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The Divorced Dude’s Guide to Dating

That profile isn’t gonna cut it anymore, pal

Coming out of a marriage and into the brave new world of singledom, especially if you were married before the advent of dating apps, can feel like you’re a domesticated seal that’s suddenly been released into the wild. You’re defenseless in the face of scams, bots and swiping sharks, lost in an ocean of shallow interactions and meaningless matches.

I’d like to help, though.

For starters, I have a lot of personal experience in this realm, having been divorced myself as well as having assisted more than a few divorcées in their transition from married to single. It’s enough of a personal interest, in fact, that I recently posed the following question via Twitter: What are the most important things you wished you knew about dating coming out of divorce?

Men of all ages and marriage lengths responded. Some were married too young and are now single again in their 30s. Some had been cheated on by their wives and felt broken and jaded. Some had been married since the 1990s, and things fell apart when the kids left for college. Universally, though, they had a ton to say about a range of topics — from the current political climate to dealing with exes to the shock of online dating to casual sex versus companionship to what it took to get their swagger back.

It was all smart, useful and heartbreaking enough to pay it forward. So while I hope you never find yourself in the same situation, if you do, here’s their (and my) handy guide on how to navigate the modern avenues toward love and commitment…

Phase I: All By Your Lonesome

Maybe you were married one year; maybe you were married 15 years. It doesn’t matter, what matters now is: You’re alone, and you’re freaking out a little. Before you give into the temptation of the male ego that tells you to bang as many women as possible to get back at your ex-wife, hear me out…

Do Not Immediately Get Into Another Relationship. I cannot emphasize this enough, and yet, it happens all the time. You’re kind of like a prisoner who plans their escape, but who has no plan for when they end up back in prison. Matt warns, “The first person I dated after divorce, I had tremendous feelings for and that relationship ended, too, so I think the combo shut off that part of my brain/heart.”

Of course, there are exceptions to every rule — you might meet the love of your life two days after your divorce is settled. But nine times out of ten, these rebounds are a shit show and end up causing more pain in the long run.

Wait to Date. Just because you’re a dude, doesn’t mean you don’t need time to heal and grieve. Divorce is traumatic, no matter how long you were married and even more so if kids are involved. Kevin says, “I went on a couple dates shortly after I was separated, and I wish someone had told me at the time I wasn’t ready.” Almost all the men I spoke to said it took about a year before they were truly ready to date, even if they were already out and dating right away. Josh explains, “Things are still too fresh under a year, IMHO, and you’re doing yourself and those you date a disservice.”

In other words: Don’t give into the peer pressure to “get back out there” if you haven’t fully accepted your new relationship status. Ultimately, it can leave you feeling even emptier and more depressed. As Justin says, “I definitely should have waited to date, because for over a year, I wasn’t over my divorce and hadn’t realized I’d speak about my ex-wife all through the dates without even knowing it.”

Get Comfortable Being Alone. Your first job as a newly single man is getting comfortable with being uncomfortable. “After the divorce, I felt like I had to hurry to get back into something long-term and stable. That’s where I was comfortable,” Tim explains. “I wish I’d known that uncertainty/loneliness isn’t so bad, and is probably healthy.”

Boost Your Confidence. “Divorce is a giant awful rejection,” says Travis. Even if you were the one to leave, but especially, if your ex-wife left and/or cheated on you. You rebuild self-esteem, however, by doing esteemable things. Go to the gym. Get yourself some new clothes. Focus on your kids. Step it up at work. “I didn’t even know if I was still attractive to women,” Aaron explains.

Maybe go on some dates but keep it casual. “Don’t think too much,” Josh adds. “I took myself and the process too seriously. The next one is probably not the ONE. Just have fun and be open.”

A word of warning, though: If you have that friend you’ve always been attracted to, but could never date, don’t date her right out of your marriage unless you’re willing to lose the friendship — because you probably will.

Phase II: Modern Dating

Okay, so you’re seeing a therapist, you got a new jacket and you feel ready to dip your toe in the dating pool. Here is a quick cheat sheet of things to know as you enter the thunderdome.

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Dating as a Practice. The first thing you need to know is: Dating fucking sucks. It’s time-consuming and can be defeating. But look at every date as a chance to hone your skills because you’re probably rusty after years of domestication. Once you accept that, it gets easier. “Every person you meet is an opportunity to practice flirting,” Larry says. “Not in creepy way, but to work those skills, being aware of body language and cues, so they become second nature and the instinct kicks in when needed.”

Politics Matter Now. Like, a lot. In fact, according to my therapist, politics might very well be the thing that caused your divorce. It’s sad that we’ve descended into toxic tribalism, but here we are. No matter how attracted you are to her, if you can’t stand hearing about the #resistance (or #MAGA) every day, it’s never going to work because you’re going to hear about it. Every day.

Sexual Relations. If you’ve only had sex with one woman in the past decade, it isn’t weird to feel nervous about your sex skills. Not to mention, per Larry: “Chemistry is random! I used to beat myself up over why there was no chemistry, but there are so many variables at play, I realized there is no one reason.”

“I married my high school sweetheart, and between dating and marriage, I wasn’t in the singles’ pool from 1998 until 2011,” Eric adds. “I was — and in many ways still am — a puppy thrown to wolves.”

But have no fear: It’s like riding a bike. You might be shaky at first, but you’ll get the hang of it. Plus, women are more than happy to help liberate you. “Women in their late 30s and 40s are certainly way more DTF than I was aware of getting married at 27 and divorced at 45,” says Michael. “I thought it was just guys, but wow, that was an eye opener — and for the good.”

That being said: WRAP IT UP.

To Pay or Not to Pay. Despite where we’re at with gender equality, most women still don’t like paying for stuff. They’ll act all outraged that I just said that and do a fake reach for their purse on your date, but I promise you, they have $6 in their wallet, and they’ll talk about how cheap you are to their friends if you don’t pick up the tab.

The general rule is if you asked her on a date, expect to pay. Other than that, though, chivalry is dead. “I wished I knew that being a gentleman isn’t looked at well,” says Matt. “Opening doors, offering to drive on date, etc. seems to be frowned upon. I don’t get that.”

I don’t get that either. But here’s the truth: There are many women, like myself, who still appreciate chivalry. So don’t give up. We’re out there.

Dating Apps. The first thing people will suggest is dating apps. This can be jarring when you’re stumbling out of the early 2000s onto the singles scene. All the men I interviewed expressed surprise at how difficult it is to find a meaningful relationship this way. Jason says, “Both men and women now have this plethora of options, and it makes it difficult for one to make a commitment when someone else is just one swipe away.”

I’ve often joked that if I was a marriage counselor, I’d have couples come in and swipe on my dating apps for 45 minutes and ask them, “Are you sure you’re ready for this? You really can’t work it out? Because this is what you’re looking at.”

In fact, if you’re contemplating divorce, I highly recommend you and your spouse borrow some of your single friends’ phones and have at it.

Dating Apps for Dummies. Lemme start with the obvious: In general, swipe right if you find someone attractive and left to reject them. There are, however, variations on this, and often, a dating app will come up with clever ways to get you to pay money to “super swipe” or see who swiped on you or to go back to someone you passed etc.

Some other not-always-so-obvious (especially for the uninitiated) tips, which FWIW were the things the recently divorced men I spoke with were most befuddled by and had wished they’d know about ahead of time:

  • A part of your soul will die every time you swipe left on someone — don’t worry, you get used to it. Until, that is, you eventually delete all your dating apps out of frustration only to download them again out of boredom on a lonely, Friday night. Again, don’t worry, this is perfectly normal dating-app behavior.
  • Tinder isn’t just a hookup app, it’s a dating app people use to hook up. Or simply put, people are also there looking for significant others.
  • Many men asked me, “Why did she swipe right if she didn’t want to see where it went?” Because she’s bored and she wants validation. That’s why.
  • If they’re behind a paywall (like or, they’re the most serious about finding a meaningful relationship because, you know, they’re spending money to do so.
  • All the photos are staged, and it’s her best. Manage your expectations.
  • Under promise and over deliver. I suggest you post photos that are hot but not your hottest, that way, they’re pleasantly surprised instead of disappointed. This also weeds out the shallow ones.
  • If you have kids, don’t hide that fact.
  • No one is as smart and pithy as their bio appears.
  • Carrying on multiple conversations, although amusing, is a waste of time, nail down a time to meet or move on.
  • The first date should be casual, inexpensive, public and easy to leave. Coffee or drinks are ideal.
  • Know what your end game is and communicate it. If she’s looking for a husband and you’re looking for casual sex, don’t waste everyone’s time.
  • People will disappear or “ghost” you. You’ll be having a conversation, and they’ll drop off. You’ll get blocked for no reason. You’ll go on a few dates and never hear from them again. It’s horrific, but it’s part of the process. Don’t get jaded, and if you find that you are, delete your apps for a while and join a bocce league or something. After all, most men said they met more women out doing things they enjoyed than on dating apps.

Phase III: Beyond the First Date

So you haven’t had to flirt with a woman in a decade, but you somehow managed to make it from DM to phone call to coffee to dinner to a great time together. Congratulations! Now what?

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Pick a Way to Communicate. Trying to figure out the best way to converse can get tricky, and to be honest, it varies from person to person. Should you text her or call her? How long should you wait? Too early and you can appear desperate or clingy. Too many days go by, and it appears like you aren’t interested. “Some women are very communicative, but for others, that’s a huge turn-off,” says Ben. “That’s the biggest hurdle for me — how to show them I like them while not overdoing it. Or some woman may think you don’t care if you don’t text/call enough.”

I hate all this shit because I hate games. My advice then: Take the lead. Make your intentions clear but don’t seek approval. Instead, give her space to come to you. Actions speak louder than words, so do what you say you’re going to do. Call when you say you’re going to call. Show up. Don’t flake. Be consistent. If she doesn’t reciprocate, move on to someone who does.

The Ex Factor. There are so many different variables here and so many different types of divorces, it’s nearly impossible to generalize how to handle this portion of your new life. However, there are some pitfalls to be aware of that you might not even have considered:

  1. Don’t underestimate “the invasive effect social media has on the perception of others seeing you with anyone new,” Brent says. This is much harder in small towns so prepare to get “lots of direct questions from family and friends and the ex about your social life after going out.” As best you can, I suggest staying under the radar until you’re ready to come out as a couple.
  2. Don’t expect your family to be cool with your new girlfriend. Divorce affects everyone in the immediate and extended family. As Taylor explains, “Your family might not be as ready for someone new in your life as you are. Everyone accepts the divorce at a different pace. Be patient when integrating someone new.”
  3. Don’t be in competition with your ex to get in a relationship first. If she gets into one before you do, it’s okay. “Let the ex be an EX,” John says. “Otherwise, any new people you start dating will be ‘trophies,’ and you won’t be dating them for THEM.”
  4. “Don’t go out looking for the opposite of your ex-wife,” Craig warns. “There were things you loved about her at one time. Chances are, you still find some of those things attractive in another woman. It’s impossible not to compare someone new to someone you were married to. Even if the new person is winning that comparison in your head, it’s best to keep those comparisons right there — in your head.”
  5. Don’t assume your new lover is over her ex to the extent to which you are over yours. As Jared mentions, “I mostly dated divorcees, most of them weren’t truly ready to move on.”
  6. Do realize how challenging it will be for your girlfriend to have an ex-wife who still tries to cling on or who still loves you or who still relies on you for alimony or child support.

That DILF Life. Many women don’t want anything to do with another woman’s child for fear of baby mama drama. If you have kids, these women aren’t for you, unless it’s causal and you have no intention of them ever meeting your kids. That said, there’s the other side of the coin, too. “I’ve had women ask about when they will see my kids on like the second date,” says Seth. “For me, that was a turn-off and a warning sign.”

How long then should you be dating someone before they meet your kids? Again, there are too many variables to generalize. Brian tells me:

I’ve dated four to five women semi-serious over the past six years and that’s a real tough call, because if the kids get attached explaining a break up to a 4-year-old isn’t fun. That’s why they’ve only met two of the women I’ve dated. The first one broke their hearts, and I was terrified to ever introduce another one to them.

As a child of divorce, I think this is the most important thing you should be asking. It’s confusing enough for kids that their parents are splitting up. Adding a bunch of new characters to the mix is even more unsettling. “I wish I knew that single people were so willing to have people they barely know meet their children,” Donald says. “I’ve picked up dates for the first time and met their child as we greet at the door. To each their own, but no one meets my daughter until there’s something serious.”

My general rule is that if you’re planning on spending the holidays together, it’s probably time to intro the kids.

Scheduling. Scheduling can be tricky as two adult singles. Both of you will more than likely be juggling a career, kids, exes, taking care of aging parents and perhaps going back to school. You’re fully adulting. Add to that the many other variables that make dating and blending families a logistical nightmare. “My last GF couldn’t handle being third — sobriety, kids and then her,” explains Todd. As such, make sure you both fully understand each other’s priorities and where you fit into the equation.

Don’t Settle. Always trust your gut! Don’t tell yourself, “I’ll just give this relationship some more time,” and then, “I need to give it even more time.” You know when something isn’t working.

Or you know, get out before you’re facing divorce #2.