Dating after 40: How to Avoid Common Pitfalls

Dating in the 21st century is so different from how it was 20 plus years ago. Most of us now have cellphones, and there are many dating apps to choose from to speed up the dating process. No more waiting at home by the corded telephone for someone to call.

There are many positives to being over 40 and dating, even in this technology-based world. Hopefully, you’ve lived and learned and built up your own financial independence. And conceivably, so have your prospective dates.

After many years of self-examination, we should know ourselves a lot better, know how to communicate our needs and wants to others, and have wisdom about what the red flags are and how to set boundaries.

Finding the best relationship for you and your future will be much easier if you avoid the common pitfalls.

1. Make sure you’re really ready to date.

After a breakup or divorce, it’s always best to wait a while to date, working through as much healing as possible—releasing all the baggage—while figuring out what you need in your life and what you don’t. Any unnecessary baggage you carry with you from your previous relationships will only ruin your current one.

Two people entering a relationship with the least amount of relationship baggage will have the healthiest start. You want to bring your most healed self to a new relationship and leave behind any feelings, good or bad, toward your exes.

If you find yourself talking mainly about ex-relationships on the first date, you probably started dating too soon. Time to go back to healing your heart before continuing with a new relationship.

Another test of readiness is your reason for seeking a new relationship. Dating just for fun or so you won’t be alone is not good for you or the other person and could lead to even more heartbreak. If you have young children, this could hurt them emotionally as well. They need stability and consistency. I always suggest children do not meet dating partners until the relationship is serious enough for marriage.

2. Trust your gut instincts.

Although some online dating statistics can be scary, many people are still using these apps and services to find lasting relationships—especially later in life. You just have to do a little more digging and trust what your instincts are telling you about each person you meet online.

Also, listen between the lines of what your new date is saying. If you feel something is not right or you are in danger, don’t ignore those feelings. God gave them to you as a warning; trust them. Ask questions, investigate, and seek safety if you need to.

Once, I was talking with a single Christian man, who told me that he pushed his ex-wife and punched her new husband during a disagreement. This was the only red flag I needed, and when he asked to meet for coffee, I kindly declined. I don’t want to get into a relationship with anyone who could have violent tendencies, especially in stressful situations. That was a deal-breaker for me, no matter the reason for his actions. I trusted my gut and probably avoided more pain and suffering in my life.

3. Have a list of deal-breakers and stick to it.

Every relationship needs to have boundaries, so it’s always best to start off by discussing exactly what you will and will not do or accept. Don't settle for less than what God wants for you.

The questions I’m often asked by women are:

  • Should I date a man who is still married but going through a divorce?
  • What if he is pressuring me to do sexual things I’m not comfortable with before marriage?

My answer is always, if that person doesn’t have integrity or feel obligated to obey God’s standards now, they won’t when they are married to you either.

Be proactive and let your date know your boundaries right up front. If they respect you, they will respect your boundaries.

A person who pushes past your need to get to know them and make decisions pleasing to God is a red flag. Don’t be afraid that you’ll lose this one person whom you like or feel that you love by enforcing boundaries. You’ll thank yourself later for holding to those standards.

4. Make sure the person you’re dating has similar moral and spiritual values.

“Do not be yoked together with unbelievers. For what do righteousness and wickedness have in common? Or what fellowship can light have with darkness?” (2 Corinthians 6:13-15)

Someone just stating that they are a Christian or go to church is not enough. You have to analyze their behaviors in order to see their heart and integrity (or lack thereof). This is also why it’s important to really get to know someone before becoming exclusive.

When I was dating in my early 20’s, if a man said he was a “Christian,” that was all I needed to hear to trust that we would have a good future together.

Throughout my marriage and divorce, I learned that there is so much more to faith than just saying you’re a Christian. There is a difference between someone who is actively following Jesus and someone who is not. Now, a deal breaker for me would be someone whose moral compass doesn’t point to the one true North.

There is a reason why the Bible commands us not to be unequally yoked with an unbeliever. We can expect a lifetime of confusion and heartache if we choose to ignore God’s standards for our lives. But we can expect a lifetime of love when we choose God’s best for us.

5. Go into dating with an open mind and an understanding heart.

Don’t take it personally if a guy you meet and see a future with doesn’t feel the same way you do. Be realistic and understand that most first dates don’t lead to a second date or end in marriage. Try to enjoy just having fun meeting lots of new people while asking God to protect your heart from further pain.

Recognize that not everyone is a good fit for you, and someone else will come along in the perfect time.

Dating is not designed to boost your self-confidence. You need to already be confident in yourself, know who you are in Christ, and have a solid support system. Then, when you are rejected (and you probably will be at some point), you’re not as deeply wounded. It will happen, so be prepared: keep your favorite self-care items handy and be hopeful in this journey of finding love.

6. Don’t rush into a new relationship or expect too much too soon.

The best relationships are built slowly over time, even if you don’t feel you have a lot of time. It may seem cliché, but fast relationships don’t last (in your years of wisdom you probably already know this). Those who rush in find themselves foolish for doing so, usually because they haven’t taken the time to really get to know the other person. If you neglect the foundation of friendship and respect, you could miss the deal-breakers. You have to build the relationship piece-by-piece, one trust-building action at a time.

Take your time, even years of getting to know each other, before you become serious. Dating is a marathon, not a sprint. The faster you try to get to the finish line (or the altar) the more damage you could do to yourself and your heart. No one wants to have repeat break-ups or divorces, so just take things slowly.

7. Don’t expect you’ll find someone soon after you start dating.

The dating pool might be smaller after 40, but that doesn’t mean it’s completely empty. If you have the mindset that no one is out there, you’ll start to believe you need to accept anyone that comes along and shows interest. Don’t be looking for perfection—that doesn’t exist—but don’t settle either.

We’re all busy working, building or rebuilding our lives, or (for some of us) raising kids, which may mean we’re not on dating websites either.

Whether you are or not, seek God's guidance to find the guy or gal you’re looking for. Although, going to church each week is a start, don’t just be there to pick up a date. Really devote yourself to worshipping God and developing a relationship with Him. Anyone worthy of your time and your heart will be attracted to that.

8. Don’t hide who you are, what you look like, or what your current situation is.

You want to put your best self forward. But make sure it’s the real you, not just something you think the opposite sex will be impressed with.

So many people on dating websites are actually still legally married to other people—trust me, I’ve looked. It may be what everyone else is doing or what others are telling you to do, but if you’re still married, do the right thing and maintain the integrity of your marriage: wait until the divorce is completely finalized. After a time of healing, then you can start looking.

Whether you have one child or eight, be honest with that information right up front. Some people love children and want a big family, so they won’t be intimidated by your family size. But not everyone. Giving someone who is not interested in raising children a chance to walk away will protect all involoved from unnecessary hurt. And honestly, no one wants to be lied to—that would be a deal breaker.

Only post updated photos of yourself: nothing with your children or any ex-relationships (even if that person is cropped out). 

Lastly, don’t share cleavage, muscle, or other body parts in your photos hoping to attract a new mate. You want someone who accepts you, the good and the bad, without seeing you as a trophy or a body (to be used). You are so much more than your physical attributes. Share your talents and personality. The right person will be impressed by what you truly look like and who you really are rather than some made up, fake version of yourself. If you have high standards for yourself, you’ll attract someone who also has high standards.

9. Don’t skip getting to know the other person’s family and friends early in the relationship.

We can really learn a lot about someone by how they treat their family and friends—especially in stressful situations. Do they even have long-term friendships? Will they allow you to talk to these people in private without them there? If they’re divorced, can you speak to their ex-spouse to find out the whole story? How do they behave around these people? And do they have appropriate boundaries while being kind and assertive, or are they passive-aggressive and mean, blaming the other people for how they behave?

Also, what truly is their relationship with Christ? Is He their Savior whom they depend on daily? Or is this an act just to impress you?

These are the questions you need to be asking yourself as you get to know someone you want to date or be serious with. It takes time, so don’t rush it. Skipping this step could mean missing many serious red flags while dating.

10. Don’t expect all people to be the same.

A part of healing after heartbreak is not associating all men or all women with the person who broke your heart. A few bad apples in a bunch doesn’t mean they’re all bad. It’s only through deep heart healing and getting to know new people that we start to see that not every man or woman is exactly the same. And even someone with similar qualities can be a totally different person.

Furthermore, you may have a hard time trusting new people and may be cautious because of your past experiences, which is normal. But you can allow yourself to give and receive love in new and healthy relationships. You can be cautious while still allowing yourself to trust other people again. God is love. When you love God and His people, love will find you too. Hold onto hope!

Life is not over after long-term singleness, a break-up, or divorce, even in your 40’s. You just need to plan your course of action while being open to the direction that God will take you. Trust His will for your life. 

Jen Grice is a Christian Divorce Mentor and Empowerment Coach, author of the book, You Can Survive Divorce: Hope, Healing, and Encouragement for Your Journey, a speaker, and a single homeschooling mom. She writes full-time at and empowers women to survive and heal after their unwanted divorce on her YouTube channel as well. Jen believes that through God's healing, grace, and redemption that all Christian women can survive... and even thrive, after divorce. 


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