hard. You might end up feeling emotionally abandoned, with your intimate life being affected. The whole point of being in a relationship is to be there for each other. So, if they can’t be there for you emotionally, what’s the point of dating?

How To Navigate The Dating World Safely In Your 50s

Age is just a number, they say. But is it so, when it comes to dating? Well, senior dating sites where you can meet singles over 50 will have you believe that age isn’t really a barrier when you set out to date someone. But finding love at 50 can be a challenging task because of the simple fact that you’re more vulnerable. Your loneliness may make you trust someone early on in the relationship, and that can be harmful for you in the long run. But don’t fret. We have listed a few tips to help you navigate the dating world safely in your 50s:

1. Research before you take the plunge

It’s extremely important for you to research your date before you decide to take things forward. Though this rule applies to dating in general, if you’re dating at 50 or beyond, you’ve got to be doubly aware of dating scams, as older people are more vulnerable to such crimes. You should be aware of:

  • Financial scams: Romance scammers target senior dating apps, as older people who are dating after 50 aren’t too tech-savvy. Avoid sharing financial information such as bank details and OTPs
  • Catfishing: Beware of prospective dates with flashy profile photos and bios that are too good to be true. You may end up dating a catfish who’s good at creating a fake image online
  • Fake sites: If you’re dating online to meet singles over 50, choose a site that’s genuine and has good reviews

Related Reading: 5 Reasons To Research Your Online Date Before You Meet

2. Inform a third party about your date and your whereabouts

Now, this is especially for single women over 50. Whether your date sounds fishy or not, it’s always a good idea to share your whereabouts and the basic details of your date with a trusted friend or family member if you’re meeting your date somewhere. Make sure you share:

  • Your date’s photo
  • Your date’s phone number and social media handles
  • Your location details 
More on unhealthy relationship

3. Ask them questions

This is important if you’ve just started talking to someone. Now, your date may not be an axe murder but just a shy person. But for the sake of your mental peace, ask them questions to help you know them better. And note which questions they avoid. You can ask them:

  • Where they stay
  • What sort of job they do
  • About their family
  • About their past relationships 

Related Reading: What To Do When You Realize Your Relationship Is A Lie

4. Avoid sending nudes or sexting initially

This is a crucial piece of advice, especially for single women over 50. Yes, we understand, you might be tempted to share some jazzy texts to spice things up a bit. But avoid sexting, or sending nudes or that picture of yours in next to nothing, if you’ve just started talking. You don’t wish to end up being blackmailed, after all. Sextortions are a reality. So, think twice before hitting ‘send’.

Debra, a 51-year-old banker, wrote to us, saying, “I was dating someone for a couple of weeks, and every time we texted, he would ask me for some intimate photos of mine. I almost sent him a photo of mine in my favorite lingerie, but then good sense prevailed and I didn’t. A few weeks later, he ghosted me randomly. Now that I look back on the incident, I wonder if he was just a sextortionist.”

5. Don’t tolerate disrespect

This goes for people of all ages and especially for those in their 50s. Disrespect is something you should not accept from your date. Go ahead and block or ghost the person online if they:

  • Don’t listen to your point of view or disregard your feelings
  • Talk down to you
  • Ridicule you in private or in public
  • Control you and your actions
  • Resort to verbal or physical abuse

Key Pointers

  • The basic dating rule of thumb is to identify the biggest red flags when dating in your 50s
  • To find potential partners, look for those who accept their mistakes and apologize, avoid individuals who trash-talk about their past relationships, and be cautious of the ’50 and never married red flag’ category
  • Having an idea about these red flags will safeguard you, because emotional well-being is crucial
  • If you spot a red flag, choose a non-confrontational approach to discuss your concerns
  • To counter the red flags in women and men on dating sites, research before taking the plunge, ask them questions, and avoid sending nudes initially

Final Thoughts

Red Flags of Dating In Your 50s
Red flags of dating in your 50s and safety tips to follow

The key to figuring out how to date in your 50s is to remember there is no age limit or expiry date when it comes to finding love. With the number of senior dating sites in the dating sphere, you have tons of options to choose from. Just keep the checklist mentioned above in mind before getting into mature dating. 

Explore the best options for senior dating. Look for tips on dating beyond 50. Check the dating guides that will help you explore the dating pool. Most importantly, don’t forget that you have the bonus of several years of experience. Use it to identify the red flags when dating in your 50s, and attract the right partner.

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