11 Red Flags When Dating in Your 50s to Look Out For

If you’ve made it to your 50s, the chances are high that you’re pretty dang wise when it comes to life. However, the chances may also be high that you haven’t dated in a long time. Maybe your spouse just passed, you’ve been focusing on your career, or you’ve just enjoyed spending time alone. Or maybe you have been dating but you’re wondering how things might change as you start to date into your 50s.

While we have an entire section of our website dedicated to senior dating advice, we want to focus in on something in particular today—red flags when you’re dating in your 50s.

What are the things you should be on the lookout for? What red flags can signal that your partner isn’t who they say they are or doesn’t have your best interest at heart? How do you avoid any common online dating scams?

If these are concerns you have, they’re valid. But rest assured, we’re here to help! Let’s take a look at the most important and significant dating red flags for singles in their 50s.

old Man on a train

1. Your romantic interest seems too good to be true.

This is the one we commonly refer to as “the sniff test.” Whether you’re dating in your 50s or really at any age, if the person you’re talking to seems too good to be true, there’s a good chance they might be.

Yes, we want you to meet amazing, attractive, and exciting singles. And yes, these people actually do exist! However, if they start to seem too good to be true, be on guard. It doesn’t mean you immediately need to stop speaking with them, but it does mean you should start to pay attention and be a bit more protective.

Some of the things to look for include:

  • They ALWAYS have the right answer to everything.
  • They change their answers or views on things to match with you.
  • They’re much younger than you and you’re not sure why they’re dating someone older.
  • Your gut tells you something is wrong.

2. They have reasons they can’t video chat with you.

As many older singles are turning to online dating to find love (and for good reason), this does raise a new list of concerns to be on the lookout for. One of the biggest red flags for singles dating in their 50s is if their online match isn’t able to video chat with them.

Video chat is an incredible way to verify that the person you’re talking to is at least the person you’re seeing in pictures. It doesn’t necessarily validate their claims, but it does validate they’re not some random person from halfway around the world who looks nothing like your match.

If your match tells you that for one reason or the other, they can’t video chat, this is a big red flag. Now, if they just can’t video chat today but they can tomorrow, that’s fine. However, if they have an excuse as to why they won’t be able to video chat for weeks or months, that’s a red flag.

Some of the common excuses you might hear include:

  • They’re working a job where they don’t have good enough service to make a video call.
  • They aren’t great with technology and can’t figure it out.
  • Their phone or computer is broken so they can’t make a video call.

3. They work as an offshore oil worker or some sort of international agent.

Piggybacking on the last red flag for dating in your 50s is if your match says they work as an offshore oil worker or some other form of international employee. Now, we’re not saying that every single person in the oil industry or working internationally is a scammer. However, this is by and far one of the most popular online dating scams we’re seeing these days.

The reason they claim to be an offshore worker is that they won’t be able to video chat because they’re offshore. Additionally, you can expect them to have some sort of money troubles with their family, kids, or to get a ticket to come see you. They’ll promise that as soon as they get back home, they’ll video chat with you.

When this happens, it is almost always a scam and is therefore one of the biggest red flags to look out for.

4. They bring up financial needs or concerns far too early (and ask you to help).

Here is a good rule of thumb—if your date asks you for money or starts talking about having money troubles that you can help them with, it’s a major red flag. Yes, some people in their 50s who are genuine people are going to have money troubles, and that’s okay.

However, when they start bringing those up too early (before you meet in person several times) or they start asking you to help, that is a major, major, major red flag.

Scammers like to target singles in their 50s and older because they know there’s a higher chance you’ll be vulnerable and may be sensitive to their concerns. If you’ve just lost a spouse or have been lonely for a while, they’ll get you to like them and then ask for money.

This should not scare you away from dating in your 50s, but it just needs to be something on your mind. If they ask you for financial help of any kind, it’s going to be a big red flag. And this hopefully goes without saying—don’t send them any money.

5. Your date is stuck in another age bracket than you (emotionally speaking).

Not all red flags when dating in your 50s have to do with scammers and fake people. Sometimes you can find red flags that just signal they’re not the right person for you, even though they are genuine.

Here’s the first one of those. If the single man or woman you’re talking to is living “a different age than their age,” that could be a red flag. For example, if you’re living a calm and established life but the man or woman you’re talking to is running around partying like they’re 25, that could be a red flag. This will all depend on what you’re comfortable with and what you’re ideally looking for.

6. They’re not fully over the baggage in their life, at least to a healthy point.

There is absolutely nothing wrong with having baggage, especially for singles dating in their 50s. You’ve lived a lot of life so there are bound to be things that have happened that weigh on you. But those things have also worked to make you who you are.

Here’s what we’re looking at though. Is the person still emotionally somewhere else? Are they in an emotionally healthy enough spot to carry on a new relationship? If not, that’s a big red flag. Even if you feel for them and their pain, it’s not going to be a healthy romantic relationship to get into.

For example, if their spouse just passed a few weeks ago, the chances are high that they still need some time to process that internally before starting to date.

How will you know? Well, if in the first few conversations you have with them, all they can talk about is something from the past, that could be a hint. If they mention it, that’s okay. And if you ask questions and they answer, that’s also okay. But if it’s all they can talk about and it seems like it’s all that’s on their mind, that’s your red flag.

7. Your match comes on WAY too strong too quickly.

While this is a red flag in dating at any age, it’s especially a red flag for dating in your 50s. If your new match comes on way too strong right out of the gate, that can be another sign of issues with baggage.

Yes, it’s exciting when you meet someone you like a lot! However, if it seems like they’re going from 0 to 100 in just a few dates, that’s a red flag. It can show they’re more concerned about filling a void in their life with someone¸ and less concern about who that someone is.

Remember, a relationship partner is meant to complement your life, not fill a hole.

This can also be a sign of emotional immaturity that you may not want to be a part of. Yes, people in their 50s can absolutely still be emotionally immature.

8. They make you act in a way you’re not comfortable with.

Remember the old cliché, you are who your friends are? Well, that goes a whole step further when you’re talking about the person you are dating. If someone brings out the best in you, amazing! However, if you start to date someone (even later in life) that starts to make you act in ways you don’t like, that can be a problem.

For example, maybe they like to engage in risky behavior? Maybe they like to swear a lot? Maybe they like telling dirty jokes? If these are things you enjoy or don’t bother you, no worries. However, if they are things that bother you and then you find yourself starting to do them, that’s a slippery slope and a major red flag.

9. They drink, smoke, or do drugs more than you’re comfortable with.

People live different lives. Some people love to drink, some love to smoke, and some enjoy doing drugs. While we aren’t here to debate the merits of these things, we do want to say this. If you’re dating in your 50s and you meet someone who does one or multiple of these things and you don’t like it, that’s a red flag.

No, it doesn’t mean they are a bad person. But it does mean they’re not the right person for you. Remember, red flags for singles over 50 don’t just have to be about bad things; they can be indicators that you’re not a great fit for each other.

10. They don’t treat others with respect.

This one is a simple one, but one worth mentioning. If they don’t treat you with respect, that’s a big red flag. If they don’t treat their friends or family with respect, also a big negative. Also, if they don’t treat people they don’t know with respect (like waiters, waitresses, bartenders, taxi drivers, etc.), run for the hills.

11. Any other dating red flags from any other age bracket.

The last thing we want to put on this list is that any other red flag from any other age bracket is most likely applicable for singles over the age of 50. For example, if they lie to you—red flag. If they refuse to compromise on something important to you—red flag. The list is pretty endless, but hopefully, you get the idea.

The Bottom Line

If you see one of these red flags for 50 year olds, should you immediately stop talking to the person you’re interested in? It depends. If it’s something that could affect your safety or your money like where you think they are a scammer, then yes, you should stop talking to them.

If it’s something like they’re rude to one waiter, that doesn’t necessarily mean you should cut them off completely. But if you start to see a pattern emerge, that’s where the red flag gets way more serious.

Overall, though, dating in your 50s should be exciting and can be very fruitful! Just make sure you’re on guard for these red flags so you can choose to avoid a situation that isn’t ideal for you. And if you do see a situation that’s not great for you, have the courage to look for someone else.

Photo of author

Author: Matt Seymour, MSF

Matthew J. Seymour is a dating industry expert with over a decade of experience coaching singles, reviewing dating apps, and analyzing trends within the industry. Matt is a published author with his most recent work “Get More Dates: How to Master Online Dating Apps” that hit shelves in 2023. With a Masters of Science in Finance (MSF) degree from the University of Florida and extensive knowledge of the innerworkings of the online dating industry, Matt frequently serves in an advisory role to some of the largest dating apps on the market. In Matt’s current role with Healthy Framework, he leads the interview team that regularly interviews key dating industry leaders, and leverages his financial knowledge and dating app experience to review and share what singles need to know to get the most out of dating online.