5 Dating Tips For Newly Single Men After Divorce (2024)

Dating can be hard. Dating after not dating in a decade or more is even harder. And balancing mental health, family responsibilities, and a dating life when you’ve just gotten divorced can seem insurmountable.

Divorced people have so many emotions to process and new dating etiquette to understand, not to mention the life changes they’ve been through since they were last single. For many divorced men, those changes include now having kids. Dating may seem like it’s just not worth it for many men, so they withdraw into themselves, or pour all the bandwidth into work or their kids.

And while I hate to throw around the “50% of marriages fail” stat, which is too neat and clean without picking apart the data, a significant number of folks are in the same divorce boat. This article is meant to help you brush yourself off, hold your head high, and get back out there again!

After a serious relationship, there’s a natural inclination to want to get right back into the fun, gooey center of dating. You may be tempted to latch onto the first person you talk to on a divorced dating site. But that’s not how real relationships thrive. They need to go through four stages: social, connection, comfort and intimacy.

• Social — This is the first introduction. It may be over a dating app, it may be a social function or through your extended friend network. “Oh, hey, nice to meet you, how long have you lived in this city?”
• Connection — When you realize you have some things in common and want to see each other more. “Yeah, little ones can be challenging. But that’s cool that your kids also like soccer. Maybe our kids can have a little soccer playdate after the next practice.”
• Comfort — This is when you are in that so-called honeymoon phase where you lean on each other and support each other and share more of your thoughts and emotions. You can open up a little more with your baggage. “I didn’t think I’d find someone to Netflix-and-chill with again, and it’s so nice just to binge TV in sweatpants again!”
• Intimacy — The long-term relationship. You’ve been open and honest with each other. You share physical and emotional intimacy. The companionship that you’ve been waiting for again. “I felt broken and like I’d never be put back together again. Thank you for giving me space and just being there for me. Now, where should we go on vacation next year?”

Divorcees tend to want to go right to those last two stages as that’s where they were beforehand and what makes relationships great.  

There are two parts to doing this. The first one is to use your network to help you get out there again. I don’t necessarily mean straight into dating, but, like physically out there. There’s a tendency to want to hibernate and even if you DID want to go out, you don’t even know where to go. Ask your friends to invite you out to places, and say “YES!” Ask them if they know anyone that you might get along with. It can feel embarrassing, but everyone wants to help their friends.

The second aspect is that of emotional regulation. We lose a lot of that when we lose the primary person we speak to. She was the one you came to with wins to celebrate, the one who comforted you after losses and the one who will bounce some ideas off with you for your next story. When that’s all lost, we can feel lost. Men aren’t that great about opening up, and it may have taken us years to be fully honest with our partners. What you need now is to develop or lean on your network for this. If you used to dork out to“Lord of the Rings” with her, join a LoTR film forum. If you guys went hiking together, find fellow hikers who like to discuss trailheads in minutia. 

This one is new and challenging for freshly single folks, especially if the last time you tried to date online you used the shorthand A/S/L for age/sex/location. I have a newly divorced friend who sent me a screenshot of some of his chats on Tinder, and, boy, I just felt so bad for him because at least two of his conversations were bots and he was trying to engage them and be witty. So even though we’re smart guys, we have blinders on when it comes to our emotions.  

A serious dating site like Match can be a welcome partner on the road to recover from divorce and find someone new.

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Attractive women on dating sites receive dozens if not hundreds of unsolicited messages every day. So use your head (the correct one) when chatting online. If she contacts you and is super beautiful and it seems too good to be true, it probably is. Also, look at the syntax and grammer in the messages and see if it sounds like the natural way someone would speak. This is an actual message to my buddy: “How long have you been using this software and what are you looking for here?” I asked him, “When was the last time you heard “software” in casual conversation?”

This has been said before, but I’ll say it too because it is important. Don’t give any money, passwords, specific personal information or anything else online. Verify that the person is who they say they are. You can also run reverse image searches on any photos, to make sure you’re not getting catfished. (I have personally found at least four profiles, using one of my photos, on social media.)

Divorce can be a new beginning, but not if you stick to old patterns. You may go after a woman who is similar to your ex for obvious reasons. Maybe it’s your type, maybe you’re more familiar with West Coast girls as opposed to East Coast girls. Maybe you want to fill that emotional hole with someone who speaks and looks like past comfort. But perhaps that first choice wasn’t the best one, as it didn’t work out.

I encourage folks to try new things and possibilities because not only are you adding to yourself, but you never know what can happen when you open yourself a little wider. I have a client — a very rich divorced woman  — who is working on rebuilding her confidence. That’s an important first step for dating after divorce.

This newly single woman has only dealt with people in certain social circles, and while she understands them, they’re all similar people with the same opinions and attitudes. So I have been taking her out to really diverse places to meet new and interesting people who she would not otherwise encounter, and while initially tentative, she’s now having the time of her life!

I hear many times, “I don’t want to date, what would it look like to the kids?” Or, “I just want to focus on the kids until they’re out of the house.” But what I actually hear from the adult children of divorced parents is that watching their father date helped them learn how to date, how to treat people, how to deal with rejection, and other important interpersonal skills. You learn to see your parent as a person and it can be an incredibly bonding experience.

Instead of slogging it out alone, show your kids how you are picking yourself up, brushing yourself off, holding your head up high and becoming the type of person you hope they can be. Obviously, don’t rush into things with kids, but you don’t have to hide it from them. They love you, they want you to be happy!

Divorce can feel like a mini-death. A death of a relationship, the death of a possible future, the death of “us.” But there is life after divorce.

It’s okay to take time and grieve and feel your emotions. And you don’t need to hold it all in. Anyone going through a divorce, or who has had a breakup experience, is going to understand that it’s a process.

Take it slow, let yourself breathe, learn from your mistakes, and, hopefully, you’ll find that next great companion who actually knows who Squirtle is!