How to Date Like a Boss Post-Divorce

“Dating Post-Divorce”

Does that phrase fill you with horror? Make you want to run to the fridge and eat a quart of ice cream? If you’re like many women who find themselves newly single after a divorce, you’re not alone. But I’m here to tell you, girls, there’s a whole other perspective and you should really get on board with it. The beauty in dating again is that you now have new opportunities to have some “firsts” you thought were over once you married. You get another chance to fall in love. You get another chance to have that first kiss. What you thought was in your past is now in your future.

Dating at this juncture, with the wisdom and confidence you’ve gained now that you’re at the 50-yard line of your life (I’d much rather use a football analogy than the term “middle-aged”), you’re in a great position. You’ve already been the bride, had the kid(s), and all that picket fence stuff. You’re not fighting the biological clock of panic that would give you internal pressure to date in haste. Nor do you have to withstand the passive-aggressive “musings” of well-meaning people who want you to get married already. You’ve already been married – been there, done that. You survived The Big D.

Don’t be a martyr. If you’re doing the “Well, I’ll start dating once my kids are out of the house, and they don’t need me anymore” thing, chances are you’re a martyr. It’s a convenient shield that you’ve set up for yourself so that you have an excuse to not get back out there. You’re too afraid of rejection; you fear not knowing what to say or do on a date; you feel insecure about yourself. But you’re not doing yourself any favors. If you don’t want to date because you truly don’t want to, that’s one thing, but to not date out of fear, that’s something else. I always say, and it applies amply here, “The thing you’re afraid of the most is the thing you should do first.” Don’t do anything – or avoid anything – out of fear. Ever.

It’s now time for YOU.

If your kids are grown and out of the house, it’s much easier to date post-divorce. But even if you have a minor at home – like I do – take advantage of your downtime away from the kids to get out there and live a little. One day your kidzillas will be out of the house anyway – and then what?

What does “Date Like a Boss” mean? It’s something I made up that says, “Date from a place of strength.” Be a leader in the choices you make. Don’t fawn over a man who doesn’t treat you the way you deserve to be treated or put up with behavior that brings you down. The late Maya Angelou said something that I now live by:

“Never make someone a priority when all you are to them is an option.”

Date from a position of assertiveness that doesn’t allow for a lot of BS to enter your life. Date like you’re in charge of your own destiny … because you are!

Before you start dating, however, you need to be honest with yourself about what you want. Are you looking to get married again? Are you looking to have a committed partner? Are you looking to play the field (safely, of course)? Or are you just looking for a few dinner dates along the way? Whatever it is you’re looking for, operate from that truth. It’s up to you to use your best judgment about what you truly want and when to start dating. There are no hard and fast rules to follow for getting back into the dating game.

In the nearly two years since I filed for divorce, and just over a year since my divorce has been final, I’ve done some, shall we say, research on the subject of post-divorce dating. I’m happy to share my “boots on the ground” experience of what it’s like to start dating again.

5 Tips for Dating After a Divorce

  1. Don’t Be Crazy Bitch – Don’t unload on your date about how your ex is a jerk or about your custody battle or how you’re SO glad you no longer have to deal with his family and oh, my GAWD his Aunt Muriel is the worst. Yes, divorce can be hard – but your divorce is over. Don’t be bitter, at least not while on a date. Nobody wants to break bread with THAT, so leave your inner bitch at home.
  2. Try Online Dating – No, really! Not only is online dating a convenient way to be introduced to men you most likely would never meet otherwise, it’s empowering. It’s completely anonymous and you have the ability to say, “Move it along, Mister!” with the click of a button when a potential match turns out to be a dud. If you happen to meet a match in person, you can still say “Next!” when you finally meet face-to-face and you see very quickly that he’s emphatically NOT the one. Trust me – I’ve put my share of toe tags on guys right after we’ve gotten the check. When you meet a guy online, you have the privacy to be honest about what you really want – to express your needs or dislikes without the awkwardness of saying it to him in person. You can get all of the preliminary chatter out of the way to even decide if you want to meet him. Online dating is a good exercise that can prove to be beneficial. It’s a great way to test the water and get your dating IQ in top form. And you may even meet someone wonderful.
  3. Mix It Up a Little – Get a makeover. Buy some new clothes. Add whatever little touches you want to put an extra spring in your step. It’ll help build your confidence.
  4. Play the Field – This ain’t your grandma’s blog, so we’re gonna keep it real, girls. Do what’s best for you and your life. If you want to sow some wild oats, then get to sowin’ (again, with caution). Maybe you married young and you never really got the chance to date much. Or you just feel like it. Live a little. Enjoy. You’re welcome!
  5. Leave Your Kids Out of It – This is a personal choice for each mom. But if you can, try to avoid your children meeting your dates when it’s early in the process. When the time is right, when you want them to know someone you think is special, open that door then.

Ladies, you’ve reached a precious point in your life. You are at a new, exciting fork in the road. You can go north, south, east or west. You have unique strengths that have made you who you are and a level of confidence that you’ve built, whether you realize that or not. Get out there and have some fun.

Date because you can.


Date to find the one.

But whatever you do, date like a boss.

Wendy Allen

A native of Northern California, Wendy left home at 18 to attend Cal State Northridge in 1986, where she earned a BA degree in Radio/TV/Film Production. Three years later, she began an 18-year career in Hollywood, working at Paramount Pictures in the high-impact television industry. After working on hit sitcoms such as "Wings" and "Becker," she decided to put her talents into marketing and public relations when she relocated to Orange County, CA. Wendy quickly became known as a results-driven marketing professional who increased her clients' profitability through the creation and implementation of highly-focused marketing strategies. A busy mom of a teenage son, Wendy juggles a thriving career with her life as a proud basketball mom. In her spare time, she enjoys reading, cooking and spending quality time with friends and family.

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    Another great article, Wendy ~ offering a healthy perspective on dating post-Divorce; or simply for any single woman or mom, looking to dip their toe back in the water. And the bonus is that it’s an enjoyable read (single and married alike)!

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    I forwarded your article to a few friends and one came back with this: “The girl is so right on all counts. She might want to add that after awhile they might get tired of the dating BS and it’s OK to take a break when that happens so if Mr. Right should come along, you would recognize him and not place him on the do not touch list out of habit.” :o)

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    Great article Wendy! I know a bunch of women that would enjoy reading this. Especially the part about “Dating like a Boss” while doing the Online Dating thing. I really enjoyed that part. 🙂

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    Love this article! Just the right mix of humor, sass, and kick in the pants. I really like how you talk about not waiting until the kids leave the nest to start living again. I think as women we are always waiting to do something for ourselves when… Before you know it the when turns into never or too late. Thanks for the insight Wendy and I hope you find that man that makes you a priority!

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    I needed this article 16 years ago when I divorced and thought I had a Scarlett letter written on my forehead.

    Great Job! Keep up the good work, empowering us women.☺️

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    Excellent article! Great advice I wish I had about 27 years ago. My son’s father moved out right after he was born while I was still in the hospital after having a very difficult birth where we both almost died. Although I have dated a little bit, my challenge has been finding a gentleman who does not mind the fact that I am a preacher.

    Thanks for sharing your wisdom with us!!

    Love you!!

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    Excellent article offering a fresh perspective on a challenge many women face after divorce. Take charge and enjoy your life… Date Like a Boss!

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