5 tips for dating after divorce and what I wish I knew

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The idea of dating after a divorce can be paralyzing for so many people — men and women alike. 

I've been in a serious, long-term, live-in, own-two-homes-together relationship with a wonderful man for 5 years, but I dated like CRAZY for 5-6 years before that. Lots of casual sex, a few boyfriends, and plenty of in-between — including a year-long affair with a Danish man who took me sailing in the Nordic sea one summer.

Long-story-short: I had a very good time dating, and I want that for you, too.

My tips for dating after divorce:

Here are my tips for dating after divorce:

1. Have fun

I understand why you are looking for a new husband — you likely were used to being married, you feel left out because everyone around you seems to be happily married (trust me, they're not). The idea of dating casually may be new, or foreign, or just scary. After all, the very real threat of a post-divorce rebound breakup looms large. I get it.

That said, try to lighten up. Have fun. Go out with people you don't really want to be serious with — older guys, younger guys, guys outside of your demo, women, dads with kids, people without kids. Try online dating (Read our roundup of best online dating apps for single parents).

Try hookup apps, and try friends with benefits. Have fun. Though the heartbreak will come no matter what, but try to have fun until then.

2. Don't rush into a serious relationship!

Don't focus on finding a husband — or even a boyfriend. That is a fine goal, but why the rush? There are so many other romantic arrangements to explore. Be as open as free as you are able. Allow yourself to be surprised by what you have not yet experienced — and may enjoy.

Divorce rates for remarriage are very high. Just saying.

3. Take your time

There is no rush to getting into a relationship, to starting to date again, or any other landmarks. Give yourself a year to be a hot, post-divorce mess.

Listen to those red flags!

 “At this stage of my life I know who I am and what I want.” … I hear that often from single moms. Reality?

Divorce rates for second marriages are very high, heartbreak common, and we may not be as wise as we want to believe. When your girlfriends warn you to run, run.

 4. Be positive about dating, men and relationships

Be proud of being a mom! Please do not lie about having kids, be open to dating single dads, and understand that living in your truth, including your parenthood, is sexy and real and will attract all good things to you.

No one wants a girlfriend who hates men, is cynical about relationships or otherwise is a drag about the very gender she is spending time with! I get that you are wounded and lonely and this mess is confusing. Spend time with positive people, even if it means making new friends. Fill your life with joyful activities and otherwise lean into being a single mom.

5. Divorce counseling: Why you should consider post-divorce therapy

Post-divorce counseling can be an excellent way to help you understand the patterns of your marriage, your dating patterns now, understand and process the grief of your breakup, and help you envision and seek out a healthy, happy new relationship. But first, you have to lean into being single.

LeNaya Smith Crawford, a licensed marriage and family therapist in Atlanta, said that therapy is critical to help you find a healthy new relationship.

“Understanding what went wrong in your marriage, the role you played, and making peace with your ex are all part of the inner work needed to find a healthy relationship,” Crawfor says. “Dating from a place of hurt and negatively will affect your new relationship and can cause history to repeat itself. Don’t skip the counseling — it will help your next relationship be happier and healthier!”

“Remember that your kids want you to be happy too (even if on the surface they are crying for you to stay home). You need a life and a partner; having that will make you be a better mom, not a worse one,” said Raffi Bilek, LCSW-C, a relationship counselor at the Baltimore Therapy Center in Baltimore, Md.

I’m not the first person who has suggested to you therapy at this stage of life. Therapy is not a silver bullet of personal growth and healing for everyone, but studies find that quality counseling will help you recognize unhealthy patterns, grieve a loss, and move through trauma.

It can be very helpful to work through your grief and insecurities before dipping your toe into dating too soon, which can only deepen old wounds.

Have more concerns? Here are some answers to common questions about dating after divorce. Even more tips here:

Life after divorce: 12 tips for moving forward and starting in 2022

What I wish I knew about dating after divorce:

1. First thing I wish I knew about dating after divorce

That first big relationship after divorce is BIG, and DEEP and very sexually intense

2. Second thing 

The second lesson I learned about dating after divorce is that first relationship HURTS LIKE HELL when it ends. 

3. Third thing

Final big dating-after-divorce lesson: Dating is new and fresh and fun and exciting at this phase of life. You invent the rules! Try anything you like! 

Your first relationship after divorce

Here’s what I wish I knew about first relationships after divorce:

Does the first relationship after divorce last?

It seems to be a universal experience: When that first relationship after divorce ends it just kills. When that relationship ended, it hurt like a motherfucker! Holy shit did that hurt. Ouchie!! Owwie ow ow ow! Mommy! Make it stop! Please, ow ow owie ouchie ow I can’t take any more!!!

It took me a long time, and a lot of interaction with other, divorced people to figure out why post-divorce rebounds are akin to your body dripping with infected hangnails while, at the same time, a rusty scythe strikes your guts. Again. And again. And again.

Even more than an ending love, all that pain and torment is really about contending with unresolved heartbreak from divorce. You are likely as I was: needing to go through that rebound and the subsequent pain. It served as a critical point of reference through which I dealt with the dissolution of my marriage.

Divorce often robs us of the opportunity to mourn the romantic relationship itself because there is so much practical and logistical hell to contend with at the time of the split. Including:

Is the first relationship after divorce doomed?

No! Not all first relationships after divorce end. But most do. That’s OK!

5 tips for dating after divorce

First relationship and sex after divorce

After my post-divorce rebound, I needed another rebound relationship. I happened to be his first post-divorce rebound relationship. I couldn’t believe my good fortune, especially after fear that I would never find love after divorce.

My first serious relationship after divorce

Me: “I’ve been thinking about how the first time you sleep with someone, you’re not really sleeping with that person — you’re really sleeping with all the other people you’ve had sex with before them.”

Him: “That’s right. You’re really sleeping with your point of reference.”

In essence, before you get to know a new lover’s body and preferences — as well as how your own body and preferences fit with that person — each of us is really just sorting through all of the bodies and preferences that came before in order to truly enjoy current company.

Relationships are no different. And this analogy holds most true in a rebound relationship.

There has been plenty written on the perils of the rebound. The old maxim suggests that the recently heart-broken is too angry/vulnerable/hurt to be truly open to a new love. The rebounder is at risk of attaching too quickly to the wrong person, and those dating a rebounder are subject to wandering into the line of fire of scatter-shot devotion.

I’ve written exhaustively about my own post-marriage rebound with a man who was also recently divorced. It lasted a full year and was thrilling, wonderful and dysfunctional.

When that relationship ended, it hurt like a motherfucker! Holy shit did that hurt. Ochie!! Owwie ow ow ow! Mommy! Make it stop! Please, ow ow owie ouchie ow I can’t take any more!!! Even more than an ending love, all that pain and torment was really about contending with unresolved heartbreak from my divorce. But I needed to go through that rebound and the subsequent pain. It served as a critical point of reference through which I dealt with the dissolution of my marriage.

Dating a widower: 6 things you need to know

Falling in love too soon after divorce

But no matter how much I tried to stay true to my belief that anything is possible in love, there was no escaping that I am three years out of my marriage while he is a mere three weeks. This guy’s giddy openness about starting life anew reminded me of just how I felt at that juncture.

I also sensed a vulnerability and neediness that was woefully familiar — in this man I could see myself two years ago when I, too, first ventured into post-divorce dating. It evoked being on a third date with my own rebound boyfriend. Anxiously, across the table in a dimly lit West Village restaurant, I stammered: “Are you dating anyone else? Because I’m not.” My barely salvaged heart could barely stand the risk of being dinged yet again.

Today, I feel differently about emotional risk, heartbreak and dating. On the one hand, bring it on! You don’t get to the good stuff in relationships without putting yourself out there emotionally. But now I don’t feel quite as vulnerable and needy. I am feeling strong and free and optimistic about love in a different, more grounded way — one that allows me to see obvious love landmines before I enthusiastically dance on one. As such, I couldn’t figure out how to make my own phase of divorce jibe with that of my recent amour.

So in a breakup email exchange, I shared more or less what I said here. I added that I hoped we could stay connected in some way, keep open the possibility of finding each other in other phases of our journeys. What I got in response was one of the most touching compliments I’ve received in a very long time. It said:

“I can’t think of anyone I would rather have lost my divorce virginity to.”

What to know about dating while going through a divorce

Can you find true love after divorce?

Answer: Yes.

One data point: Me.

I separated from my husband when I was 33 and pregnant with a toddler. A year and a half later I started to date. I dated like a maniac and had a blast meeting all kinds of wonderful, mediocre and weird men. Tons of sex, fell in love once or twice, made some new friends and a bunch of stories. Three years ago I feel in love with a wonderful man who loves me, loves my kids, and wants to spend his life with me.

I’m not special. I’m a little fat, pretty loud, frequently grumpy and fickle.

Here is my list of the best dating sites and apps for single moms

For finding a serious relationship, a boyfriend or a husband, eharmony is the leader:

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Learn more about eharmony in my review.

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Should you get back together with an ex after a breakup?

Lots of people do, with a lot of success. Here are reasons not to get back together with an ex after breakup:

  • You want totally different things and you believe you will change him.
  • You want totally different things and you are ready to make major, soul-crushing compromises to make it work.
  • Abuse.
  • You know in your heart is wrong but you’re so lonely. Or horny.
  • You tell yourself you’ll just hook up with no feelings involved.
  • You’re miserable with him, if comfortable.

How long should you wait to date after divorce?

The general rule of thumb for doing anything major after divorce is: Wait a year. But nothing magical happens after a year. Also: Dating is not major, unless you make it major.

It is fine if you want to date casually, get laid, have fun. But for the love of god don’t do any committing — no moving in with a man, no getting pregnant or buying real estate together!

Read this post: After divorce you get a year to be a hot mess

Also, the answer to this question depends on where you live. For example, in many places where you can easily get divorced within 30 days, it is taboo to date while legally married. However, in New York where I live, everyone dates while they are separated, but legally married, because it takes FOREVER to get the paperwork finalized.

[56 questions to ask before marriage]

Is it hard to meet someone after divorce?

This is a common question, which really cloaks your fear that you are unlovable. Millions of people date, fall in love, fall in lust, get into relationships and even marry after breakups and divorce. Many of them have kids, all of them are wounded, human and lovable. Many divorced people prefer to date other divorced people — you get each other!

All about red flags to watch out for while dating

How do I start dating after divorce at 30, 40, or 50?

Once I the divorce fog lifted, the post-divorce breakup wound healed, I started dating like crazy. I probably went on more than 100 or 200 first-dates in five years, before I met my wonder now-boyfriend.

Warning: You will receive all kinds of toxic messages about your chances of meeting someone after divorce — and the older you are, the more negatively is likely to come your way.

Messages like:

There are no good guys out there at this stage — you're 30! [actual quote directed at me by a loved one]

All the great men in their 40s are already taken.

No one wants a divorced, single mom in her 50s. Used goods!

Men in their 40s/50s/60s only want to date women without kids in their 20s/30s/40s.

If you believe these messages they will become a self-fulfilling prophecy. You manifest what you think.

Fact: There are just as many divorced, heartbroken, single dads as there are single moms. Men are humans, and they also want deep connection, or fun, or commitment, depending on the phase of their journey — just like you!

Here is my advice, which is also informed by thousands of moms who have shared their experiences with the joys and horrors of dating at this phase of life:

  1. First, set some guidelines for yourself and understand that an immediate spark over mojitos after work does not mean you should make a serious commitment to anyone, anytime soon! Dating is not about finding a husband. It is about meeting new people, exploring romantic possibilities and learning about yourself. Hopefully, it also includes some fun and good sex.
  2. If you’re looking for men to meet, ask friends to set you up, consider online dating or go ahead and ask out that guy at the coffee shop you’ve been crushing on.
  3. Pay attention to how you feel. This is a process, and you will be working through a lot of feelings and baggage. Are you really angry at all the men you meet? Feel so vulnerable every time someone pays you attention? Terrified of being left (again)? All normal!
  4. Pay attention to how men react to you. Do any themes emerge? Do they tend to find you clingy, or angry at men overall? Are you stand-offish, or prickly? Don’t dismiss the entire gender, but instead use this as an opportunity to discover things about yourself that will help you heal and attract the type of relationship you are looking for.
  5. Be open to different types of men. Again, this is not a marriage hunt, but dating! Date against type, both in terms of profession and physical characteristics you tend to attract. Heck, date against political party!
  6. Be open to new sexual experiences.
  7. Safe sex, ladies.
  8. Don’t expect immediate chemistry — or for a lightning bolt to hit you when you meet the one. We’re not in a Disney movie, after all. And how many divorces started with “I knew he was the one!”?

23 sexy date night ideas

Why is dating after divorce so hard?

First, you are traumatized by your divorce, no matter how wanted or amicable it was. Divorce is a big fucking deal, and it can take a long time to get over. Totally normal.

Second, you are afraid of getting hurt. You are licking your wounds from your breakup, and are very timid about making yourself vulnerable to that again. 100% healthy.

Third, you likely have not dated for a long time — decades even. You worry you are unattractive, unsexy, fat and out-of-touch with the dating world. Online dating? WHAT?! Getting naked with a man at this stage of life? HUH!? There are so many toxic messages about dating after divorce, or dating later in life, it is no wonder you are hesitant.

In reality, you are just out of practice.

Fourth, you don’t trust yourself. Your picker was off when you committed to your husband, you likely stayed through some horrible behavior, maybe cheating, and you don’t trust your own instincts — especially when it comes to men.

Advice from a 90-year-old single mom on dating after divorce

Last week, my kids and I visited my mom at her Milwaukee condo, the complex of which is occupied mostly by senior citizens. While lounging by the pool where my kids caused a ruckus, mildly amused and mostly annoyed by the very loud woman who went on and on and ON about how she could not believe the restaurant charged her $2.75 to swap the picadillo peppers for onions, I was delighted when a very elegant, spry older woman sat down next to me, put on her wire-rimmed bifocals and dug into her Danielle Steel paperback.

“I’d like to jump in there, too, but I’m going to be 90 this month and probably shouldn’t get into a swimsuit,” was her opening line. That, of course, was cue for me to tell her a) she looks fabulous for her age (true), b) who cares what you look like (truer still), c) engage with her. I’m so glad I did. There were some gems of advice from my new, brilliant friend, and I must share them with you.

First, a quick bio: This beautiful woman grew up in a small, rural midwestern town and became a PhD psychologist. She married her college sweetheart very young. At age 26 after recently giving birth to her only child, a son, her husband unceremoniously “sued me for divorce.”

“He was a heavy smoker, and two years later he was dead,” she said with a shrug. “My parents said, ‘Honey, what do you want to do?’ I said, ‘I want to play the field,’ so they suggested I see the family doctor.’” She had her tubes tied. “I never regretted it for a second,” she told me.

For the past 37 years she has been married to “the love of my life” — a building contractor who just celebrated his 100th birthday. Here are some genius single-mom nuggets from this hot momma:

Always have your own money. 

When her love rang in his centennial birthday, his grubby daughter sent real estate brokers over to the condo to assess its value, intending to sell it. Joke was on her! “When we married, I had money saved from my practice and bought the place I wanted in cash. The house in my maiden name. Always make sure you take care of yourself.”

11 steps to survive financially as a single mom

Marry for love. 

“Mr. Goldstein is the love of my life,” she says. Before him, she dated a prominent lawyer for 12 years until he passed away. “But no one loved me like Mr. Goldstein.”

Do you give an engagement ring for a second marriage?

Marry your financial and professional peer. 

“But Mr. Goldstein was doing very well for himself. Honey, you need someone who respects your career, and you respect his. Don’t settle! And make sure you have your own money, in your own name.”

Enjoy your body. 

“Honey, you’re still young. You look great. Play the field.”

9 reasons sex and dating are better as a single mom

But be careful. 

“That’s great you’re dating. But honey, be sure to protect yourself. Don’t get pregnant.”

P.S. Enjoy your body. 

“When I went for my annual exam, the doctor said, ‘You look like a young girl on the inside! You could still be having active sex!’

When I asked her if she and her husband still had sex she said: “Oh no. Not any more.” Did she miss it? “Sometimes. Honey, play the field.”

How to be confident when you feel old, gross and fat

Don’t stop playing the field. 

“The other day I was in Pick ‘N’ Save and I ran into a doctor I knew 40 years ago. He told his daughter, ‘I knew her years ago, and when her husband dies I’m going to marry her!’”

Bottom line: Dating after divorce does not have to be difficult

Have fun, embrace your new freedom, set positive example for dating for your kids and enjoy your body.

Does the first relationship after divorce last?

It seems to be a universal experience: When that first relationship after divorce ends it just kills.


Is the first relationship after divorce doomed?

No! Not all first relationships after divorce end. But most do. That’s OK!


Can you find true love after divorce?

Answer: Yes.

Should you get back together with an ex after a breakup?

Lots of people do, with a lot of success. But there are lots of reasons not to.

How long should you wait to date after divorce?

The general rule of thumb for doing anything major after divorce is: Wait a year. But nothing magical happens after a year. Also: Dating is not major, unless you make it major.

Is it hard to meet someone after divorce?

This is a common question, which really cloaks your fear that you are unlovable. Millions of people date, fall in love, fall in lust, get into relationships and even marry after breakups and divorce. Many of them have kids, all of them are wounded, human and lovable. Many divorced people prefer to date other divorced people — you get each other!

Why is dating after divorce so hard?

In reality, you are just out of practice.

Wealthysinglemommy.com founder Emma Johnson is an award-winning business journalist, activist, author and expert. A former Associated Press reporter and MSN Money columnist, Emma has appeared on CNBC, New York Times, Wall Street Journal, NPR, TIME, The Doctors, Elle, O, The Oprah Magazine. Winner of Parents magazine’s “Best of the Web” and a New York Observer “Most Eligible New Yorker," her #1 bestseller, The Kickass Single Mom (Penguin), was a New York Post Must Read. As an expert on divorce and gender, Emma presented at the United Nations Summit for Gender Equality and multiple state legislature hearings. More about Emma's credentials.

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