Diving Into the Dating Pool in Your 50s? Watch Out for These 13 Red Flags

The hit movie Sleepless in Seattle famously had a line that said, “It’s easier to be killed by a terrorist than it is to get married over the age of 40.” 

While it’s not true, it can feel so in the modern day when you consider finding love in your 50s. 

Whether you’re trying to dip your toe in the dating pool or ready to dive in, you should know the water now comes with all sorts of red flags. 

It’s best to be aware of them before getting soaking wet.

Why Bother Dating After 50?

Jennifer Lopez, aka JLo, was 52 when she married Ben Affleck.

Ok, so you’re not a megastar with a Hollywood physique, but you are pretty amazing. 

  • It’s good for you. Companionship and intimacy help prevent mental health issues and keep you active. Even having (gasp!) sex over the age of 50 is proven to help with memory, pelvic floor strengthening, and a lower risk of prostate cancer. 
  • It’s all about you. By 50, most people reach a shifting point in life where the kids are raised, and retirement is on the horizon. You have much more life experience and relationship knowledge that cuts down on bad dates and wasted time. 
  • It’s an adventure for you. You might be stuck in ruts and routines that could use some shaking up after the big 50th birthday celebration. Dating is different in your 50s, but it’s still an adventure.

13 Red Flags When Dating in Your 50s

There is a world of research about the benefits of dating in your 50s, but there are more red flags (meaning warning signs) than ever before. 

1. They Are Vain and Shallow in Dating Profiles

Call it a red flag or a dodged bullet, but many people on dating apps (and 33% of people over 50 are) will weed themselves out with shallow posts about their dealbreakers and demands.

If weight, attractiveness, or socio-economic drivers are mentioned as a mold for their perfect partner, they are likely never to be happy. Swipe left. 

Sure, we all wish we could be George Clooney or JLo after 50, but that’s not realistic or respectful. 

2. They Have Never Been in a Committed Relationship

Love can bloom later in life, but look out for the 50 and never married red flag. While there could be legitimate reasons this person never got hitched, there could also be an unexplored world of mental, emotional, or attachment issues you don’t want to dive into. 

It becomes a brighter shade of red with flashing lights and fog horn if the person has never been in a committed long-term relationship. Either they don’t want one or can’t sustain one, and neither bodes well for your future happiness. 

3. They Won’t Meet in Person

People dating over 50 have adjusted to the life of texting and DMs, either begrudgingly or excitedly. But at some point, two people need to meet in person to have a genuine connection and explore what’s possible. 

sweet couple watching the sunset red flags when dating in your 50s

If a potential partner checks all the boxes but keeps dodging or delaying meeting in person, they might have commitment issues. 

On a much more serious level, they could also be a scammer or catfish, trying to get your money or use you as a nice escape from their boring life. Ideally, limit how long you’ll send messages before you insist on meeting in person or walking away. 

4. They Play Dodgeball with Personal Details

This person doesn’t want to share a single thing about themselves but will dig into your closet and start pulling out skeletons. Even if they are a great conversationalist, they still aren’t forming a two-way connection.

Narcissists can use this tactic to learn information about you and then mirror your interest to lure you in.

Other profile predators could be trying to find a side piece from their marriage. Even if they are totally legit, it’s concerning when someone won’t open up about their favorite childhood memories or what type of food they want to eat.

If you only wanted to talk about yourself, you could do that without dating. 

5. They Only Talk About Themselves 

On the flip side, there are those who can’t stop talking about themselves enough for you to order your own coffee choice. You played basketball?

So did they. Only better. And longer. And with a celebrity. Twice. Their attempt to impress you will make you cry foul. 

This problem also manifests in your dates. Do you always go where he wants to go? Does she always get to pick the movie? Relationships are as much a compromise in your 50s as they were in your 20s. Some things never change. 

6. They Drink or Take Pills to Excess

Buying (and being able to afford) fancy drinks in your 50s is a luxury, but if your date is making Moscow Mules more like a shot or getting sloppy drunk at your winery tour, there might be an unaddressed addiction there. 

There’s also no shame in taking medication to help with mental health issues, but if you notice constant popping of pills or some missing from your home, it’s time to run away from the red flag. 

By the time you’re dating in your 50s as a man or a woman, you’ll likely run into people who admit to recovering from an addiction. While it’s not a red flag, it is a moment of pause. Are you okay with not having alcohol in the house?

Do you feel comfortable attending meetings when invited? 

7. They Won’t Bend on Their Own Beliefs

People in the 50s dating range are Gen X, on top of having life experience. You grew up tough and independent, having the courage of your convictions.

At 50 and beyond, you aren’t likely going to explore a new religion or start being an adrenaline junkie. 

They might also feel differently about modern topics like gender fluidity and the Me Too Movement. This could set a stage for golden years turning brass with fighting and mismatched beliefs. 

8. They Don’t Take Care of Themselves

Aging is hard on everyone (except George Clooney and JLo), so it’s okay to stop trying to look perfect all the time or not learn the 100-step process to contour your face. However, brushing teeth and bathing shouldn’t be up for debate. 

mature couple on a date red flags when dating in your 50s

Wearing dirty clothes or having a home full of clutter is now a lifestyle choice, and you’ll be cleaning up the mess for years to come if you don’t heed the warning sign. 

9. Their Finances are Messy

People aren’t too big to fail, so some people could be dating simply looking for another nest egg painted with feigned emotions or looking for desperate people to support their lifestyle.

Lack of financial planning is also indicative of impulsive activity or self-control issues. 

You can also enter a committed relationship with separate bank accounts, but if the other person has gone this long hoping their last check bounces, you’re in for a financial roller coaster if you don’t get off the ride. 

10. They Bring the Drama

We’ve got a lot of baggage to unpack in our 50s, so kids and exes come with the territory. However, a narcissistic ex is going to make your life hell. Kids who don’t accept you will ruin every family and holiday gathering. 

A weak partner who can’t set boundaries with the ex or kids will be a victim of every run-in, and you’ll be the bad guy (or girl). 

You can get a sneak peek of this by looking through their social media feeds (it’s okay, everyone does it) to see if the kids or ex are commenting or snarky on every post. 

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11. They Have a Personality Disorder like Narcissism

The difference between a self-absorbed person and a narcissist is that the narcissist wants to control, manipulate, and submit you to their will.

A narcissist stands out by love bombing you with overwhelming affection and presents at the start, only to start tearing you down and eventually abandoning you before starting the cycle all over again. 

If you are a people pleaser or an empath by nature, narcissists will be attracted to you, and you will go to them like a fly to honey. Beware if you are one of these people. You tend to seek out the people who need fixing, not the nice people. 

12. They Want Commitment… NOW

Beware of anyone who is in a rush to commit. It can signal attachment issues or simply trying to have someone (anyone) fill the gap in their life for events and vacations. 

You will not feel special and rush in so quickly that you never truly get to know each other, increasing the risk for a divorce, and then you’ll be Googling “Dating at 65.” 

If you feel pressure to be in a commitment now, use that strong voice you’ve developed over a life well lived and stomp on the brakes. If you get backlash, speed away in the other direction. 

13. They Are a Fool Rushing In

When we’ve experienced relationship trauma or a bad breakup, the old adage of “get over someone by getting under someone else” doesn’t really work in your 50s (nor did it in your 30s, but who’s counting?).

This red flag comes out quickly, but you’ll often have to be perceptive to notice it. 

Someone telling you they got out of a 10-year marriage a month ago but gives you the  “really over it” promise, they certainly are not over it. They are avoiding the pain and heartbreak. 

What are Some Good Rules for Dating After 50?

Well, all that makes it sound like dating in your 50s is a nightmare, right? It’s not. You just have enough information to know what to avoid.

Now, here’s how to approach it from a healthy perspective. 

1. Don’t Be Pressured

Your kids or friends might be pressuring you to “get with the times” and sign up for dating apps or could even start a “Find My Mom a Date” TikTok account.

You control when you jump into this dating pool, and you shouldn’t be pressured to get out there if you’re not ready. 

2. Be Flirty Like You’re 30

There’s no age limit on flirting. You can still woo and wow a potential partner at the grocery store, gym, or (gasp!) church.

Even if it is fruitless, just trying out your flirting skills will help you explore the side of you that needs to feel sexy and has been hidden away too long. 

3. Set Sex Standards

While the fear of pregnancy is gone, the risk of STDs is still there. Menopause, erectile issues, sex drive, body issues, dryness, kinks, icks—talk about it all.

mature couple staring at each others eyes red flags when dating in your 50s

There’s a lot to unpack. Dating in your 50s as a woman is like having an entirely different body after menopause. 

4. Don’t People Please

People pleasers are more likely to be scammed or hit up for money by their suitors. Especially in today’s entrepreneurial age, you’ll find more people looking for startup money or a “retirement plan” idea.

You’ve taken care of enough people. Take care of yourself and share that through compassion, not cash. 

5. Set Realistic Expectations for You and Them

The Notebook will forever give us an unattainable target for love in our older years. Be realistic about what you can and want to give a relationship and what you should expect in return.

Gone are the days when you feel the need to impress everyone. Just enjoy every second, and laugh through the missteps. 

6. Embrace this Stage of Dating Life

When you were 18, you wanted to be 21. When you were 30, you missed being 21. When you were 40, you would’ve killed to be 30 again.

Stop time-warping and just enjoy the wrinkles formed from laughing memories and the love handles from those family pizza nights. Be present before you’re 70, wishing you were 50 again.

What Is the Biggest Red Flag in Dating a 50+ Man?

If you’re dating a man in his 50s or beyond, a huge red flag is that he is looking for a replacement for his wife, who either left or passed on. 

He might have liked how his wife cared for him and got used to the habits and family rituals.

Maybe he is still grieving a wife who recently died and wants comfort but isn’t ready for a relationship.

If he constantly compares you to her and tries to get you to act like her, that’s a huge red flag. You can cater to his needs but on your terms and timeline.

What Is the Biggest Red Flag in Dating a 50+ Woman?

Extreme demands are the biggest red flags when scouting women in the 50+ dating world. She might be fiercely independent and not let a man so much as open a door for her.

Or she’s so needy you have to go to the bathroom with the door open so she can be close to you.  

These issues are rooted in low self-esteem, fear of abandonment, or trauma. She might be a catch, but she needs some mental health support first. 


Dating over 50 can be fun. You each have more stories to tell and have learned a lot from the mistakes you’ve made and seen others make. 

Because of those lessons, you are a better companion, and you’ve got another couple of decades of life expectancy to enjoy with someone else.