Dating can be scary, confusing, and frustrating. This is especially true if we’re returning to dating in our fifties or later, after divorce or loss of a spouse.
We all want to feel safe, respected, and loved. Sadly, a few unpleasant dates with the wrong kind of partner can stop us from putting ourselves out there.
The other thing about dating in our 50’s or 60’s is that there are a few lifestyle factors to consider that we didn’t have to think about in our younger years. For example, children, extended family, health, and financial status are important areas that have their own red flags.
One tool to use in your search for better partners is to recognize red flags when dating an older man or woman.
It took me many years to learn (through therapy) that the early warning signs to my failed relationships were plain to see, right from the beginning.
A dating red flag doesn’t necessarily rule someone out. It does, however, signal that it’s a good idea to look more closely at yourself and your potential partner.
10 Types of Red Flags When Dating
With that in mind, here are major dating red flags to look out for to avoid a troublesome relationship after the dating ends.
I sorted them into ten groups:
1 – Internal Red Flags in Dating – Your Behavior
2 – Common Red Flags in Dating – Partner Behavior
3 – Red Flags That You’re Dating a Narcissist
5 – Red Flags for Love Bombing
6 – Red Flags About Past Relationships
7 – Red Flags Related to Communication
8 – Red Flags Related to Personal Hygiene
9 – Red Flags About Personal Boundaries
10 – Red Flags Related to Compatibility
Internal Red Flags in Dating – Your Behavior
I come from an alcoholic family in which “be seen, not heard” was the rule. To draw attention to myself was to invite trouble, especially after my dad’s drinking had started.
The result was that I learned how to ignore my intuition and bury my feelings.
Intuition is our sub-conscious mind at work awake or asleep. We know it as hunches or gut feelings.
One of the most helpful things I ever learned about relationships was that I should always listen to my intuition.
Until I was in my fifties, I ignored or discounted my intuition in every personal or professional relationship.
I remember at the beginning of one long-term relationship my inner voice repeatedly said, “Do NOT get involved!” Over and over. I recall saying it out loud to myself. I ignored it. She thought it was a good idea for us to date, so I went with her opinion. A few years later it ended.
A wonderful therapist helped me to connect the dots on why I did this over and over in my life. The result was that I started to listen to my gut.
If you get nothing else from this article, take this dating red flag to heart:
🚩 Your gut is telling you, “Don’t do this!” or “Something’s not right.”
Listen to your inner voice. It may not have all the answers, but it’s working in your best interests. Take time to review the issues that are coming up. Talk about it with trusted friends or a therapist, just to ensure you’re on the right track.
Aside from intuition, there is another “internal red flag” when it comes to dating.
🚩 You find yourself engaging in obsessive or destructive behavior.
Perhaps you started drinking more. Or eating, or gambling. Negative behaviors could be a sign that you’re avoiding an important issue. They’re also a sign that you may not be quite ready for a relationship.
Common Red Flags in Dating – Partner Behavior
If you see these behaviors from your dating partner, it signals something is not right with them or with their ideas of a healthy relationship.
🚩 Hypochondria (Illness Anxiety Disorder)
They display abnormal anxiety about their health, even when they have no evident physical symptoms.
According to Mount Sinai hospital, hypochondria can be the result of the person having learned the attention-getting benefits of being sick. Or they may have other anxiety or obsessive compulsive disorders. The bottom line is they’ll have a tough time entering a genuine two-way relationship.
🚩 Drinking excessively.
Plenty has been written about the damaging effects of alcohol on relationships and the human body. It’s also a symptom of deeper relationship issues rooted in childhood.
🚩 Getting very personal on the first date.
The first date is a general get-to-know-you experience to see if there is any compatibility. Deeper knowledge should come later in the dating journey.
🚩 Talking about sex right away.
This is probably a sign that sex, not a relationship, is their primary interest. However, if that’s what you both want, then you’re on common ground.
🚩 Rudeness and disrespect for others.
If they’re disrespectful to a waiter, it won’t be long until they’re rude to you or your family.
🚩 Talking about an ex on the first date or two.
The details about each of your personal lives will come later. The first dates are a search for compatibility. If there is anger involved in talking about the ex, steer clear. There are unresolved issues.
🚩 Not listening. Monopolizing the conversation.
Ugh. This type of person will always, and I mean always, monopolize any and all conversations. I overlooked this red flag and can say from years of personal experience, it is tiresome. It does not change.
🚩 They lie.
I had one date who lied outright about her dating profile. I was making small talk and asked her about one of her interests in exercise. I had memorized this and a few small-talk points directly from her profile. She said she never did anything of the sort and looked at me like I was nuts.
I checked when I got home, and sure enough, it was there, plain as day. No second date.
🚩 Their grown children or other family are living with them.
This is only a negative if you’re not OK with the situation. Just be sure to acknowledge your own feelings and wishes before going further in your dating journey.
🚩 Excessive debt or financial insecurity.
A partner’s financial situation is important. Opportunities for changing this are not the same as when we first started out. It needs to be in sync with your vision.
🚩 They insist on meeting at your house or an isolated place.
Don’t. Always use safe, public places for your first dates. We always recommend a coffee date as the best first date.
🚩 They insist on picking you up.
Always use your own transportation and meet at a safe, public place. Have your cell phone charged and let a friend or family member know the details of your dating plan.
Red Flags That You’re Dating a Narcissist
In 9 Signs That You May Be Dating a Narcissist, Daisy lists some of the red flags that you’re dating a narcissist.
I list these in their own group because of the nature of narcissism. The problem with narcissist is not that they can’t change.
Dr. Craig Malkin, writing in Can Narcissists Change? says,
“It’s not that people with NPD can’t change; it’s that it often threatens their sense of personhood to try. And their failed relationships often confirm, in their minds, that narcissism is the safest way to live.”
The odds are that they won’t ever change. Remember, you’re dating. It’s not your job to change another to suit your needs. Narcissistic behavior is impossible to live with in a healthy way. Move on.
Here are several signs you might be dating a narcissist.
🚩 Grandiose self-importance
They exaggerate their achievements and talents.
🚩 They believe they are special and should only associate with other “high status” people or institutions.
🚩 Needs excessive admiration.
🚩 Has a sense of entitlement.
🚩 Is inter-personally exploitative.
They take advantage of others to achieve his or her own ends.
🚩 Lacks empathy.
They are unwilling to recognize or identify with the feelings and needs of others.
🚩 Is often envious of others or believes that others are envious of him or her.
🚩 Is arrogant and haughty.
🚩 Wears flashy clothing.
🚩 Brags about their “perfect” family.
No one has a perfect family or a perfect life.
🚩 Excessively generous.
At first this may seem like a positive trait. They give freely and to excess in public, but it’s to demonstrate their power. In private they are cold or indifferent.
🚩 Hypersensitive and insecure.
They get wildly defensive at the smallest criticism.
🚩 Puts down other people yet will mention others to name-drop.
🚩 Loves to talk about themselves.
Self-interest rules their life. They love to talk about themselves and be the center of conversations.
Dating Scam Red Flags
Here are some warning signs you might be in contact with a scammer.
🚩 They send disjointed emails
In this article on first dates, Daisy writes about how she recognized online dating scammers via their emails:
“Some wrote me disjointed emails that didn’t make a lot of sense. They included lots of references to how beautiful I was and overall read like someone for whom English was not the first language. They said things that didn’t really relate to me. I figured they were form letters intended to win me over and then they’d ask me for money.”
🚩 They never want to meet in person
This is a sign that they are married and dating on the sly, or they’re financial scammers.
🚩 They write lots of long letters to build trust.
Then they’ll ask for money because of a fake emergency.
🚩 They use poor grammar.
Their messaging is intentionally faulty. Some examples that Daisy mentions include, “My heart good for you” or “Nice you. Pretty lady.” Those who respond are considered easy targets.
🚩 They want to move communication off the dating site.
The messaging in dating apps and sites is very secure. Don’t move to email, phone or in-person until you are ready.
🚩 Their online dating profile is fishy.
If you don’t trust their profile, use the reverse image search on Google images. If the images show up as associated with someone else, or as a stock image, their profile is probably bogus. Check their social media profiles, too. These give clues as to their authenticity.
Red Flags for “Love-Bombing”
Love-bombing is a manipulative dating practice in which the partner wants to sweep you off your feet and make it seem like you are “the one.”
The problem is that their attention flows in one direction. It’s a subconscious way to control the other person.
They are often narcissists or have other personality disorders. There is no chance for a healthy two-way relationship.
Some of the red flags for love–bombing:
🚩 Excessive gifts right from the start.
Although it feels good at first, I recall being uneasy about some large gifts at the beginning of one relationship. Again, I ignored this and several other early warning signals!
🚩 Excessive texts, emails or phone calls.
One night after dinner with my ex-girlfriend at her home, I left for my place just minutes away. She insisted I call when I got home even though I was wide awake and a non-drinker. One minute out from her driveway I got a call. Then another call as I pulled into my drive. You get the picture. It’s too much and it was indeed a sign of deeper problems.
🚩 They claim immediately they found their soulmate.
Or perhaps you’re “instant best friends.” Remember, it always takes time to get to know someone well.
🚩 Incongruent behavior.
Their behavior doesn’t match their words. For example, you’re “the one” yet they disappear without explanation.
🚩 They hint at a punishment or repercussion when you can’t accommodate a request.
For example, perhaps you don’t want to go on a trip with them, yet they react poorly.
🚩 It seems too good to be true.
That feeling is a signal to give it time. If the love bomber won’t move slowly, that’s your signal to move on.
Red Flags About Past Relationships
If you find yourself dating in your 50’s after divorce, it’s almost certain there will be past relationships in your partner’s life. How does your potential partner talks about their past relationships?
🚩 Do they blame their exes for everything?
🚩 Are they still hung up on an ex?
🚩 Do they talk about their exes in a derogatory way?
Red Flags Related to Communication
How does your potential partner communicate with you?
🚩 Do they take a long time to respond to messages?
🚩 Do they cancel plans at the last minute?
🚩 Do they avoid having serious conversations?
Red Flags Related to Personal Hygiene
🚩 Does their personal hygiene give you pause for thought?
While this might seem like a small thing, it’s important to pay attention to personal hygiene when dating. If your potential partner has poor hygiene or doesn’t take care of themselves, it could be a sign of larger issues.
Red Flags About Personal Boundaries
Does your potential partner understand and respect your boundaries?
🚩 Do they pressure you into doing things you’re not comfortable with?
🚩 Do they try to control your behavior or decisions?
Red Flags Related to Compatibility
Are you and your potential partner on the same page when it comes to important issues like religion, politics, or family values?
🚩 Are they dismissive of your beliefs?
🚩 Do the two of you have similar goals for the future?
If you’re not compatible in areas that are important to you, it will likely lead to problems down the road.
Final Thoughts on Dating Red Flags
So, this lengthy list is not intended to scare you away from dating. Instead, it’s meant to make it easy to spot potentially troublesome relationships before they ever get too far.
It’s not your job to fix the issues with your dating partners. An awareness of the red flags when dating an older man or woman makes it easier to have more fun.
I also suspect that having read this list, your subconscious will file them away for future use. If you find that little voice nagging you about your latest date, listen to it.
If you have any red flags to add, use the comment section below. Or share your dating stories here and get a Free copy of Is Online Dating Better Than Traditional Dating?
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