Shocking Dating Lessons from My Very Good Friend Ron

I’ve written before about my friend Ron’s dating escapades. He’s now in his 60s, and it’s been quite eye-opening to reenter the world of dating after a marriage of over 30 years.

At the advice of his kids, Ron signed up for Match.com after his divorce was final a few years ago. There he quickly found a Christian woman named Sherry, whose favorite books were Rick Warren’s Purpose Driven Life and Living Courageously by Joyce Meyer.

“This is my kind of woman!” Ron confidently told me before his coffee date with her at Panera Bread.

But things didn’t exactly go as he had hoped. The first thing he noticed was that Sherry looked at least 10 years older than the pictures she had posted. Hmmm…pretty disappointing, he immediately thought.

However, Ron is a nice guy, and he decided to at least engage Sherry in some friendly conversation. After some small talk, he asked, “So, how long ago was your divorce?”

Ron thought this was a pretty easy, straightforward question. But her answer stunned him.

“Well, I’ve been married four times,” Sherry informed him, “and for a while I also lived with a guy I wasn’t married to.”

Ron’s jaw probably dropped at this point. But she went on to say she had eight children and fifteen grandkids, attributable to her various marriages and boyfriends.

Yikes, Ron was getting queasy. How did things go so amiss in his attempt to find a wholesome Christian woman? While the conversation was running its course, he couldn’t help envisioning Thanksgiving dinner if he married Sherry. How would he be able to figure out “who’s who” among the kids and grandkids—not to mention remembering who everyone’s daddy is?

This was a rough start to his online dating experiences, no doubt. Yet Ron wasn’t about to give up. He continued spending time on Match.com every day, trying to find suitable prospects for dating and eventual marriage.

Uncomfortable Encounters

Things didn’t get any easier in the following months, though. One day he was having a nice phone conversation with a woman named Sarah, and they seemed to have some things in common. But he started getting uncomfortable when she mentioned her distress that her son was gay and had married his lover. Once again, Ron started envisioning Thanksgiving dinner, and he wasn’t sure how he would respond to the family dynamics of Sarah’s son and the guy he was married to.

Then he had another coffee date, this time with an attractive woman named Sheila. But her husband had died of HIV, her father had been shot to death and, once again, Ron felt there was just too much baggage for him handle.

Ron says one of his favorite dates was with a woman named Linda. She attended a good church and clearly had a strong relationship with the Lord. But the conversation took a difficult turn when she described her daughter’s bipolar personality disorder and the incredible anguish it had caused her. Some days her daughter loved her, and other days her daughter hated her, making Linda’s life miserable.

Another disappointing date occurred when Ron went out to dinner with a woman named Sarah. She had been a single mom for many years and was now agonizing that her 16-year-old son had become a neo-Nazi skinhead, hating Jews and believing all sorts of conspiracy theories. She had no idea how to convince the young man of his erroneous views—and neither did Ron.

5 Lessons

Eventually Ron had some relationships that were more than a one-time phone call, coffee date, or dinner. He says some of these were with very nice women, but he just couldn’t see himself spending the rest of his life with them.

Recently Ron and I took time to review his dating experiences, hoping to glean lessons for others entering the dating scene in their 50s and 60s. Here are five lessons we came up with, but perhaps you can add some insights from your own experiences:

  1. Dishonesty is rampant. While it’s understandable to “put your best foot forward,” it’s sad there are so many outdated pictures and misleading online profiles. Also watch out for the out-and-out scams that target online daters. Despite your hopes for “love at first sight,” be careful to verify that the person you’re dating is who they say they are!
  2. Baggage is rampant. Ron chuckled that many woman on Match.com describe themselves as “baggage free” and “drama free.” What a joke. He concluded that it’s virtually impossible to be a divorced person in your 50s or 60s without accumulating some baggage along the way.
  3. Our OWN baggage is rampant. Like many men, Ron initially thought all the baggage was on the female  side of things. Yet after some painful breakups, he had to admit that his own baggage was often a large part of the problem. Just like landmines under the surface of the ground, he discovered emotional scars that were triggered in pressure situations and close relationships.
  4. Sexual temptation is rampant. Ron was a virgin when he got married, but he admits that sexual abstinence is a lot harder these days. Perhaps this can be attributed to several factors: (1) Loneliness in being single after many years of marriage; (2) feeling like “time is running out” to have a close, intimate relationship; (3) the amazing willingness today of many women (even longtime Christian women) to engage in sexual activities with men they aren’t married to.
  5. Not everyone really wants to be married again. At the beginning of his online dating journey, Ron assumed anyone on Match.com or eHarmony was there in search of a marriage partner. Surprisingly, it turned out that many people were more interested in dating than marrying. Why so? Some are fearful. No one wants to enter into another unhappy marriage. And some prefer the freedom of not having to answer to anyone. Instead of being tied down, they would prefer to “keep their options open.” And, once again, Ron had to come to grips with his own commitment phobia. “I have a pretty good life as a single guy,” he told me. “Why run the risk of another bad marriage?”

What About You?

If you’re in the dating world today, my heart goes out to you. I sincerely hope you’ve had an easier time than my good friend Ron.

Although I could attempt to provide all sorts of spiritual platitudes and additional advice, let me close with just a simple reminder from Scripture:

Trust in the Lord with all your heart,
And lean not on your own understanding;
In all your ways acknowledge Him,
And He shall direct your paths
(Proverbs 3:5-6).

I wish you well on this perilous journey!

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So, What Are You Afraid Of?

When my friend Jacob recently entered the world of online dating, he found it to be a terrifying experience.

“Jim,” he confided, “you wouldn’t believe how different the dating scene is than when I was in my twenties.”

Jacob’s marriage of 30+ years had ended several months before, and now he was embarking on a mission he never expected: the search for a new wife.

Sensing his discomfort with the whole situation, I asked, “What are you so afraid of? Why don’t you just relax and enjoy the ride?”

“That’s easy for you to say,” he replied. “You just don’t understand…”

“OK, explain it to me then. What exactly is so terrifying about meeting new people and going on dates?”

Lots of things are terrifying!” Jacob said, clearly irritated that he had to spell things out for me. “Some days I’m afraid I’ll never find the woman of my dreams. Other days I’m afraid I will find the woman of my dreams, but I’ll mess things up and she won’t love me in return.”

“Sounds like a real dilemma,” I acknowledged.

As our conversation continued, it became clear that my friend was still hurting from his unhappy marriage and the rejection he felt when his wife left him. But I encouraged him that God had a plan and he shouldn’t give up.

“You’re still dealing with the grieving process, Jacob. That’s normal after what you’ve gone through, but as you trust the Lord in this, I know He will keep working to heal your heart.”

Just a few weeks later, Jacob called to say that my prayers for him must be working.

“Jim, I’m so excited. I found this amazing woman on Match.com, and she has agreed to meet me for coffee tonight.”

I told Jacob I was happy for him and asked him to let me know how things went on his big date.

Sure enough, my friend called on the way home from meeting this beautiful and successful woman he had found online.

“We talked for nearly two hours,” Jacob gushed. “It was going really well until we got to the part where we asked each other what we’re looking for in a partner.”

“That sounds like a fair question. So what did you tell her?”

Apparently Jacob gave this lovely woman a lengthy description of how he wanted someone faithful and kind…affectionate…loving unconditionally…never holding a grudge…grateful for the little things in life…and always glad to see him.

To his horror, she replied somewhat indignantly to his wish list, “It sounds like what you really need is a DOG!”

After I got done laughing at my friend’s plight, we ended up discussing the many benefits of having a dog while going through life’s transitions.

“You’ve got to admit, Jacob, dogs can be pretty cool. They’re low maintenance, easy to please, and they lick your face for no reason at all…”

Well, I probably shouldn’t have laughed at my friend’s anguish. But Jacob’s online dating experiences have given us some good opportunities to discuss two universal forces in life: FEAR and FAITH.

On the one hand, the Bible assures us that God hasn’t given us a spirit of fear (2 Timothy 1:7). However, that certainly doesn’t mean He won’t place us in scary situations from time to time.

Remember the shepherds in the Christmas story? (Luke 2:8-20) They were just minding their business one dark night when “an angel of the Lord” woke them up with a terrifying divine encounter.

The shepherds’ experience follows a pattern found throughout the Bible: First, God puts us in circumstances that cause our fears to rise, and then He comforts those fears by telling us, “Do not be afraid” (v. 10).

Isn’t that pretty funny?

Jacob and I have concluded that fearful circumstances are simply part of God’s healing process to REVEAL and then HEAL us of our fears. It’s all part of His love for us and His determination to uproot anything that’s keeping us from His BEST for our lives.

So the next time you sense fear rising in your heart, don’t shy away from it. Face it head on and recognize it for what it is: God’s plan to set you free from fear so you can enter into His highest purposes for your life.

Remember how the Israelites cowered in fear on the brink of their Promised Land (Numbers 13)? They didn’t realize it at the time, but their FEARS were actually pointing the way toward their FUTURE. Unnecessarily, they spent 40 years in the wilderness before they were willing to confront the fear and unbelief lurking in their hearts.

So, what are YOU afraid of today? It’s probably a clue to an important breakthrough God wants to give you in some area of your life.

Yes, you may want to get a dog too. But that’s only a temporary solution.

 

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