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The 10 Major Red Flags When Dating in Your 50s and Beyond!

Starting to see red flags when dating in their 50s

There are plenty of red flags when dating in your 50s to be mindful of so that you don’t get scammed, used, abused, and end up with your heart broken. Dating in your 50s can be daunting, especially if you’re newly single and haven’t been on the dating scene in years (or maybe decades). Technology plays a huge part in how people meet today, and although it has made it much easier to connect, it has brought with it a lot of potential risks, especially for older and more vulnerable people.

Aside from online dating scams, there are other red flags when dating in your 50s to be on the lookout for. Now that you’re older, it’s likely you’re more set in your ways, clear about what you want (and don’t want), and you potentially have some other factors to consider including kids, health issues, finances, and retirement plans to name a few. All of these factors can make it even tougher to meet the right person.

It’s natural to want to find someone to share your life with. Someone to sip coffee with, in the morning, go for a walk on the beach, snuggle up on the sofa and watch a movie, take the dog to the park, try dinner at that new Indian restaurant, go on a Caribbean cruise this summer, and spend the holidays with. But this desire to meet someone special should not blind you to overlooking the many red flags that may present themselves during the dating process.  When you know what to look out for you can prevent yourself from being scammed, protect your heart from unnecessary heartbreak, notice when someone is using you or is not right for you, save yourself time, and find your way to someone who is compatible with you and the life you want to live in the long run.

There are many red flags to look out for when dating in your 50s, But the 10 main ones are:

  1. Red Flag 1: Dubious online dating profiles
  2. Red Flag 2: Always has a reason not to meet face-to-face
  3. Red Flag 3: Avoids sharing basic information with you
  4. Red Flag 4: Moving too fast
  5. Red Flag 5: You are not compatible
  6. Red Flag 6: Mentioning their ex on the first date
  7. Red Flag 7: They lie to you
  8. Red Flag 8: They don’t respect your boundaries
  9. Red Flag 9: They are not independent
  10. Red Flag 10: They are flaky

In this article, we’ll explore these dating at 50 red flags in more detail to clarify what’s normal (and what’s not) so you know if you’re overreacting or justified to be concerned.

Red Flags to Look Out for In Your 50s

Red Flag 1: Dubious online dating profiles

I’m starting off the dating at 50 red flags with sketchy online dating profiles and behavior that is native to scam artists. Why? Because the older you are, the more vulnerable you are, and the easier of a target you become in the online dating world.

So, what should you keep an eye out for?

  • Online dating profiles with little to no information - usually this is because they have something to hide (e.g. they’re married, or pretending to be someone else). Who joins an online dating site with the genuine intention of meeting someone, but chooses to not post any photos or basic details about themselves?
  • Crummy grammar - Scam artists will often use poor grammar on purpose, like “you handsome man.” Most people would immediately delete or ignore a message like that and consider it spam. So anyone who responds is branded an easy target.
  • Photos that are too good to be true -  If a young, beautiful, single woman messages you out of the blue and has stunning profile pictures posted of herself online, don’t get carried away. It’s unlikely that someone much younger than you would be looking to date someone significantly older without reasons other than love. If something feels a little sketchy and you’re not sure whether she is who she says she is, do a reverse image search using Google Images to see if the images come up as a stock image or someone else’s photos.

Remember, this is the internet we’re talking about. People are not always who they say they are. And you are right not to immediately trust anyone until you have spent enough time with them and they have proven their trustworthiness to you over time.

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Red Flag 2: Always has a reason not to meet face-to-face

This is one of the red flags when dating in your 50s, or any other age. There are a couple of reasons why someone may pile on the excuses so that they avoid meeting you face to face. The first is that they are not who they say they are (and are probably catfishing or scamming you). The second is that they want to have the mental or emotional aspect of a relationship without the commitment of physically being there in person. Often this is because they are already in a relationship, or they have no intention of committing to anyone and just enjoy being able to reel someone in.

So, how do you get around this red flag? As a general rule, I wouldn’t spend more than a couple of weeks talking to someone online before meeting up face-to-face, or at least having a video call. This ensures that you don’t get too emotionally invested in someone too soon. Plus, meeting face to face is necessary to gauge whether you have a genuine connection and the chance at something long-term. There’s only so much you can go on from text messages and phone calls.

If you’ve suggested meeting up a few times and they avoid answering, make plans then reschedule or cancel last minute, you’re right to be suspicious. The first time someone cancels, you can give them the benefit of the doubt, but the second time is a definite red flag and your cue to move on.

Red Flag 3: Avoids sharing basic information with you

Keeping secrets from her partner

If someone is interested in meeting new people, forming connections, and is open to falling in love, they will be excited to learn more about you and have you learn more about them. Naturally, you don’t want to share the nitty-gritty details like how many sexual partners you’ve had or your current credit rating on date number one. But in order to get to know each other better, you have to be willing to open up and share.

So another of the red flags when dating in your 50s is if someone refuses to share even the most basic information with you like their age, what they do for work, their last name, when their previous relationship was, etc. Asking questions like these is not crossing a boundary, so if you’re met with defensiveness or a lack of response, it’s probably because they are hiding something or severely lacking in social skills.

If someone is not sharing anything with you, then don’t be the one to give up personal information about yourself. If they are digging into your personal life and past, be very wary. This is a classic narcissist move. They will learn as much as they can about you to fake a connection and lure you in, then use everything they know against you.

Red Flag 4: Moving too fast

At the other end of the spectrum is someone who is trying to go way too fast too soon. They bombard you with texts and calls throughout the day. They start talking about sex or being sexually explicit before they even know what your boundaries are. Generally, they have a very needy vibe and it feels like they have nothing better to do than talk to or spend time with you. They have shown their jealous side at the mention of you dating other people or exes. Maybe they’ve already dropped the L-word or have declared that you are their soulmate, and you’ve only known each other for a few weeks.

Usually, this is a sign of someone who is looking to jump into a relationship to fill a void in their life (which we all know doesn’t work), or it’s a sign of emotional immaturity. You’d think that people in their 50s are too old for this, but you can still be immature no matter how old you are if you haven’t worked on dealing with your baggage, insecurities, and childhood wounds.

It can be exhilarating when you meet someone new you click with, and it feels like they just “get” you and are the person you’ve been searching for. But remember that it takes time to truly get to know someone. So, if you feel like things are going too fast, don’t ignore it, and don’t be afraid to say something and slow things down. If they don’t respect this and keep moving at the same pace, get out of there.

Red Flag 5: You are not compatible

Next up on the red flags when dating in your 50s to watch out for is incompatibility. This sounds like a no-brainer, but you’d be surprised how many people continue to date someone who is clearly not right for them, only to have everything blow up in their faces months or years later.

Compatibility does not mean that you share all the same interests and hobbies, enjoy the same food, wear similar clothes, and have the same dreams. It’s normal to have differences because you are two individuals. BUT, what does matter is that you share some interests, whether it’s going for walks together, enjoying the same kind of movies, or reading together on a Sunday morning. This means that you will have things that you can do together, aside from sex.

What’s also important is that you are aligned on the big things like religion, family values, commitment, whether you want to get married again, where you want to live, how you want to spend your retirement, how you manage money, etc. When couples are not aligned on these factors, it always leads to arguments, and in most cases, a breakup. So do yourself a favor and discuss these things sooner rather than later. You’ll save each other a lot of time and heartache.

Red Flag 6: Mentioning their ex on the first date

A classic red flag at any age is when you just started chatting with someone and they casually drop in their ex. You’re on a date with someone new and it’s fun and exciting and the energy should be positive and flirty. Mentioning the ex is a surefire way to kill the possibility of a new connection!

Occasionally you’ll go on a first or second date and the conversation will be flowing effortlessly and you’ll get quite deep without intending to. It will feel like you’ve known each other forever. In this case, you might ask about their previous relationship, and exes may be mentioned. This can be okay, as long as there’s no ex-bashing or blaming. If someone is still blaming their ex for something or seems angry, hurt, or upset about their last relationship, this is a sign they are not quite over it yet. Best to move on and avoid being a rebound.

But generally, the subject of exes shouldn’t come up until you’ve been on a handful of dates and are starting to build an emotional connection with each other. When dating in your 50s, it’s likely that one or both of you will have kids, and will therefore still be in close contact with your ex. This is normal and a part of the baggage I mentioned earlier when dating at this age. So it’s essential that neither of you are the jealous type, and that you’re okay with the ex still being in the picture.

Red Flag 7: They lie to you

Next on the list of red flags when dating in your 50s is if someone lies to you. This can be a small lie, like something they mentioned in their profile, or a massive lie, like saying they’re single when they’re actually still married. This is a common lie that people who are going through a separation or a divorce will tell, either because they want to pretend that their baggage does not exist, or they are already single in their mind, even if they aren’t on paper. Either way, it’s still a lie!

Even if someone tells a small lie, such as claiming they can play the piano on their profile, and then it turns out they can’t at all but would love to learn, take it seriously. If they’ve lied to you about this, what else are they lying about? You can learn a lot about someone’s toxicity levels by paying attention to how truthful they are.

Beginning on a lie is no way to build a strong relationship. There will always be that seed of doubt in your mind that questions everything they say and do. Are they really meeting Sally for drinks after work? Is that business trip really a business trip? Does she really like my Hawaiian shirt?

The best thing to do is to call out a lie straight away. Serial liars will try to cover themselves by telling another lie.

Red Flag 8: They don’t respect your boundaries

Disregarding her partner's boundaries

One of the biggest dating at 50 red flags is when someone does not respect your boundaries. This can happen in a number of ways.

Maybe they call you frequently while you’re at work, even after you’ve mentioned that it’s not a convenient time for you to chat. Perhaps they insist on meeting you at your house before a date or walking back to your place after, when you’re not quite yet ready to share where you live. Maybe you even feel a little pressured to do something you don’t yet want to do, like go on a road trip together, or meet family and friends.

When you’re getting to know someone, it’s normal for minor conflicts like this to arise. The next step is to communicate your boundary, e.g. “I love talking to you, but when I’m at work I need all my focus and attention, so I’d love it if you called after work instead when it’s convenient for you. How does that sound?”

Once you’ve communicated your boundary, pay attention to whether it is respected or crossed. If someone knows your boundaries but continues to ignore or disrespect them, it’s a clear sign that they don’t respect you and want everything to happen their way. This is your cue to break things off and move on. And remember, you’ve got to respect other people’s boundaries too - everything on this list is a two-way street. Don’t expect more than you’re willing to give.

Red Flag 9: They are not independent

A red flag in women (and men) to watch out for is when someone does not have their own independence, and this can show up in different ways.

For example, if a woman is always able to meet you any time you suggest a date, even if it’s last minute, this creates the impression that she doesn’t really have anything else going on. Maybe she gets jealous or suspicious when you go out with your guy friends and always tries to persuade you to stay with her instead. This isn’t ever a good sign because a strong relationship requires both people to be thriving on their own, and maintain their own friendships and hobbies outside of each other.

Another sign of someone who lacks independence is if they still live with their parents, or have moved in with their children. Sometimes this can be temporary, if they’re looking after an ill parent, or helping a child with their newborn, and that’s fine. But a more permanent situation suggests a lack of independence and autonomy. Peak into the future and think about what it will be like going around to theirs and never being alone. Or worse, maybe when you take the next step to move in together, they’ll want their mother to live with you too!

Red Flag 10: They are flaky

Finally, number 10 on the red flags when dating in your 50s list is when someone is being flaky, or in other words, they aren’t really committing to you.

Maybe they take forever to reply to your texts (longer than a week is never acceptable unless someone has died). They say they’ll call you later but then they completely forget to. They cancel plans with you at the last minute. Or they avoid having any kind of deep or serious conversation, so your connection never progresses to anything more than surface level.

When someone behaves in a flaky way, it’s usually because they aren’t that interested in you, or they’re already in a relationship and have no intention of pursuing things with you. While it’s natural for someone to occasionally bail on plans, it shouldn’t happen more than once when you’re in the early stages of dating. If someone is willing to treat your time and feelings so carelessly, do you really want to continue to invest in them?

My advice is to give them one chance, and then call it a day and move on. There are plenty of amazing single people out there who will not flake out on plans with you and be respectful of your time.

These are some of the most common red flags to watch out for when dating in your 50s so that you avoid getting hurt, or worse, scammed, and increase your chances of finding love with someone who is compatible with you and the future you want to build. The most important thing to do when you notice a red flag is to remove yourself from the situation - don’t ignore it! You might consistently give your friends and family the benefit of the doubt, but a total stranger has not earned this privilege. Remember, if something feels wrong or too good to be true, it probably is. Trust your intuition and let it lead the way.

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