7 Dos and Donts of Online Dating — Post-Divorce

Ok, so you’re 40+ years old, divorced with a kid or two (or possibly more — God bless you!), and you have just awoken to the realization that you’re single, too.

Let’s face it: Dating after divorce is really weird. And I know getting divorced is weird enough without having to add, “Finding another mate to fill up your loneliness,” to your already long to-do list that you’re probably doing alone.

For a while, you went out and did all the things people told you to do: You found a hobby, you took a yoga class, you went on a trip around the world — or you stayed home and wished you had done all of the above. But the truth is, we like companionship. We were built to “co-stuff” — you know, like co-going to a movie, co-going to a concert, co-walking on the beach and looking at the sunset. And if we’re being honest, it’s a lot more fun to co-stuff with a guy or a gal that we’re actually into. My mom and my girlfriends are fun, but come on — snuggling up on the beach is way more fun with someone you like making out with. Really, it is.

So, now what?!

After the shock and sadness about my own divorce wore off and the realization that I might actually want another man in my life sunk in, I did what most normal, intelligent women would do: I read all the blogs, the how to’s, the don’ts/do’s, and officially got my online dating account set up. Unfortunately after going at it, I systematically failed the how to’s and dove right into the don’ts and do’s. So here are a few of my failures. Learn from them, people! This is why I am here: to fail miserably at things so you don’t have to! It’s my sacrifice, so don’t waste it.

1. Do: Date men who are the opposite of your ex-husband

I made the mistake of dating men like my ex-husband, specifically the version of my ex from when we both actually liked each other. The chances that those men will eventually turn into the man I divorced are, you guessed it, pretty high.

2. Don’t: Get into a virtual, texting relationship before meeting them first

As I sit here, I am literally being text-stalked by a guy who is very upset because I wouldn’t send him a sexy selfie and talk dirty to him in the first five minutes of our text conversation.

It’s easy to have happen: You text each other to say hello and then, well, you both get carried away. We all enjoy good banter and more often than not, people are a lot funnier while texting than in person. But then you show up at the date and he’s not what you expected, and you’re not what he expected, and it’s awkward and everybody just wasted a whole bunch of time.

Here’s the deal: Set a time and place to have a short and sweet meet-n-greet before going text-crazy.

3. Do: Meet for coffee or an early drink

It’s never a good idea to meet them at 11 o’clock at night after you’ve both been out with friends and have probably had too much wine. That just ends badly. Picture my 5’2” frame carrying some drunk 6’4″ guy I just met to his car while he tries to make out with me. And to make matters worse, he texts me the next day and says, “Wow, that was really anti-climatic.” Really, you think?!

If coffee or an early drink works out, then hey, there are bars open all night. And if it doesn’t, you can make a quick getaway and go on with your life. 

4. Don’t: Date outside of your age group

If you’re 43 and they are 33, chances are they aren’t looking for a relationship. If you’re looking for one, look elsewhere.

Cue my story of being text-stalked by a 32-year-old. I was flattered, I’ll admit it. But most 30- to 40-year-old men who are asking out a woman 6-10 years their senior are either looking for a quickie and think you’re a desperate cougar, or clearly only checked out your profile pic, and since you’re hot and look young, just figured you were game.

5. Do: Read all the information they post about themselves on their online dating profile

Seriously, read it twice and take notes. Don’t think, “Well, he was hot and who actually reads those things, right?” Wrong. Trust me, learning is invaluable. I once invited a guy currently in AA to a bar, I went out with a hardcore Christian who about lost his martini when I told him about my days in the porn industry, and my pièce de résistance was sending a very crude joke via text to one guy, thinking it was another guy who said he loves to tell crude jokes, only to find out I sent it to the wrong guy… and that guy didn’t think it was very funny. (Also, note the “don’t text if you haven’t met yet” rule.)

6. Don’t: Plan your wedding, name your kids, and pick out a house after the first phone chat

I mean, at least see if they match their profile picture first! I know it’s a tough thing to accept, but sadly, my dear, it’s time to put away the glass slippers and put on some good walking shoes. When looking for the true Prince Charming, a girl should be realistic. Your life is not a fairytale and you are not Cinderella. Sigh.

7. Do: Be clear about what you want

Take a quiz, make a list, or do something else that helps you figure out what you want in a relationship, and then go for that. 

Please don’t go out with guys who don’t match that list and then end up wondering why they didn’t call. They didn’t call because they weren’t right, and at least they had the wherewithal to know that! And when I say make a list, I don’t mean put a picture of Ryan Gosling on your fridge and hope for the best. I mean know yourself and who you want to have in your life.

I could go on and on, but here’s the overarching lesson of what I’ve learned after three years in the “divorced, with kids, and over 40” dating pool:

Everybody pretty much sucks at it.

We’re all nervous, we’re all uncomfortable, and we’re all scared to death. We’re all a bit bruised and our self-esteem may be low, but we all deserve to be loved. Your love is out there. You may have to kiss a few frogs as they say, but you’ll find the one when you least expect it. So have fun, laugh at yourself, and don’t take the follies too seriously, because life would be pretty boring without them.

To read more of Betsy’s journey, pick up a copy of Tipping Sacred Cows, available now.

Article Posted 3 years Ago

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