Too Good To Be True: Essential Lessons on Dating After Divorce

Have you ever found yourself in a situation where you realize that something wasn't right? You can feel it in your gut. The difficult thing here is there's nothing wrong. In fact, everything is great. Maybe everything is too good.

This is exactly the situation that a guy I talked to recently found himself in. His name is Joe. He was married twice for a total of 40 years, divorced for two years. Joe called me up and we talked for about an hour a few days ago, and his experience was that things seemed to be a little too good to be true.

It didn't take long in our conversation when it became really clear what Joe was experiencing. So I thought I'd share this experience with you. I figure it's a good story, and there's probably something in it for you.

The Addiction to Having a Woman in Your Life

After 40 years of being married to two different women—one for 25 years, the other for about 15—Joe found himself single. Being married for that period of time creates habits, and these habits can almost be likened to an addiction of having a woman in your life.

I think this happens to a lot of guys where just having the presence of another person, specifically a woman who's occupying space in your life, becomes something that you become accustomed to. It's just part of life.

Despite watching a lot of my videos and buying into the whole Life 2.0 philosophy—autonomy and authenticity and all that stuff—Joe couldn't help himself. He got on the apps. He didn't want to. He told me he resisted it, but he just had to check it out. It's like he just had to see behind the curtain to see what was going on back there.

The Reality of Dating Over 50

Well, Joe discovered that there are a lot of single women in his age group (he's about 65), women in their 50s and early 60s, who are very interested in a single man of his stature and age.

Now, Joe's not super rich, but he's got a decent lifestyle. He's financially fine. He's in good shape. He's a decent-looking guy—an average guy, but certainly decent-looking. He seemed normal to me. But to these women? He might as well have been George Clooney because they were coming after him.

From the moment I started talking to Joe, I picked up on his vibe, and it was like a kid in a toy store with an unlimited budget. He's got the credit card and can get anything he wants—that's the energy he was giving off.

The Flip Script of Modern Dating

This is the flipped script narrative of modern dating, where suddenly guys go from being the pursuers to being the pursued, even the average guys. Obviously, there's that top 10% of guys that are always going to be pursued from the time they're teenagers. But there's a time when you get to be in your 50s and 60s, where suddenly you get the chance to see what it's like to be a Chad.

You've got all these divorced women out there, and they're realizing that life isn't as good as they thought it was going to be. They need a man for a security blanket. They need to feel safe, loved, and appreciated. They need someone to talk to.

The value of a single man in his 50s or 60s, especially one who's financially independent, has his own home, and has passive income? These guys are pure gold. You've gone from being an average guy—a five or a six—to now you are a 10 because they are going to target you.

Joe's Complicated Situation

Joe had a lot of complexities to his situation. First, his ex-wife recently paid a visit to his place. While she's there, the unthinkable happens—they hook up. Joe wasn't expecting this. She left him, though he wasn't necessarily unhappy about it. But having the opportunity to rekindle something seemed interesting to him.

His experience on the dating apps was even more interesting. He had to travel to meet up with a woman from the app. Joe got a hotel so he could stay the night, and that date ended up back in the hotel room. Joe didn't seal the deal on this one—there was no absolute hookup—but there was a lot of physical connection going on.

So Joe is getting more action now than he's gotten in at least 10 years. He's thinking he's falling in shit and coming out smelling like a rose. He can't figure out what the hell's going on or how this is happening to him. And he's got two or three other women on the line on the dating apps that he's communicating with and making plans with.

The Cautionary Tale of the Ex-Wife

The first woman who recognized Joe's value, ironically enough, was his ex-wife. Joe started getting ideas about this, asking me, "All women are going to have some kind of baggage. Isn't it better to go with the baggage you know than the baggage you don't?"

I understand the logic. I've had that thought myself. In the final stages of my relationship with my ex-wife, I remember thinking, "I've got to go out and meet new women now. I'm going to have to deal with all their baggage. I know the baggage she has. I can deal with that."

But here's the cautionary tale: She made a conscious decision to leave you. What makes you think that she has changed so much that now she sees you with new eyes?

When I asked Joe if she had addressed some of the problems they had, he said she was pretty much the same way as before. That tells you all you need to know. She hasn't progressed. She hasn't moved on. She hasn't changed.

All that's happened is she's realized that now she's alone. She's got to pay all her own bills. She doesn't have a man to keep her secure and safe. And you're the best option she has.

It's not like she's had a come-to-Jesus moment where she thought, "Oh my gosh, I've made such a huge error. I need to change my ways and become a better person." She's experiencing loneliness and maybe some financial hardship, so she's seeing you as a body with money that she can use.

Don't fall for it. It's a fool's game.

Essential Boundaries for Dating Success

When it comes to dating at this stage in the game, if you're in your 40s, 50s, or 60s and you've been divorced, you have turned yourself into a high-value man. You are in demand. You are now the prize, and she is now the pursuer.

Do not let her pretend that you need to pursue her because you don't. Trust me, she's coming hard for you whether you realize it or not.

Here are the essential boundaries I told Joe he needed:

1. Create Your Lists

Make a list of all the characteristics you're looking for in a partner. Also, make a list of all the negative things that you absolutely will not put up with—deal breakers. If she's got one of these red flags, you're pulling the rip cord. It's done.

2. Set Time Boundaries

Get really clear about how far these relationships will go. Don't allow yourself to make a long-term commitment until you've been dating a woman for at least a year or two.

3. Keep Family Separate

For the first six months of any relationship, keep your family out of it. Don't bring your kids into it. Don't bring her to birthday parties or family functions. Keep these two worlds separate until you become really clear what she means to you.

4. The 3-Month Rule

No sex for at least 3 months, maybe even longer. This is crucial. If you've been through bad marriages, probably the intimacy and thinking with your small head allowed you to get into situations that your big head would have kept you out of.

By creating this boundary, you get the opportunity to experience this person in a platonic relationship. You can build sexual tension during this time, but you disarm her weapon. She can't pull out sex whenever she wants to try to trap you.

The minute you start having sex, the fog of intimacy will blur your vision to what's really happening. You can't see the red flags when you're wearing rose-colored glasses.

5. Keep Finances Separate

You don't need to meet a woman who's completely financially perfect, but you definitely don't want to find a woman who's financially needy and needs your financial support to make ends meet. This is a trap. You can never trust that she's actually interested in you—she may just be interested in your wallet.

6. Consider Friends with Benefits

I strongly recommend that you do not cohabitate with a woman. Maintaining your autonomy so that you can live from an authentic perspective is what makes you attractive to these women. Once you submit to them, you give up your autonomy on some level.

To keep the relationship fresh, have romantic interludes, dates, sleepovers, and go out together for fun, yet you both have your own place to retreat to and your own privacy.

The Terror of Authenticity

I think the problem Joe is having underneath it all is the addiction to having a woman in his life, but also there's a little bit of terror that we experience when we're confronted with both the opportunity and the almost obligation to live our lives from an authentic perspective and to be completely autonomous.

If you've been in a relationship for a very long time, you've always been checking in. You've always had this other voice in your head. Once that voice is gone and the only voice you hear is your own, it can freak guys out.

Giving yourself the time to get accustomed to being single—and this can take years—is really the critical part here. You've got to get accustomed to hearing just your voice in your head and honoring that voice and following it to the places you want to go.

The Bottom Line

Joe is only out of a marriage for two years and already reconnecting with his ex-wife. I think Joe needs to spend more time on his own. He needs to get accustomed to what this whole experience is really about. He needs to embrace his own authenticity and autonomy and enjoy that.

It's hard at first, but once you get into the rhythm of it, you will never trade it for anything. You'll guard it jealously.

The biggest mistake that leads to second marriages is jumping back in before you're ready. That's why the divorce rate for second marriages is worse than first marriages.

Don't do that to yourself.

If you're a man in your 30s, 40s, 50s, or 60s who's suddenly single, take the time to understand your new position in the dating market. You have more power than you realize—but with that power comes the responsibility to use it wisely.

Stay healthy, and if you can, stay single.

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