21 Things to Watch Out for when Dating after Age 50

Reentering the dating pool? Keep your eyes peeled for these red flags

Written by John Keegan | Edited by Dev Murphy

Last Updated: March 15, 2023 References

General Red Flags

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Online Dating Red Flags

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Red Flags When Dating Divorced People

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Red Flags When Dating Widows/Widowers

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Signs of Narcissism

Whether you’ve been dating around for a while or you’re newly single and ready to mingle, dating can be tricky, especially after a certain age. But it doesn’t have to be! There are a number of red flags to keep an eye out for when dating at 50 and beyond that’ll help ensure your time wading in the dating pool is a fun, flirty, and safe experience. We’ve listed all the red flags you need to know about below!

This article is based on an interview with our dating coach, John Keegan. Check out the full interview here.

Things You Should Know

Make sure your expectations align from the start. If you’re after a casual fling and they’re after The One, communicating this upfront will save you both time and heartache.
Be wary of dating profiles with limited personal info, and avoid giving people you meet on apps your personal contact info until you’re confident they’re on the up-and-up.
If you’re dating a widow/widower, note if they still seem to be in mourning. If they’re still actively grieving their late spouse, they may not be ready to date.
When going out with a divorced person, observe if they still seem hung up on their ex. Trash-talking, bitterness, and general mistrust of future relationships are red flags.

Section 1 of 5:

General Red Flags

1
They text too much. A little bit of texting here and there? Great. Texting to communicate plans? Wonderful. Good morning texts? Happy Monday texts? Let-me-pour-my-soul-out-to-you-in-the-middle-of-your-workday texts? If your date is texting you all the time, it can get real oppressive, real quick. It’s a sign they’re a bit too clingy, that they’re moving too fast, or maybe that they just have way too much time on their hands. Tell them gently to ease up, and if they don’t, it might be time to break things off.
2
They’re unreliable. One day you’re texting and making plans to hang out again…the next, they’re nowhere to be found! And when they do make dates with you, they're always during the work week, never the weekend—and they often get cancelled last-minute. If your date is a flake, just walk away: they’re not worth your time.^{[1]
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- If you’re hesitant to break things off just yet, or if you suspect their excuses for flaking are genuine, communicate that you’re frustrated by their inconsistent availability. If they try to improve, they might be worth another shot, but if not, well, there’s the door.
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3
They’re immature. Sure, you want someone who’s young at heart, but that doesn’t mean Peter Pan! Find a date who doesn’t exhibit signs that they haven’t quite grown up yet. At 50 (or older), you deserve someone as stable (financially and emotionally), grounded, and mature as you—and they definitely need to not treat you like their parent.^{[2]
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- If your date is still partying like they’re 22, it may be your cue to move on (unless, of course, you are also still partying like you’re 22, in which case, right on!).
4
You have mismatched expectations. This red flag doesn’t necessarily mean you or your date is in the wrong—just that you might not be right for each other. Even if you’re just out for a casual, short-lived fling, make sure you’re both on the same page about what you want and need from each other.
- Maybe your date just wants some company while you’re looking for some physical affection, or vice versa. Maybe they’re looking for The One, while you’re just out for some fun. Be upfront about your expectations from the get-go, and you could both avoid some frustration or heartache.
5
They go too fast, too soon. Going too fast too soon is a sign the person you’re dating is a little desperate or clingy, or maybe jealous. Maybe they just don’t know what they want, and instead of taking the time to figure it out, they’re rushing things with you. Worst-case scenario, going too fast could be a sign that they have some ulterior motives, like wanting to get in bed with you sooner. Don’t be afraid to go as slow as you want, and to let your date know if they’re rushing things.

Section 2 of 5:

Online Dating Red Flags

1
Their dating profile has limited information. You match with someone on Hinge or OK Cupid with a cute photo, a few funny one-liners in their bio…and that’s it. Now, dating profiles aren’t exactly the place to write your memoir, but if the person you’re considering dating doesn’t even have the basics—like age, education, general location—then there’s a chance they’re hiding something.^{[3]
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- They might be secretly married and trying to cheat on their partner, or they might be trying to scam you!
- If you’re concerned your match might be lying, copy their profile photo and reverse search it on Google images to see if it turns up anywhere else. You might find your match’s social media profiles or professional website, which might give you more info—or you may even realize they stole the photo from someone else!
2
They want to talk online, but not in real life. Some people just want a little company. There’s nothing strictly wrong with this, but if you meet someone online and the relationship doesn’t seem to be progressing beyond virtual communiques, it’s worth asking them where they see things heading. They may just want a pen pal—or they could be hiding something, like a real-life relationship.^{[4]
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They want to communicate off the dating site too soon. Dating apps and websites are pretty darn secure. If you match with someone who insists on taking things to email or text too soon, they could be trying to get your personal information and use it to scam you. Be wary! Only move the convo off the app when you’re confident they’re on the up-and-up.
- Online dating is a great way to meet new people, as long as you do it safely. Generally, try to avoid exchanging personal contact info until after you’ve met your match in person. When meeting them in person, meet in a public area, and let your friends know where you are.^{[5]
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  Trustworthy Source
  Rape, Abuse, and Incest National Network
  Largest anti-sexual assault organization in the US providing support and advocacy for survivors
  Go to source}
4
They ask for money. Nobody you meet on a dating app should be asking you for money, unless they’re like, a Nigerian Princess or someone authoritative like that. (We’re kidding! Do not give your money to someone claiming to be a Nigerian Princess.) If you match with someone on a dating site and they ask for money, don’t respond—just unmatch with them, and report their account to customer service.^{[6]
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Trustworthy Source
Rape, Abuse, and Incest National Network
Largest anti-sexual assault organization in the US providing support and advocacy for survivors
Go to source}
- Scammers can be sneaky, and they might not ask for money directly. Instead, they might give you the opportunity to invest in a promising new business venture…. No matter how promising it seems, just say no.

Section 3 of 5:

Red Flags When Dating Divorced People

1
They trash-talk their ex. Once you get to a certain age, a lot of people in the dating pool have had past relationships, maybe even marriages. Past relationships don’t define us, and they can enrich our lives and teach us a lot. But if you go out with a divorced person who’s constantly bad-mouthing their ex, it’s a sign they’re not over the relationship yet. What’s more, it can be pretty darn unpleasant to listen to someone complain all evening! You deserve someone who’s fully available to date, and not hung up on the past.^{[7]
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- Their ex could have done a number on them, and maybe it makes sense that they’re still hurting from that relationship. Regardless, you deserve to go out with someone who’s totally available—and not be someone’s rebound or source of free therapy.
2
They don’t take responsibility for their role in past relationships. It’s one thing to still be wounded by a past relationship. It’s quite another to refuse to acknowledge the part you played in those relationships! If it seems like all of your date’s exes were responsible for ruining the relationship, that’s a mondo red flag: it suggests they don’t take any responsibility for their behavior in relationships, or that maybe they expect way too much from their partners. Run!
3
They’re negative about relationships. Maybe your date seems to have moved on from their past relationships, but they don’t seem all that excited to see what the future has in store for you both, and frankly, they just seem…bitter about dating. This is a sign that they’re probably not going to be a great partner: even if they’re not hung up on their ex(es), they’re clearly harboring some negative romantic energy, and you don’t have time for that.^{[8]
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4
They’ve got trust issues. If your date isn’t over the hurt that a past marriage caused, it’s possible they’ll go into a relationship with you with their hackles up. This might be a sign they’re struggling with opening themselves up again, and that they’ve still got a ways to go to heal from their last relationship.^{[9]
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- You can take it slow with someone like this, if you feel like it’s worth it. But don’t expect any change here—remember, attach to the person you’re dating, not the person’s potential.
5
They haven’t been single very long. If someone starts trying to date immediately following the dissolution of their last relationship, it could be a sign that they don’t know who they are outside of their romantic relationship—and they might be looking to you to fill the void left by their last partner. This isn’t to say “never date someone newly single!” but…go very, very slow. The last thing you want to be is a rebound.

Section 4 of 5:

Red Flags When Dating Widows/Widowers

1
They’re still mourning their spouse. Losing a spouse is almost unbearable. If you’re dating a widow or widower, they might still be experiencing tremendous grief over the loss of their former love—and they might always feel some grief. But if their grief inhibits their ability to fully give themselves to a new relationship, it might be best to step back: your date might just need some more time to mourn and come to terms with their loss.^{[10]
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2
They feel guilty for dating someone new. Even if your date has begun to move on from their former spouse, they might struggle with feelings of guilt over dating someone else. This is very common, and it doesn’t have to interfere with your relationship—but it certainly can. You deserve someone who will love you fully and without any guilt.^{[11]
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- It can be tough for someone who lost a partner to introduce a new romantic interest to their friends and family, especially children, if they had any with their previous spouse.
- You can be patient and understanding here, but if a few months go by and your date shows no sign of involving you in their life, it could be a sign they’re not ready to.
3
They’re living in the past. Your date might be really into you, but if they’re hung up on their former life, they might not make the best partner. Note if your date always brings up their past with their late spouse, or if they constantly compare your relationship to their previous one. A little nostalgia is healthy and normal, but if your date is living in the past, it might be best to leave them there.^{[12]
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Section 5 of 5:

Signs of Narcissism

1
They think they’re better than you. OK, tips for identifying narcissists isn’t unique to daters over 50, but it never hurts to remind ourselves of the red flags! A narc will suffer from a superiority complex—and it probably won’t be that hard to identify. If your date just has to be the expert on everything, and if you feel pressured to defer to their judgment and preferences over your own, you’re probably dating a narcissist.^{[13]
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Trustworthy Source
PubMed Central
Journal archive from the U.S. National Institutes of Health
Go to source}
2
They’re self-centered. Not only are they king or queen of the castle, they’re the only one IN the castle. For a narcissist, the only one who matters is themselves: everyone else might as well not even exist.
3
They keep secrets. You might have to date them a little while to identify this red flag, but if they’re a narcissist, it’s there. Narcs are obsessed with their self-image, and they are also notorious for not always treating the people in their lives the way they should. If your narcissist is concerned about looking a certain way to you, or if they’ve done something wrong and don’t want you to find out, they’ll probably tell you a few lies. Once you catch them, it’s best to just cut and run.
4
They make you question your sanity. Narcissists are masters of gaslighting, or making you think that what you perceive to be reality isn’t actually reality at all. Pay attention to how you feel around this person: if they’ve constantly got you doubting yourself, they may be playing mind games with you.