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Dating After Divorce

Tips from a dating coach: How to be single after a long relationship and how to move on after divorce

Dating After Divorce

Here's some advice on dating after divorce.

It’s been said that divorce is like construction: It always takes longer and costs more than you predicted.

Add to that the sheer trauma of untying the knot. Take it from a dating coach who has been divorced: It’s one of the most excruciating experiences a man can endure. One client of mine compared his divorce to the death of a loved one because he not only lost a close relationship, but it also impacted his family connections in profound, painful ways.

There’s also the division of assets and property, the pain that children endure, and the intense emotional torment both sides feel. Divorce is a singularly traumatizing experience.

“It’s ripping your heart out through your wallet,” Robin Williams once said.

man and woman hugging

Dating after divorce. It sounds scary. The thought of how to move on after divorce is intimidating. But it’s a specialty of mine. I’m a dating coach, yes, but I’m also a therapist, of sorts. I’ve helped many divorced men attract amazing women, and to find the RIGHT woman to eventually settle down with.

I’ve noticed another consequence of the death of a marriage: the effects it has on a guy’s identity. After all, who a man is can be tied to who he married.

If you’re newly divorced, you may be thinking, “If I’m not a husband, then who am I?”

When you combine a loss of identity with financial and emotional trauma—not to mention loneliness—some men take drastic measures and hurt themselves.  According to reseach from a University of California sociologist, men who are either divorced or separated are twice as likely to commit suicide as married men are.

Now, if you’re divorced or separated, you’ve likely had friends and family say, “Now you can get out there and date and meet someone new.”

But if you’re anything like me after my marriage ended, a little voice is whispering…

“Beautiful women don’t want some older, divorced guy.”

“I’m just not attractive—I’m past my prime.”

“I forgot how to date.”

“All these apps are so confusing. It’s overwhelming. I can’t do it.”

I totally get it. Any of those thoughts are understandable.

And they’re 100 percent WRONG.

I proved that to myself. After I got divorced, I went on a mission to learn how to attract women as my authentic self, so that I could choose my next long-term relationship, and not feel I had to settle.  

man waiting - dating after divorce

And now my favorite kind of client? A guy who is single and who WANTS to mingle—but he’s battling self-doubt.

Why Is Dating After Divorce So Hard?

Dating after divorce is so difficult because not only are you dealing with feelings of pain, anger, and grief, but you are bringing different expectations of relationships to the table. You may struggle with trust, if there are kids in the mix you might worry how they may react, and your self-esteem may have taken a hit. But it is possible to learn how to start dating again and accept it as a new journey.

How To Date After Divorce As A Man

My client James, 54, came to me interested in dating after divorce. He didn’t know how to be single after a long relationship. The owner of a small consulting business in the New York City area, James was plagued by fear, frustration and doubt. He’d endured a brutal, bitter, years-long separation and divorce that damaged his relationship with his teenage daughters.

And he was rusty. When we met, James hadn’t been out on a date since the Clinton Administration.

“My divorce took three long years and it left me feeling empty,” James said. “I wanted to date again, but I just felt small and weak. Being told by your ex-wife and your daughters that you’re a terrible guy, well, it crushes you. I was not high in confidence. I tried Tinder for a while but didn’t get many matches, and when I did get a date, I didn’t know how to flirt and connect. I felt too old and ugly for the kinds of women I was attracted to.”

James and I got to work. First, we completely rebuilt his confidence—in less than a week. You see, success with women is 80 percent psychology, 20 percent technique. The best pickup line on the planet won’t work if you feel unworthy and unattractive.  

Then, with his newfound confidence and self-belief, James learned my simple system for meeting and attracting women in upscale bars and lounges. We also overhauled his approach to Tinder and online-dating. He soon woke up daily with 3 to 5 new matches.

The night it all came together? It was only his second night out meeting women since the 1990s. “I was at a rooftop lounge, and I approached this beautiful, classy Latina in a red dress,” James said. “We had instant chemistry, and I knew exactly what to say and how to connect. She’s 29 and I’m 54. We were all over each other, and I thought, ‘Wow, I’m 25 years older than her! I felt so confident, attractive, and myself.”

dating after divorce - with woman

I was with James that night, and I can tell you this: If you want to know how to move on after divorce, a great way to start is approaching a gorgeous Latina, connecting, making out with her, and setting up a date.

As I write these words, James is dating three beautiful women, including a model-turned-photographer who he met on Tinder. He said he wants to play the field before settling down with a new a girlfriend and then, when he’s ready, get remarried.

“It feels incredible having the choice and freedom to date new women, to do it as myself, and to know that I’m still attractive.” He laughed. “VERY attractive. I’m dating a model! I feel like a bad-ass alpha male. I’m a new man. I can’t believe this is my life.”

How To Be Single After A Long Relationship

Being single may feel like a curse initially. Maybe you've told yourself you're too old or there aren't enough fish in the sea because the good ones are already married. But those are just excuses and not truths. Embrace single life. See it for what it is: an amazing opportunity.

Now, not every single guy wants to date three women at once, but every single guy wants options. Whether you are just wanting to date again, or are trying to find the new woman of your dreams to settle down with, this is a new opportunity for something fantastic to enter your life.

My main message for you: YOU have options. You might not know how attractive you are. You might not know how many women would love to meet a cool, experienced man who’s lived a life, had experiences—divorce among them.

It may not feel this way now, but you can learn to attract amazing women, and you can change how you feel inside.

And take it from a fellow divorced dude: the end of your marriage was a GOOD thing. Its end has created space for something great.

You can write a new chapter. You have the skills to attract incredible women, even if you’re carrying extra pounds, or feeling like you’re past your prime.

You can move into a new prime. Your late prime.

When my wife left me, I thought I would end up alone. I’ve since gone on to date the most wonderful, beautiful women. I can connect the dots—from loading up my red Honda Civic and driving out of my ex’s life, to becoming great with women, to becoming a dating coach who helps men attract amazing women.

When James and his wife split up, he said he felt “worthless” inside. And he’s now dating three sexy, classy women—and he feels more significant as a man.

You are capable of the same kind of transformation.

Finding Happiness in Remarrying

holding hands - dating coach

If you want to date again, you may one day want to marry again, too. One-third of divorced men remarry, compared to just a quarter of divorced women.

If you decide down the road to tie the knot again, research shows that you’ll be happier and richer. According to the Institute of Family Studies, married men are healthier, wealthier and have better sex than most single guys.  

Now, there’s no hurry. You probably won’t be swiping on Tinder the same day your divorce papers are finalized. But when you’re ready to start dating again, get excited about the prospect of finding a NEW someone to share your life with.

And remember: Those feelings of being “not enough” or “too old” are lies your mind tells you. In order to move on after divorce, you need to get this.

You are MORE than enough. In fact, divorced men have HUGE advantages in the dating game. Guys who were married are more selective, and women want to date selective men. Also, if you have kids, know that there are a lot of single women who have children of their own. Guys without kids tend to treat single moms like they’re radioactive, so these ladies are looking for good men and good fathers to bring into their lives.

And if you’d prefer to date a younger woman, know that James is 54, and he’s seeing women as young as 29.

Oh, and don’t think that being a dad makes you less desirable. I dated a girl who used to go to Central Park with her girlfriends to, in her words, “check out the DILFs.”

Some more good news, if you’re open to one day remarrying: Second marriages are 50 percent more likely to succeed than first marriages, according to the Marriage Foundation. Why? You’re older, wiser, and more experienced, so you’re more likely to make the right choice.

Start Dating

My advice: Don’t wait TOO long to start dating. There is no perfect time. As I learned first-hand, dating is part of the healing process. You can’t move past divorce until you’re moving forward—and that involves getting out and dating.

Dating after divorce. The term may fill you with dread, but it’s something to get excited about—especially if you have a great guide.

Want to talk with a dating coach to get personalized dating advice? Book a free call with me here.

Are you over 40? Here's an article on dating in your 40's as a man or even 50's.

Click here to book your free call with dating coach Connell Barrett


Connell Barrett is an acclaimed dating coach for men. Connell resides in New York City but has helped hundreds of men around the world achieve their dating potential through authenticity. He understands how hard dating after a divorce for a man is and can help. Chat with Connell here. For a recommended list of dating books for men click here. To buy Connell's book Dating Sucks But You Don't, click here.

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Connell Barrett Dating coach for men

I'm dating coach Connell Barrett. I help men build confidence and connect with women by being authentic!

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