Dating At 50? The Red Flags You Need To Know!

Dating at any age can be a blend of excitement and anxiety, but for women over 50, it carries its own set of challenges.

It’s often humorously said, “Dating after 50 is like finding the least damaged item at the thrift store that doesn’t smell!”

Whether or not you find that quote funny, it rings true that as we mature, we come to recognize the importance of identifying potential red flags in our romantic pursuits.

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10 Red Flags for Dating After 50

With 26 percent of adults aged 50 and older diving into the dating pool via apps and online services, awareness is key to navigating these waters safely and successfully.

Truth be told, it’s a little scary to be dating after 50. As you meet new people, try and focus on the lessons that life has taught you. Most people sincerely try to be the best person they know how to be. But some people have the potential to be hurtful and possibly even destructive.

This list is not a complete dictionary of dating red flags, but if you pay attention to these behaviors, you should be able to avoid hooking up with mediocre, middle-aged, greasy men.

1. Inconsistent Communication

Consistent communication is a cornerstone of any emerging relationship. If your date is regularly canceling plans, not returning messages, or vanishing for days without a word, it could indicate a lack of serious interest or commitment.

Healthy communication is based on respect for the other person and the relationship. When a romantic partner struggles or fails to communicate regularly, it may be a sign of disrespect.

We all have our communication styles, and many of us don’t take the time to explore if we are good communicators. Your potential partner may be unaware of his inability to communicate clearly. We all can get caught in “lazy” behavior until we are challenged to level up in our romance game.

Poor communication is a dating red flag.

The best way to find out if your partner is willing to make communication changes is to have a frank conversation. It might feel uncomfortable if you are still in the early dating stages, but starting with a solid commitment to truth-telling and vulnerability is better.

If we ignore red flags in relationships, we are saying that whatever the other person does is acceptable to us. It will be nearly impossible to try and “fix” the painful problems if we have self-abandoned and allowed them to continue.

2. Lack of Transparency

Honesty is crucial in building trust. If someone is vague about their past, dodges questions, or has stories that don’t add up, they may not be as open as you would need them for a healthy relationship.

Is there anything worse than feeling like you can’t trust someone?

When dating someone new, you count on them to be truthful and transparent. We all have histories, but when dating someone new, you rely on the other person to share their past lives accurately.

Trust your gut. Ask the “icky” questions and expect grown-up, adult answers. If you aren’t getting the sense of safety you need, it’s probably time to move on.

3. Unwillingness to Commit

Watch out for individuals who shy away from labeling the relationship or discussing the future. They might not be ready to settle down if they’re always steering clear of commitment talk.

Let’s also state the obvious: it’s okay if you DON’T want a commitment. It is perfectly fine for you to want to keep things light and open; plenty of women don’t want a ring and vows.

But, if you want a level of commitment in your relationship, be clear. If you need a monogamous commitment, state it with clarity. Maybe you want to try dating around before committing to something exclusive; explain your desire with confidence.

The issue of lack of commitment grows like a fungus in the dark! There is not enough light; it’s a little dank, and questions start popping up everywhere! Be kind and be clear on your expectations with your potential new romantic partner.

4. Financial Instability

While money isn’t everything, a partner with significant debt, no savings, or a habit of asking you for loans might not be in the right position to be part of a stable partnership.

This is generally a major red flag. If an adult cannot manage their money, then be very wary of starting a relationship.

Yes, we all have been kicked in the dollars, but by midlife, most folks should be able to identify and take ownership of their dysfunctional financial patterns. They should be working to remedy their problems and moving toward economic stability.

5. Disrespectful Behavior

Pay attention to how your date treats you and others around you. Rudeness to waitstaff and other drivers on the road, an irritable attitude, or derogatory remarks are signs that they may lack the basic respect essential in a partner.

Respect is usually learned during our childhood formation. It cannot be easy to be in a relationship with someone who missed out on early lessons of respect for everyone. This includes gender, body size/shape, sexual preferences- you get the idea….

We don’t have to agree or affirm other people’s choices, but we want a partner who can display basic respect for other human beings.

Disrespect is never attractive; don’t put up with that type of behavior.

6. Excessive Baggage

Everyone has a past, but if your date is perpetually caught up in drama from previous relationships or unresolved issues, they may not be ready to start something new.

Sadly, some people live in chaos. They learned that drama and despair make them feel needed or “normal.” These folks typically come from homes with challenging circumstances, and they learn to accept and adapt to the dysfunction to survive.

If you are dating someone who has perpetual drama issues, gently suggest that they need help from a mental health professional. If they resist, it is time to take a break and wait to see if they can get control of their maladaptive patterns.

7. Controlling or Manipulative Behavior

Your date should never try to dictate your wardrobe, influence your choices, or isolate you from friends and family. Control and manipulation are serious red flags that often herald an abusive relationship.

Controlling behavior also includes the use of passive-aggressive language.

Passive aggression is a way of expressing negative feelings, such as anger or annoyance, indirectly instead of directly. Passive-aggressive behaviors are often difficult to identify and can sabotage relationships at home and at work.

Despite your best efforts, it is never your job to help other people improve their behavior. If you find your dating life riddled with passive-aggressive people, it might be time to find out why you are attracting this type of unhealthy partner.

8. Lack of Emotional Availability

They might be emotionally unavailable if your date seems detached, disinterested in your feelings, or unwilling to share their own. A fulfilling relationship involves emotional depth and vulnerability on both sides.

You already know this, but we all start as babies. Babies rely on the big people to take care of us; we can’t survive without their help and nurture.

For some of us, we learned that the best way to get what we need is to hide our emotions. Many families have discouraged the expression of negative emotions for generations.

As a result, millions of adults have been trained to ignore their feelings. If you are dating someone who is emotionally “constipated,” it is very likely they don’t know how to have feelings. This can affect your communication and your intimacy.

Again, this type of problem is best helped by a supportive mental health professional. It isn’t easy to be the girlfriend of a man who can’t open up to you. You will frequently feel isolated and alone and most likely will not be able to have meaningful conversations or productive conflict.

This type of relationship will fail to grow because one of the partners struggles with a fear of vulnerability.

Emotional connection is key to a healthy romance.

9. Incompatible Values and Goals

While opposites can attract, significant differences in lifestyle choices, ambitions, and moral values might be impossible to reconcile in the long term. Ensure your most essential values align.

By the time we reach middle age, we should have a solid set of ethical and moral principles that frame our lives. Don’t compromise them when looking for a romantic partner. Hoping your good character “rubs off” on your new boyfriend is not a smart strategy.

Don’t compromise. You will regret it.

10. Lack of Effort or Investment

A relationship should be a two-way street. If you’re always the one making plans, initiating communication, and pushing things forward, it might be time to ask yourself if you’re being valued as you should be.

Make sure that you clearly state your expectations from the other person. Sometimes, we find ourselves with a romantic partner who can only meet our needs halfway, which is okay. It doesn’t always mean a person is dysfunctional or “broken.”

It’s never too early in a relationship to start observing patterns and behaviors, both positive and negative. Start to share your well-defined “reasonable” expectations with the first month of dating. If you find that you are incompatible, moving on is perfectly okay.

Final Tips for Dating at 50

Remember, the key to any healthy relationship is to build on a foundation of trust and vulnerability. The only way to build a true “romance” is to show up as your most authentic self. Don’t compromise by lowering your standards or ignoring possible red flags.

TL;DR If your gut tells you something is wrong, pause and investigate.

It’s Not Easy, But It Will Be Worth It

In the later years of dating, it’s vital to be aware of the warning signs that may indicate potential problems in a relationship. Ignoring character flaws or misusing bad behavior in your relationship devalues your worth.

By identifying the red flags of dating at 50, you stand a better chance of finding someone who complements and cherishes you. Always prioritize your self-care and well-being, and remember that the right person will celebrate your worth and add to your happiness, not detract from it.

What other “red flags” would you add to this list? Drop your comment below!

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Melane Ann is a writer, blogger, and life coach. In 2020, she turned her experience in midlife divorce and creating a new life for herself into midlifeismagical. With a master's in Marriage and Family Therapy, Melane focuses on helping women over 50 navigate their relationships and commit to healthy aging. She and her new husband share 7 children between them. Melane jokes that she has a black belt in blended families! In addition to her writing, Melane works virtually with her coaching clients from her home office.

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