The Top 10 Dating Mistakes Men Make After Divorce

Post Divorce Dating Mistakes

Dating after divorce is hard.  I know because I’m living it.

After being married for 8-10 years, I can still remember the anxiety that I felt as I prepared to re-enter the dating world.  I was navigating unfamiliar territory.  I now wish I had a cheat sheet to help me avoid the inevitable blunders I was to make along the way.

My loss is your gain as I’ve analyzed the top dating mistakes that men make after divorce.

But this isn’t just a list.  In addition to giving insight into the cause of these mistakes, I’ll provide some practical tips for avoiding these situations and recovering should you have already committed an offense.

Dating norms have changed since you were single.  Instead of wasting your time fumbling around the dating world, come with me as I teach you how to easily spot and avoid these mistakes.  Your love life depends on it.

1.  Speaking poorly about your ex

This is without a doubt one of the most common dating mistakes divorced men make (and women are just as guilty, I’ve learned).  If your divorce is fresh then it’s easy to get carried away with war stories, and even bond over them if you’re also dating a divorcee.

But if you really think about it, what message are you sending?  It makes you look like a bitter guy who is jaded by divorce or, much worse, isn’t over his ex.

Most women are notoriously suspicious of newly divorced men for the reasons just mentioned.  Don’t blow your chance by bad-mouthing your ex or wallowing in self-pity.  Your date will not be impressed.

The Fix: Focus on the woman in front of you

Before I go into every first first date, I mentally review my ground rules for discussing my ex wife.  Ideally, a detailed discussion about exes will not come up on a first date, but just in case I like to be prepared.

Talking points that could earn you brownie points

  • That you are still on good terms (she’s still alive, right?)
  • That you wish the best for her [for the sake of the kids]
  • That you still support each other

Discussion topic that could be your undoing

  • Criticizing or demeaning your ex in any way
  • Asking your date any probing questions about their  own ex or divorce

By taking a mental note of these ground rules, I prepare myself so that if the subject comes up, I’ll have a few simple talking points to keep me on track.

Once these bases are covered, I steer the discussion in a different and more pleasant direction.  There will be plenty of time to dig deeper into this subject if you hit it off.

The Recovery: Turn negatives into a  positive

If you slip-up and catch yourself committing a faux pas regarding your ex, try to turn the narrative into a positive.  Emphasize that the hardship was a learning experience, that you’re a better man because of it, and you are excited about what the future has in store.

2.  Limiting your dating pool to your social circle

Online dating outside social circle

How many women did you socialize with while you were married?

If you are like me, 99% of the women I associated with while married were either personal friends, work colleagues, or my ex-wife’s friends.  And unfortunately, women in these categories aren’t optimal candidates for romance.

Dating co-workers is a bad idea for several reasons.  Friends are likely just that- friends.  And dating one of your ex-wife friends is just asking for trouble, for obvious reasons.

Not only is dating within your social circle is asking for drama, it’s extraordinarily limiting!  Thanks to the Al Gore and the Internet, there is a much better way.

The Fix:  Online dating to the rescue

Through online dating I have been able to increase my dating pool exponentially by joining sites like and eHarmony.  These are mainstream sites with no shortage of attractive, available women who are looking for guys just like us.

The benefits of online dating are too many to mention, so check out my review and eHarmoney review to determine which site would work best for you and your target demographic. Both reviews are written with divorced men in mind.

The Recovery:  Increase your exposure organically

If you tried online dating and it just wasn’t for you, your next best option is to increase your potential dating pool organically.  That means getting out of  your house, getting involved in the community, and meeting new people.

For example, you could joining a Meet-Up group.  I recently joined 3 local Meet-Ups in my area, one for singles and two for programmers and entrepreneurs.

Want to get some female exposure and make the world a better place at the same time?  You could get involved in your church, or volunteer at a local place of need (such as a pet sanctuary or homeless shelter).

Remember, your odds of landing a date increase as the number of women you encounter grows (If my memory of high school algebra serve me correctly, I think this means they’re directly proportional).  Yes, I’m a nerd.

If interacting with women in cyberspace isn’t your thing, you’ll need to find another way to get that much needed exposure.  Getting involved in your community is the next best thing.

3.  Putting on an act to impress her


Sure, when I first started dating after being separated for a year I was very insecure.  I was nearing my 40’s and had no actual proof that I still had it after 8 years of marriage and 12+ years of monogamy.  It’s natural to assume that your best years are behind you.

The temptation was there to portray the role of the suave player or the fat-pocketed baller.  After all, I had to do something to make-up for the fact that I was damaged goods with side of baggage. But there was one problem with that approach:

I am neither a player nor a baller.

And although I was routinely given the side-eye from women who found out I was recently divorced, I actually didn’t have much baggage.  So I ultimately made the decision to put myself out there- as myself.

Yes my divorce was a torturous hell-ride, but I came out of it feeling like I could take on the world.  Women would either have to accept me as I am, or I’d just move on to the next one.  With at least 3.5 billion women walking the Earth, I like my chances.

The Fix: Put your best foot forward, but be yourself

If a women doesn’t like you for who you are, then you simply aren’t compatible with that woman.  Do both of you a favor and move on.

Don’t conceal yourself behind a mask that will eventually have to come off.  Put the best version of you out there, and work each day to create a better version of yourself.

The Recovery: Honesty is the best policy

If you insist on projecting a false persona, and a woman catches onto your act, the best you can do is say you’re nervous and haven’t had a chance to build-up your confidence post-divorce.

If you’re lucky, your date might show some compassion and give you one strike.  At that point, drop the act and start charming the hell out of her because you’ve got an up-hill battle.

4.  Initiating sex talk on the first date

Male and female sex symbols

Of all the dating mistakes men make, this one has to be the dumbest.  Luckily, it is also the most preventable if you use your head (the one on your shoulders).

Sure, women love sex as much as men do.  But if your date hasn’t broached the subject, it’s best to delay your BDSM discussion until you’ve had a date or two to feel each other out.

Most women aren’t going jump into a man’s bed on the first date, so volunteering your favorite sexual position isn’t going to serve much of a purpose, except to make your date’s legs slam shut.  Do your best to keep things tame.

The Fix:  Let the woman lead the way

Instead of initiating sex talk on the first date, let the woman lead the way.  If she keeps the conversation basic and non-sexual then you’d be wise to do the same.

Some women are comfortable talking about sex and intimacy almost immediately.  If they do, then they’ve give you the green-light to let your freak flag fly.

The Recovery:  Reign yourself in quickly

If you’ve already alienated your date by turning the conversation to sex, your chances of recovery are slim to none.  Your only option would be to somehow balance-out the filthy conversation with discussions about rainbows and teddy bears.

5.  Making yourself the center of attention

Think about it.  What does a women want?   She wants to know that you’re interested in her.  Blabbing-on endlessly about yourself will only make it appear that you’re too absorbed with yourself to pay attention to your date.

Getting a woman interested in you means being interested in her and what she has to say.  It a two-way street.

The Fix:  Let the woman lead

Women love to talk, especially about themselves.  As a man it’s your job to shut-up, listen, and at the very least appear interested and engaged.

Encourage your date to talk about herself by asking open-ended questions about subjects that interest her.  No one wants to be be asked interview questions on the first date, so skip the “Tell me about yourself” or “What do you like to do for fun”.

If you found your date using online dating, then you should have at least a general idea of her interests, so start there.  If you know absolutely nothing about this person, guage what she’s interested in, then probe deeper.

The Recovery:  Flip the script

If you catch yourself filibustering during the date, simply apologize and turn the attention back to your date.  Women like talking about themselves and things that affect them, so give them a few softball questions and watch ’em go.

“Where do you like to travel?”  “What are you most passionate about?”   “Tell me about your cat.”  Any of these will suffice.

6.  Splitting the dinner bill

Insist on picking up the bill when you date.

I know this is the 21st century and men and women are supposed to be on equal footing.  Girl power, female empowerment, feminism, yada yada yada  But make no mistake about it:

When it comes to dating, expecting a women to split the bill is never a good idea.

Some men believe that going dutch is the new norm.  It isn’t.  Will it ever be the norm?  Probably not.  As much as people today want to blur gender roles, they’re engrained in our DNA.

To illustrate this point, let’s assume for a second you do suggest splitting the bill.  What are the possible outcomes?

  1. She happily agrees to pay her part (because everyone likes spending their own money, right?)
  2. She grudgingly agrees to pay (but gives you a strike)
  3. She is completely offended and the date is a bust

Even if women who like splitting the dinner bill actually existed (they don’t), you’d still lose in two of the above three scenarios.  Do you really want to play those odds to make a point or save a few bucks?

With the advent of online dating, the margin for error is so small that you have to take advantage of every sure-thing.  This means not risking offending your date by asking her to split the bill.  This will be one less strike against you and maybe she’ll let you slide for saying something really stupid after the 4th or 5th drink.

The fix:  Don’t even give her the option to pay

If you want to show your date that you observe gender equality, find another way to prove you’re down for the movement.  Pop-in the latest cd by Pussy Riot on the ride home or let her open the door for you.  Hell, even lie and say you don’t mind that she doesn’t shave her legs.

But whatever you do, insist that you’re picking up the bill.  And do so with a big, wide grin on your face.

After you’ve proven that you have no qualms about dropping cash on your date, most women will instinctively want to treat you- and that’s fine.  But early on, play it safe you cheapskate.

The Recovery:  Next time use your head

I hear so many horror stories from women who were blindsided by men who invited them to dinner then asked them to pay.  These clueless tightwads are even using an app called Venmo to request their dates pony-up for half the tab – days after the date!  You can imagine the backlash.  It’s not a pretty story.

I truly don’t think there is any recovering from this blunder.  You’re on your own on this one.  Tell me in the comments if it has ever worked out well for you.

8.  Getting ‘friend zoned’

Image of a Friend Zone logo.

If you’ve spent any time online dating, you’ll notice that in many women’s profile there is some mention of wanting to “be friends first, then see where things lead”.  My personal theory is that this is a pre-emptive maneuver meant to make it easier  on her to discard unwanted suitors.

This subtle stipulation removes the pressure of hooking up with or even rejecting bad dates because after all, you’re just figuring out if you should be friends or not.  But make no mistake, if a woman is attracted you and senses chemistry then the friendship requirement will be promptly waived.

Women aren’t on dating sites to make friends

Yes, it is true that romantic relationships sometimes evolve from friendships.  But if you’re actively going on dates then the assumption is that there is some level of initial, mutual attraction and romance is at the very least an option.

While you should obviously respect boundaries, at some point you’ll need to initiate physical contact to show your interest.  If you make it through the second date continuing to act more like a chum than a romantic interest, you risk being banished to the darkest, most horrifying realm of the dating world – the Friend Zone.

The fix: Read the signals and initiate physical contact

If your date doesn’t make the first move (in most cases the woman won’t), then it’s up to you to know when the time is right.  While it’s important to be a gentlemen, the last thing you want is your date to conclude that you aren’t interested or that there isn’t a spark between you two.

You’ll never know if she’s attracted to you if you don’t make a move.  Try holding her hand and read her body language.  If she repeated flicks her hair or interlocks her fingers with yours when you hold hands, you’re on the right track.

The Recovery:  Make your intentions clear

The unimaginable power of the Friend Zone is such that almost no one can escape.  If you play your cards poorly and find yourself is this graveyard of lost souls, your only chance for escape is to make your romantic intentions crystal clear and hope that your date hasn’t already mentally moved on.  

However, the laws of the dating universe are not on your side.

8.  Not giving your date your undivided attention

Sure you’ve got a cool phone, but texting away while your date talks about her day is a sure-fire way to turn her vagina into the Sahara.  So is checking out Facebook, sending tweets, or even answering your phone.

In addition to cutting the digital cord, try keeping your eyes in your head.  Sure, the waitress may have the best ass you’ve see in ages, but for tonight at least you have little chance of going home with her.  Focus on the task at-hand: the woman sitting across from you.

The Fix:  Leave the Phone in the Car

I don’t care who you are, you’re not so important that you can’t cut-off outside distractions for an hour or two to focus on your date.  Be a big boy, leave your phone in the car, and if you must check your messages then do so while she freshens-up in the bathroom.

What if a situation arises where you absolutely need to use your phone?  Maybe you want to look up the business hours of an after-dinner bar for phase 2 of your date?  Then I guess you’ll just have to earn some brownie points from your date by admitting:

you left your phone in your car because you wanted to focus on her.

The Recovery:  Keep it brief and apologize

If you simply can’t cut the cord, then limit your talk time to emergencies and politely excuse yourself from the table to take the call.  Make it brief, return to the table, and apologize.

If you get busted glaring at another woman, insist that she looks like your sister or say you worked with her at the local soup kitchen.  I don’t have all the answers.

9.  Planning an expensive first date

Arranging an expensive first date is common (and costly) mistake that many guys make when they re-enter the dating pool after a divorce.  These guys have the best of intentions and will likely have more long-term dating success than the cheapos.  But they could burn through an exorbitant amount of cash in the process.

Modern dating (and especially Internet dating) is so casual and unpredictable that first dates almost never involve dinner– much less an expensive dinner.  Current social norms dictate that a first date should be casual and in a zero-pressure environment.

If you were married for a significant amount of time, I know this probably goes against everything you ever knew about dating.  But take my word for it:

Dinners on a first date are no longer the norm.  

First dates are now largely quick meet-and-greets where you determine if the other person is worth going on a real date with.  If either of you don’t catch a good vibe or there is no chemistry, you can simply walk after a drink or two.

The Fix: Arrange a thoughtful, but practical first date

Instead of a fancy dinner, plan something simple for the first time together.  I almost always suggest a first meeting over drinks at a low-key, local bar.  Not once has a potential date ever been offended by this suggestion.

There is always the option of progressing to a level-two destination if the date is going well, but if not the investment was minimal and I live to date another day.

If boozing isn’t your thing, you could opt for other casual, but escapable venues.  A walk through the park, a waltz through an art gallery, or maybe a cup of coffee might work better for you.

The type of woman who might be the exception this rule

I’ve admittedly scheduled dinner dates when I felt that it was the right call for the situation.  For instance, going out with a newly-divorced woman who I recognized had a very traditional attitude toward dating.  In this type of case, there is nothing wrong with splurging; just apply common sense and you’ll be fine.

The Recovery:  Grit your teeth and bear it

The worst possible outcome of an ill-advised, first dinner date is that you immediately realize there is no attraction.  Maybe the women doesn’t look like her pictures.  Maybe she has a lazy-eye. Regardless of the reason, you now get to sit through (and likely pay for) an entire dinner with someone when you know there likely won’t be a second date.

Instead of being rude, the best course of action in this scenario is to simply ride it out.  It’s possible that she feels the same way about you, so be pleasant and try to make the most of the situation.

You might make a new friend and after all, female friends know other single females.  Turn your dinner-date into a networking event and play it classy.          

10.  Sabotaging potential relationships to ‘trade up’

When men first start dating after divorce, they typically want to date casually and play the field.  Actually, this is a big reason why many women refuse to date men who are recently divorced.  It’s a very real (and unfortunate) phenomenon.

When a divorce is fresh in a man’s mind, we’re still pretty shell-shocked.  Because of this, the decision to get serious with a new woman could easily lead to a rebound relationship.

Playing the field isn’t necessarily a bad thing, but at some point most men will begin seeking a healthy, monogamous relationship.  But as men we know:

Casual dating habits are especially hard to break.

I speak from experience here.  I’ve dated some great, beautiful women with whom I could conceivably see myself in a monogamous relationship.  But I sometimes caught myself looking for that upgrade, be it out on the town or while feverishly swiping through profiles on Tinder.

It is true, the odds are great that there is another women out there who is either hotter or more fun than your current girlfriend.  However, unless you’re George Clooney or Brad Pitt, there is an upper-limit to the number of women that are mutually interested in you.

The Fix:  Honestly define your relationship goals and date accordingly

If you value variety over quality, then by all means continue to play the field and reap the rewards.  That is a perfectly legitimate dating strategy and this mistake doesn’t apply to you.

But if you’re seeking a woman to be a long-term partner, then repeatedly neglecting promising relationships while you search for a better one is not a sustainable strategy.  At some point your attempt at an upgrade will fail and you’ll find yourself completely alone.

Exclusivity doesn’t equal marriage.  If a woman makes you happy, and you desire monogamy, why not give her a shot a the prize?  Uninstall those dating apps, consider yourself a post-divorce dating success story, and bask in your monogamous glory.

The Recovery:  Soul searching v2.0 is in order

So you pushed your luck, blew your potential relationship in search of an upgrade, and it turned out the grass wasn’t greener on the other side.  Now what?

If you bailed on one potentially successful relationship to pursue something better, it might be time to accept that right now monogamy simply isn’t in the cards.  You still love the thrill of the hunt and it’s probably best to avoid relationships altogether until you’ve had your fill of strange.

When you do decide give relationships another try, just be the wiser and learn from your past discretions.  There is an optimal dating strategy for everyone.


For divorced men, the post-divorce dating scene is rife confusion and pitfalls.  We’re rusty, extremely horny, and can sometimes be completely lost in this new landscape of online dating.

But I truly believe that if you can learn to avoid the dating mistakes outlined in this article, you will be successful at dating after divorce.

Dating blunders are bound to happen, especially if you’ve been out of the scene for awhile.  But by avoiding the most common dating mistakes that divorced men make, you’ll avoid  embarrassing situations and increase your chances of early-stage success.

With a little practice, you’ll be back into the dating groove and capitalizing on your newfound freedom.

About the Author Brad Pinch

Brad is a divorced father of two who is navigating the brave new world of dating after divorce. A software developer by trade, he experiments with the latest dating applications and tools so that you don’t have to. Brad writes online dating reviews along with other actionable content for men to improve their quality of life after divorce.

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