5 Lessons On Dating in Middle Age

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At age 40, my father started medical school. He’d always dreamed of becoming a doctor. Instead, he got married, had kids, became a Marine, and worked a government job.

But by the time he hit 40, he was divorced, and me and my brother were older. He decided to give his dream a shot. He got a Navy scholarship, and nearly a decade later, graduated with his medical degree.

When I hit age 40, I was divorced and re-entering the dating scene. It was both challenging and exhilarating. And my dad’s unlikely mid-life career pivot had taught me some valuable lessons.

1. It’s never too late.

Though my divorce was devastating, I gradually came to realize it wasn’t the end of my life. Rather, if I chose to see it in a certain way, it was a new beginning. So that’s the perspective I chose.

Maybe you just got your annulment decision, and you're starting to venture back into the dating scene. Maybe you’ve never been married and are still hoping to find love with someone. Either way, mid-life is not a bad place to be. On the contrary, it has many advantages.

As a young adult, you’re still navigating your way through life, and figuring out who you are, or who you want to be. By middle age, you’ve racked up some valuable life experience. You’re always going to be learning and growing, but typically you’ve been refined by your mistakes. You’re more likely to know what you want in a mate. You have knowledge of yourself and your desires that you simply didn’t possess in your 20’s and 30’s. Use that knowledge and experience.

2. It’s never too soon.

It’s wise, of course, to take time to heal and recover after a trauma like divorce, and it's necessary to go through the annulment process. And if you've never been married, it’s wise to take time to discern what you really want in a relationship, and not act too quickly. But there’s also something to be said for taking action, assuming you’re emotionally healthy. 

Scripture instructs us to “redeem the time”—or as one translation puts it: “Make the most of every opportunity” (Ephesians 5:16). Do you want to eventually get married? Then why not start now in seeking a mate? Take a risk. Go on dates. See who’s out there. If you’re too cautious or afraid, you may miss chances at finding something meaningful.

Don’t rush foolishly forward, but don’t wait forever either. Ecclesiastes 7:18 says: “It is good that you grasp one thing and also not let go of the other; for the one who fears God comes forth with both of them.” My dad could have procrastinated in pursuing his medical degree, but then he may have never fulfilled his dream of becoming a doctor.

3. It’s going to take effort.

No one becomes a doctor overnight. (If they did, I don’t want them operating on me!) In the same way, no one finds a spouse without putting in some work. You have to work on yourself, by making sure you’re healthy enough to be in a committed relationship. You also have to put forth time and effort in exploring your options, by going on dates and meeting people. Nothing worth having comes without sacrifice and effort. But, again, one advantage of dating when you’re older is that you’ve hopefully already done some of that work, so you’re a few steps ahead.

4. It’s going to take courage.

Dating at any age is a risk. You might (and probably will) get hurt. A relationship you hoped for might not work out. You may be attracted to someone who doesn’t feel the same toward you. Rejection and failure are never fun.

At the same time, you might meet someone amazing and find yourself in the kind of fulfilling relationship you always hoped for. Either way, you have to face your fears and have the courage to try. Remember the message God’s angels repeat so often in the Bible: “Don’t be afraid.”

5. It’s going to take faith in God.

My dad could have never attempted becoming a doctor in mid-life if he didn’t believe in himself. We have to believe in ourselves too. Believe that we’re capable of being in a loving relationship, that we’re worthy and have much to offer.

More importantly, though, we have to put our faith in God. We must have faith that God is going to enable us and help us in our journey (whether dating or pursuing a lifelong career dream). We have to have faith in the God who assures us that, through Him, all things are possible. That doesn’t mean we’ll always get exactly what we want. It does mean He’s exceedingly able to give us what’s best for us.

So as I continue to date in my 40’s, I’ll try to keep these lessons in mind. It’s never too late and it’s never too soon. I must be willing to put forth effort. I don’t have to be afraid. And I have a God who loves me and for whom nothing is impossible. With all those things in mind, dating in mid-life is looking pretty good.

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