Dating After Divorce – The Good, the Bad, and the Ugly

If you play your cards right, dating after divorce can be both an exciting and a deeply fulfilling experience. But the post-divorce dating landscape is also riddled with potholes and landmines.

In this article, I’ll outline a wide spectrum of issues you might encounter when dating following divorce. These situations and scenarios range from the very good to the very bad, with a few in between.

Part of winning the post-divorce dating game is being prepared. And if you’re as old as I am, time is of the essence. Becoming successful at dating through trial and error is silly and time-consuming.

Join me as I get you up to speed on what to expect (and what to avoid) as a second-time bachelor in the new technological age of dating. In this way, you can maximize your efforts and avoid the most common mistakes men make when dating post-divorce.

We’ll work our way from the ugly to the bad to the good. So first, the bad news.

The Ugly – Dating before you’re ready

The vast majority of post-divorce dating disasters are the result of entering the dating pool before you’re mentally equipped to do so. But how do you know if you’re ready? Read my article on how long you should wait to start dating after divorce if you’re looking for an in-depth discussion.

The short answer is that it takes some time to completely heal from the physical, emotional, and financial turmoil of a divorce. Pursuing relationships for the wrong reasons is a recipe for disaster for men who are already mentally exhausted from divorce.

If any of the following scenarios sounds familiar, then chances are you aren’t quite ready to date.

Dating as a means to get back at your ex-wife

If you’re considering dating as a means to exact revenge on your ex, dating should be the last thing on your mind. You definitely need more time to process your emotions and leave bitterness behind.

If you’ve truly moved on, your goal should be that your ex-wife never knows about your love life. Your ex only truly needs to know about your romantic interests when it affects her directly. For instance, when you’re in a committed relationship with a new woman who will interact with your children.

I cover this important concept and others in my single dad’s guide to dating with children.

Shopping for a replacement for your ex-wife

For many men, divorce wasn’t their choice. As a matter of fact, some studies have suggested that women initiate divorce as much as 70% of the time.

Some men think that dating will make them forget their ex-wife. But they inevitably end up comparing every woman they date to their ex.

Wait until you’re mentally prepared to appreciate a new woman as a unique individual before you consider dating.

The dreaded “rebound relationship”

Nothing throws up a red flag faster than entering into a serious relationship right after your divorce. This situation is commonly known as a rebound relationship and could involve one or even two individuals that recently ended a long term relationship.

A rebound relationship is entered into immediately after another has ended, leaving that person vulnerable. It manifests because one or more of the participants find the other fills some void created or exposed through their previous relationship.

Frequently these relationships start strong, even though other aspects of this new relationship suggest obvious incompatibilities. However, they often burn out just as fast. Do your best to avoid relationships altogether for at least six months once you start dating.

After a divorce you should raise, not lower, your standards

Just because you’re divorced doesn’t mean you have to stop being selective. If anything you should be even pickier since you didn’t choose wisely the first time around.

There are plenty of single women in the dating pool looking for a man just like you. At last count, there are 3.52 billion women on the planet Earth. So why throw yourself at the first one who seems interested?

Odds are you’ll go on more than a few dates with many different women before you find one who is compatible enough to pursue something further.

If you’re mentally ready to date, and you’ve still come up empty when pursuing women, maybe try widening your net. Consider joining an online dating site where the women are plentiful and actively looking for single men like yourself.

Check out my review for divorcees for an extensive run-down of what Match has to offer.

The Bad – Modern dating requires patience and endurance

Thanks to advances in dating technology, you no longer have to be a pick-up artist to land incredible dates with the most desirable women on the market. Due in large part to online dating sites and apps, meeting new women is much easier than it used to be.

But window shopping for dates isn’t without its drawbacks.

Superficiality is alive and well

Although online dating is an excellent way to get back onto the dating scene, the sheer volume of options means people get rejected for silly and shallow reasons. And this behavior isn’t limited to men, both sexes are equally superficial.

She’s a little plump… Next! I don’t know about that hairstyle… Next! That pink shirt puts me off… Next!

But sometimes attraction has as much to do with personality as it does with appearance. This means using apps like Tinder which put attraction front and center could mean missed opportunities with highly compatible women.

Sites like Tinder and Bumble only give you a small glimpse into a woman’s personality. This means you simply have to go on more, but frequently unsuccessful dates to determine compatibility.

These are the known drawbacks of free dating apps.

More dates means more rejection

With the increased number of dates that modern dating demands, it follows that many dates will end without a connection forming. Getting accustomed to frequent rejection (and lots of it) is one of the most challenging obstacles to overcome post-divorce. It’s easy to get jaded if you don’t have one or two quick successes.

Through my experiences with many different dating services, I learned that online dating is one of the least-painful training grounds for rejection.


Because even the most attractive men will face countless unanswered messages, date cancellations, and general flakiness.

The upside?

Rejection is quick, sometimes comical, and more time than not requires very little up-front investment. Before you know it, rejection (and ghosting as the kids are calling it), will roll off of your back without much thought.

The Good – You’re wiser and your younger competition is outmatched

If you were married for any significant amount of time, you likely experienced the joys of traditional dating. You know, back in the day when you had to woo a woman with dinners and charm in order to get her into the sack?

As it turns out, those interpersonal skills are severely lacking among men in the age of online dating. I can’t tell you how many women mentioned how impressed they were that I had even basic manners on our date. I’m not talking about opening car doors or putting my jacket in a water puddle for her to walk over, more like just being a gentleman.

So, although you may think you’re starting at a disadvantage when reentering the dating pool after divorce, nothing could be further from the truth. The skills you learned in traditional dating will give you a decisive edge over the countless douchebags the frequent many of the online dating sites.

Here are some other positive developments that you can expect when dating after divorce.

Knowing what doesn’t work, you’re a step closer to knowing what does work

Thomas Edison’s light bulb experiments taught him endless ways NOT to make a lightbulb. Your unsuccessful marriage has probably taught you more than a few things that are now deal-breakers in a new partner.

As Edison found, knowing what doesn’t work brings you one step closer to finding something that does. The key is leveraging the life lessons you’ve learned and avoiding committing the same mistakes again.

Thanks to online dating, you have more choices than ever

Back in the day, your circle of friends and acquaintances contained all the women you were likely to meet and possibly date. Online dating allows you to connect with women that you otherwise would have never had an opportunity to meet.

Modern dating profiles provide accurate indicators of compatibility. These indicators allow you to eliminate women with deal-breakers- things you might have only learned about them after a few dates. Instead, you can focus your time (and money) on the countless women that have real potential.

Rebuilding your self-image is a humbling but rewarding experience

A bad marriage and subsequent divorce can be both emotionally traumatic and financially draining. The experience can literally kill your ego. It’s easy to forget that you are the same intelligent, funny, and desirable man that you always were.

While marriage may have left you questioning your value on the open market, dating after divorce will remind you that you’re still a marketable commodity. If you work on yourself first, then put your best foot forward, there are women out there who will appreciate what you have to offer.

Dating will re-ignite emotions you forgot you ever had

Ok, so you can’t become a teenager again, even if you might feel like one at times. But who wants to be a teenager anyway? Acne, angst, and drama are things better left in the past.

But there is no denying that some of the emotions you experienced as a young adult will come rushing back when you begin dating after your divorce. Pre-date butterflies, the anxiety of wondering if your interest in a woman is reciprocated, the crushing agony of rejection- these are real emotions that you likely forgot you had.

This has been one of the most rewarding experiences for me (rejection and all), something that I totally didn’t expect coming out of my marriage. Before I began dating again, I was convinced that my bad marriage had completely numbed my emotions.

But I was thrilled to learn that this couldn’t be further from the truth. I’ve also found that being older and going through a divorce helped me to process these emotions maturely, good or bad.

For me, experiencing negative or even painful emotions is light-years better than experiencing no emotions at all. It’s good to feel again.

The good aspects of dating after divorce eclipse the bad and ugly

In my experience with dating after divorce, the good has far outweighed both the bad and the ugly. I am happy to report that finding dates is much easier than it used to be and the entire experience is more enjoyable.

But before I started dating, I worked on myself and made sure that I was in the right head-space to start this new journey. Subsequently, I was well-equipped to successfully pursue promising opportunities when they presented themselves.

If you enter the post-divorce dating world after you’ve had ample time to get your own life in order, I truly believe that you’ll thrive in the new and improved dating world.

The 10 Legal Documents you Must Address After Divorce
The divorce is final and you begin to breathe a sigh of relief. Finally, the red tape is cleared, the

Column 2