13 Common Red Flags When Dating in Your 50s


You’re back in the dating game after decades of marriage, and the rules have changed. 

As you wade into these uncharted waters in your 50s, you need to keep your eyes peeled for red flags that could indicate bigger issues down the road. 

With life experience under your belt, you know that every budding relationship requires compromise, but there are dealbreakers that should give you serious pause. 

Read on to learn the 13 most common red flags that can pop up when dating after 50 so you can spot trouble early and protect your peace of mind and happiness.

13 Most Common Red Flags When Dating in Your 50s

As you get back out there after 50, it’s important to recognize potential red flags that could indicate challenges down the road.

couple sitting at bar Red Flags When Dating in Your 50s

Pay attention to these common issues that tend to pop up more often at this stage of dating so you can proceed thoughtfully and with realistic expectations.

1. They’re Not Financially Stable

If you date someone who’s dealing with money problems, this can quickly spill over into your life, too, if things get serious. You don’t want to deal with constant hounding from creditors or requests to borrow money. 

Be cautious if they seem to spend excessively or make very little money without any savings or retirement plan. This might mean you’d have to bankroll their lifestyle if things progress.

2. They Have Very Different Relationship Goals 

Perhaps you’re hoping for companionship while they’re seeking something long-term. It’s key that you’re both open and honest about what you want. If your relationship goals aren’t aligned, one of you may end up disappointed. 

Clearly communicate your vision for the relationship so you don’t waste each other’s time if they don’t sync up.

3. You Don’t Share Core Values

Differences in small things like favorite foods or hobbies are one thing. However, gaps in significant areas like politics, religion, family, and financial values can be relationship dealbreakers. 

If your core beliefs and priorities aren’t compatible, it will cause tension and conflicts. You and any potential partner should see eye-to-eye on the things that really matter to each of you.  

4. There’s Drama With Their Ex

No one wants to deal with a vindictive ex still interfering in their partner’s life. If they’re constantly battling over money, kids, or other unfinished business, you’ll get caught up in the drama, too. 

This might mean last-minute cancelations on dates or taking a backseat while they deal with emergencies. Make sure any past relationships are fully in the past.

5. They Have Unrealistic Relationship Expectations 

Some people enter the dating world after 50 with a checklist of must-haves for a partner that are highly unlikely or even unreasonable. 

We all have preferences, but having rigid expectations rather than wishes almost always leads to disappointment. Check any demands or unrealistic criteria at the door and keep an open mind.  

6. Their Friends and Family Don’t Approve of You

Hopefully, the people who care about your potential partner have good intentions for them. If you notice ongoing tension or outright disapproval from their loved ones, pay attention. 

There may be legitimate concerns or incompatible lifestyles at play. If their inner circle just can’t warm up to you, it will strain the relationship.

7. They Seem Self-Involved and Self-Absorbed

A healthy relationship requires give and take from both people. If your partner dominates every conversation, always steers it back to themselves, and seems uninterested in you, this is a bright red flag. 

You want someone who actively listens, asks questions, and shows that they care about you, too. Self-absorption does not make for lasting romance. 

couple standing outdoors  Red Flags When Dating in Your 50s

8. They Have Anger Issues

We all get annoyed or upset at times, but intense, frequent anger that seems out of proportion to the situation can signal deeper problems. 

Uncontrolled rage, angry outbursts, intense mood swings, and short fuses are not something you should have to tiptoe around. This volatile behavior can escalate over time, so don’t ignore it. Everyone deserves to feel safe and respected.

9. They’re Controlling and Possessive 

You likely have your own preferences and ways of doing things, but a controlling partner will insist you change to suit their needs. This might begin subtly with small demands that increase over time. 

A healthy relationship allows both individuals autonomy over their own lives. Jealousy and possessiveness are also signs this could become unhealthy. You want an equal partnership, not a parent.

10. They Have a History of Serial Dating and Multiple Divorces

There’s nothing inherently wrong with having been married more than once. However, if a potential partner has a long and winding trail of relationships and marriages throughout their life, this may signal a pattern of instability. 

Be wary of someone who can’t maintain commitment for long or seems to bounce quickly from one ex to the next.

11. They Don’t Make Time for You

In the early days of dating, you want to see frequent interest and effort made to spend time together. Take note if someone continuously cancels dates or isn’t as available as you’d hoped. 

You don’t want to feel like an afterthought to them. Make sure the person is as excited about getting to know you as you are about them.  

12. They Want to Get Too Serious, Too Fast

While some are in it for the long haul, it’s fine to just test the waters at first. But a potential suitor who gets heavily emotionally invested immediately or rushes important commitments sends up a caution signal. 

Moving very quickly often backfires once the initial spark fizzles. Take your time and let true feelings develop at a healthy pace.

13. Your Gut Says Something is Off 

Even if you can’t quite identify the reason, that nagging inner voice should never be ignored. Our intuition picks up on more subtle concerns due to life experience. 

Related: 27 Gut-Feeling Signs You’re Meant to Be with Someone

If someone makes you feel unsettled or uneasy for some reason you can’t pinpoint, believe that instinct. At a minimum, move cautiously until you figure out the vibe.

What Should You Do If You See These Dating at 50 Red Flags?

Getting back out there after 50 can be emotionally charged, especially if you spot some concerning behaviors early on. While no new relationship is 100% smooth sailing, certain red flags deserve your thoughtful attention. 

Don’t ignore signs that core compatibility could be lacking. If you notice any of the warning signs we covered, here are some tips:

  • Check your own baggage first – Examine your relationship patterns to ensure you aren’t projecting or overreacting.
  • Communicate clearly – Voice concerns calmly, set boundaries if needed, and give feedback on specific issues.
  • See if compromise helps – For smaller differences, meet halfway when possible if you think the relationship has potential.
  • Pay attention if multiple flags appear – A problematic theme likely means time to reevaluate or move on.
  • Trust your instincts – If something feels off and doesn’t get better over time, believe your inner guidance.
  • Seek outside perspective – Get insight from a trusted friend or mental health professional.

Stay centered in yourself, voice needs assertively, and don’t compromise personal dealbreakers. You deserve fulfilling love with someone who cherishes you.

What About the 50 and Never Married Red Flag?

So there’s this great person you met who seems loving, mature, and ready for commitment. But wait—they are over 50 and have never said, “I do?” There’s no need to view a solo relationship history as an automatic red flag. 

Perhaps they prioritized purposeful career building, focused on self-growth after college, or cared for aging parents during prime marrying years. Some people wait to meet a deeply compatible partner rather than settle. 

Get to know their dating outlook, values, and relationship skills. Assess emotional availability, not numerical tallies. An open heart bears no age. What matters is the present you are building together, not the past.

What Are the Rules for Dating After 50?

Jumping back into the dating scene after 50 can feel like an overwhelming, uncertain new frontier. Maybe you were married for years before finding yourself single again, or perhaps you’ve been in and out of several relationships over your lifetime. Either way, knowing the current “rules” for dating at this stage will help you navigate things more smoothly. Here’s what you need to keep in mind:

Forget any preconceived expectations – Dating looks different now than 20 or 30 years ago, so let go of any notions from past experiences. Be open-minded about how people now connect, communicate, and form bonds.

Take your time getting to know potential partners – There’s no need to rush into anything serious right away. Date casually at first to see if you genuinely connect, share chemistry, and align on major values.

Clearly communicate what you want – Are you ultimately hoping for a life partner or just looking for companionship and fun? Being upfront about relationship goals from the start prevents misunderstandings.

Address dealbreakers early on – Certain key areas like financial stability, future plans, or coping with exes need to be discussed sooner rather than later. Don’t ignore possible red flags.

Prioritize compatibility above all – Shared interests, mutual respect, comfortable communication, and freedom to be yourself are the ingredients for relationship success at any age. Focus on finding those essential elements above all else.

What Are Relationships Like in Your 50s?

You’ve got decades of romantic experience under your belt. By this stage, you’ve learned that relationships are too complex to generalize or reduce to easy formulas. With age comes wisdom—and, for many, a peace of mind about partnerships. Emotional intelligence is earned over time. 

At last, you understand the balance of compromising versus setting healthy boundaries, embracing vulnerability after loss, and communicating needs comfortably. You accept what all long couplings share—both joyful and challenging moments. 

Drama and games hold little appeal. Instead, you seek true connection, a love who shares the real you, laughter that weathers long years. That sort of relationship may just await you.

What Do Men in Their 50s Want in a Woman?

As men settle into their 50s, many start thinking differently about what they really want in a romantic partner. While physical attraction still matters to most guys even at this stage, other wishes take higher priority after they have more experience in relationships under their belts. Here’s a peek at what men over 50 often hope to find in a woman:

Emotional Maturity

By this decade, men have typically gained a lot of self-awareness. They look for a grounded woman who has also done the personal work to understand emotions and communicate in a healthy way.


Rather than getting caught up on surface details, men moving through midlife want a woman with shared values and outlooks on key areas like family, finances, spirituality, leisure, and community. Alignment in the areas that really count is crucial.


After potentially having been through a divorce or former relationships with very needy partners, men want a woman who is stable and self-assured with her own fulfilling interests and friends outside the relationship. 


Many midlife men hope to travel, enjoy hobbies, and simply savor life with someone special by their side to provide close companionship through the ups and downs.

What Is the Biggest Red Flag in a Guy Over 50?

By the time men pass the half-century mark, they have likely done a fair share of self-work when it comes to managing emotions, communicating needs, and showing up fully in relationships. 

As such, one of the biggest red flags to watch for in a potential partner over 50 is clear evidence that none of that personal growth has taken place. 

Lack of self-awareness, emotional unavailability, avoidance of commitment, and inability to identify why previous relationships didn’t pan out are all warning signs that this could be a rocky road ahead. Proceed carefully if you spot these signals.

Final Thoughts

As you navigate the modern dating landscape after 50, remember that wisdom and self-knowledge are on your side. Approach new relationships with openness, honest communication, and trust in your ability to spot compatibility versus red flags. Don’t ignore warning signs, but also let each budding romance unfold organically. Here’s to new adventures and lasting love!

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