Dating When You're Older: What to Consider

Do people over the age of 40 have the same concerns about dating as those who are younger?

Yes. BUT, those dating later in life have additional concerns that most 20 somethings do not. Let me explain.

All individuals who date should know that there are two powerful emotions that can blur one's ability to see clearly or mask that which is really happening. The first emotion is infatuation, and the second is the fear of being alone. Both of these sentiments can derail the development of a solid and lasting relationship because both can hijack the ability to reason and be logical. Both can up-sale romance, downplay reality, and result in very poor decision making.

To date successfully, you must reign in the intoxication associated with falling in love or the fear of living alone no matter your age.

But, if you are older, you have to pay attention to other considerations because you have had more life experiences and have worked longer. People approaching 40 or older tend to have pensions, investments, and retirement plans. They tend to own property, recreational equipment, and other material goods. Most have children or grandchildren. And, most have experienced at least one committed intimate relationship.

These additional factors complicate the dating scene and have to be investigated.

Let me share a story to illustrate this point. A widow called to tell me that her husband of nearly 25 years died after a long debilitating illness. Six months after his death, a friend suggested she try a dating app. She uploaded her profile and immediately found that several men in her area wanted to meet her. With the help of her friend, she selected three men on the list to contact. Two of the three were so so. But, the third one stirred her emotions to a point that she lost her mind along with her heart.

Let's cut to the chase. This woman let infatuation and fear of living alone cloud her judgment. By her own admission, she trusted too early. She assumed the best without scrutiny. She overlooked the fact that her new man had been married three times before. She paid no attention when his children and extended family asked for financial support. She disregarded feedback from her own children and extended family that he might be gaslighting her. She overlooked it all.

Within a year, she married him and life was pleasant—until it wasn't.

Around their first anniversary, she noticed changes in his personality that impacted his ability to work and be happy. He isolated himself and became depressed. Despite her concerns and attempts to lean in, he continued to pull away. Months later, suicidal ideations appeared. And within a few more weeks, she became a widow again.

After hearing her story, I asked, "what advice would you give to people your age who want to date with the intention of remarrying?" She gave me these answers without hesitation. And, while everyone's situations and relationships are unique and these pieces of advice don't apply to everyone's story...they are definitely worth pondering.

If you're wanting to marry later in life, first consider the following...

You have to investigate every aspect of the other's life. Leave no stone unturned. She said that she didn't ask any tough questions or challenge anything that he said. She blindly accepted everything without scrutiny.

Do not move forward if the other always agrees with you and never challenges you on tough issues. When she looks back, she realizes that he never asked her tough questions. He always made her feel like she was perfect. In fact, she sometimes felt his affirmations were baseless and shallow. Yet, she didn't question him.

If the other has been married before, talk with the previous spouse or spouses. She truly regrets that she never called the man's previous spouses to see why they divorced. If she had, the women would have told her that he was clinically depressed and had attempted suicide previously.

Ask about finances, investments, debt, and pensions. This may seem very invasive and off-putting, but a talk about each other's material gains or losses has to happen. One's management of earthly goods provides a deep dive into what that person holds dear or disregards.

Do not get engaged hastily. The woman told me that she wished she would have waited longer to get engaged because just over a year with this man, she found that her emotions for him were waning. Infatuation was less intense and her fear of being alone was quelled. That is when her perspective became more logical. But, by that time, she was into making wedding plans and didn't want to stop the process.