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Dating for Older Singles - What to Watch out for

Updated on January 20, 2017

Dating can be daunting especially if you’re jumping back in the saddle again after a breakup, divorce or death. I have heard almost every older person say, “If something happens, I’ll never get married again” or “I’m done with the opposite sex for good.” But time passes and has a way of healing and then older singles can find themselves alone while all their friends have partners. And being alone can get old fast. It is human nature to want to share our lives with someone.

That said, I still laugh at a joke that goes something like this: “At my age, finding someone is like finding a parking space – all the good ones are taken and the rest are handicapped (emotionally that is).” Yes, it can be slim pickings and those of us who have lived awhile can come with our own drama-filled past. Therefore, older singles are on good behavior and it can be tough to spot the warning signs that tell us the person we are hanging out with is less than ideal for us.

Here are four dating red flags that might help you decide if you should continue to go out with someone or not.

red herring


something intended to divert attention from the real problem or matter at hand; a misleading clue.

Red Herring #1 - Pushy Pants

Pushy or manipulative people can be tricky to spot especially if subtlety comes into play which is how someone who just met you is likely to display this tactic. “The manipulators,” according to author and management guru M.S. Rao, “often talk about individuals and issues but not ideas. They exploit the weaknesses of others and leverage their strengths.”

How this might appear – Couple #1 (Carol and Matt)

Background: Carol and Matt have had one first date. They really hit it off. Carol did notice Matt seemed a bit pushy, but she chocked it up to his confidence. When Matt called Carol for a second date, it went something like this:

Carol: No, Matt, thank you for asking, but I can’t go to the movies with you tonight, I promised my son I would babysit.

Matt: Babysit?' (Laughing) Really? You’d rather babysit than go to the movies with me? Everyone is dying to see this movie. You could babysit your grandchild anytime.

Carol explains to Matt that she has promised her son and his wife a well-needed night out, but Matt persists and focuses on Carol making her increasing uncomfortable and causing her to feel bad about herself.

Matt: Well, I’m a pretty popular guy and I’m sure I can find someone else to go with me if you won’t agree.

Carol: You do that.


Go Carol! Notice she does not tolerate Matt’s emotional blackmail. If a date asks you to do something, you have a right to say “yes” or “no” without offering tons of explanation and arguing about why or why not. A respectful individual might instead say something like this: “I’m sorry you can’t make it. I’ll call you again sometime. Enjoy watching your grandchild. Family is important.”


Red Herring #2 - Makin' me Crazy

Sometimes crazy is easy to spot and sometimes it’s not. But the easiest way to spot crazy is to monitor how you feel around that person. Do they make you feel like the “crazy one"? The double bind is a theory that according to Dr. Jeremy Sherman, is a “… three-way, no-win situation that amounts to you're damned if you do; you're damned if you don't, and you're damned also if you notice that you're damned either way. In other words, by jerking you around, I'll make you feel powerless and if you try to escape my jerking, I'll make you feel even more powerless."

If something doesn’t feel right to you, it probably isn’t. Learning to trust your instincts is an essential key when dating.

How this might appear – Couple # 2 (Melanie and Doug)

Background: Melanie and Doug have been dating 6 months. It’s been rocky, but they have a very passionate, crazy love. Doug had a fishing trip planned long before he met Melanie and she is struggling with him spending a weekend with his cousins at fishing camp.

Melanie: You’re leaving for camp. Don’t you love me?

Doug: Of course, I love you.

Melanie: Then why would you leave?

Doug cancels his fishing trip and spends the weekend with Melanie. His cousins joke that he is “whipped”.


No-win questions are what often put people in a bind. According to Kevin Evertt FitzMaurice, “If you say 'yes,' then the response is to ask why you didn't or don't then do what you should if you know what to do. If you say 'no,' then the response is you are defective, bad, worthless, stupid, etc., for not knowing what you should do: the right thing according to their values.”

In the long run, Doug is the one who ends up feeling crazy here as Melanie puts him in a no-win situation where he feels damned no matter which way he turns. A relationship with Melanie, if they continue along this path, will leave him drained and controlled and eventually looking for a way out of her trap.

How long should it be before you tell someone you love them?

See results

Red Herring #3 - Speedy Lover

Love too soon can be a dangerously hard morsel to push away. After All, when you have chemistry with someone, you just know it, right?

Educator Andrew Galperin says it may be more complex than that, " may have evolved to fall in love first, in order to show their commitment to women." Typically, Galperin says, "men fall in love more easily than do women."

In another of Galperin's hypothesis, he says, "Individuals who over perceive others' sexual interest will report falling in love more frequently." The danger here is that perceptions are not always correct.

I remember a friend telling me about a man who interpreted her statement that her children where spending the night with their father as an invitation for sex. He pumped himself up with Viagra and, although it was only their 2nd or 3rd date, started pushing for sex. When she resisted, he questioned her - "Wasn't this what you were hinting at when you said your kids were with their dad?"

And finally, according to Beth Livermore in a Psychology Today article, "We now know that it is the insecure rather than the confident who fall in love most readily." Watching to make sure you aren't the next "hero" to someone with a past of insecurity issues, is very important.

How this might appear – Couple # 3 (Cheryl and Donald)

Background: Cheryl and Donald had been on two dates. Cheryl wasn't feeling much chemistry with Donald, but she was bored and he did seem like a nice guy. Donald, on the other hand, had a much different view of their relationship. He had been deeply hurt by his X-wife and had been struggling with insecurities when it came to woman. He was smitten with Cheryl.

Donald: I could so easily fall in love with you.

Cheryl: (uncomfortable) Really?

Donald: Yes, in fact you are the woman of my dreams. I love you like I never loved anyone else!

Cheryl: But I thought you were married to your wife for over 25 years. We've only know each other 2 weeks.

Donald: But this is different, I can tell.

Cheryl then has the unpleasant job of telling Donald that, although she really likes him, she is not in love with him and, not wanting to lead him on, she rejects all offers for another date.


Just because some men may fall in love more easily does not mean that women need to then agree with their declarations. When dating someone with insecurities, watch out for premature affirmations of love. And finally, some people just might have the sex and love thing all mixed up.

10 Ways to Spot a Liar (summary of an article on WebMD by Heather Hatfield - reference below)

1. Look for inconsistencies. Is there something that doesn't fit the story?

2. Ask the unexpected. Catch them off guard and see how they respond.

3. Gauge against a baseline. Is behavior different from their normal behavior?

4. Look for insincere emotions. Is that a fake smile? The emotions don't fit the situation.

5. Pay attention to the gut. What we are really picking up is subtle deviations in true emotions.

6. Watch for micro-expressions. This is hidden emotion that appears in the blink of an eye. Is someone happy, but their face just briefly flashed anger. Tough to spot, but can be learned.

7. Look for contradictions. Do gestures match words such as saying "no", but shaking the head "yes".

8. A sense of unease. Is the person making eye contact, sweating or anxious?

9. Too much detail. This crafted story can be a solution to a lie.

10. Don't ignore the truth - it can sometimes be buried in a lie which can eventually get at the heart of the problem - why someone is lying in the first place.

Red Herring #4 - Sneaky Snake

"Now," says Heather Hatfield, in a WebMD article, "the average person can become adept at identifying dishonesty, and it's not as hard as you might think."

Sneakiness is just plain old dishonesty - trying to cover up your actions or whereabouts and if you're in the dating world, it will be essential to hone your detecting skills. If you have a suspicion about someone you're dating, the ten tips to the right can help you identify dishonesty from truth, fact from fiction, and paranoia from reality.

How this might appear – Couple # 4 (Ken and Jane)

Background: Ken and Jane are pretty fresh into their relationship. Ken has noticed some inconsistencies in a few stories Jane has told.

Ken: I heard you tell your friend that you took a walk yesterday afternoon.

Jane: (hesitating) Well .... yes,I did.

Ken: You told me you were at the mall all afternoon.

Jane: I was, but I took a walk after that.

Ken: Not that I care that you took a walk, I was just under the impression that you were at the mall all afternoon.

Ken eventually discovers that Jane is often leaving out pieces of information about where she says she'll be and the "walks" that she's been taking are actually rendezvous with an old boyfriend she started having feelings for again. If Ken hadn't paid attention to some small hints, he might still be strung along by Jane.



Hopefully, the information provided in this article can assist older singles in spotting a dating "red herring" that will save them much grief and heartache in the future.

We have the benefit when we're older of being "around the block a few times", but it doesn't mean we can't be duped when it comes to love.

Going slowly and cautiously into a relationship is certainly a wise move because the right relationship can provide years of love and fulfillment.


FitzMaurice, K. E. (n.d.). Communication: How to Handle Double-Bind Questions. Discover How To Choose Freedom From Ego and Improve Your Well-being. Retrieved June 3, 2013, from

Hatfield, H. (n.d.). 10 Ways to Catch a Liar. WebMD - Better information. Better health.. Retrieved June 3, 2013, from

Livermore, B. (1993, March 1). The Lessons of Love. Psychology Today. Retrieved June 3, 2013, from

Rao, M. (2010, June 9). "WHERE KNOWLEDGE IS WEALTH": “How To Identify And Manage Manipulative People?” – Prof.M.S.Rao. "WHERE KNOWLEDGE IS WEALTH". Retrieved June 3, 2013, from

Sherman, J. (2010, April 12). Doulbe Binds: A Rock and Hard Place Force Spontaneous Change. Psychology Today. Retrieved March 3, 2013, from


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