You CAN Find a Date Worth Keeping

You Can Find a Date Worth Keeping – Dating Strategies from a woman who has only ever gone on 7 first dates her entire life... and why THAT is a VERY good thing!

Annie Allen< Certified Divorce and Life Transition Coach


I want to talk with you today about dating. It is a subject of course that is of great interest to anyone who is even thinking about divorce, or definitely going or having gone through divorce.



We recently heard here on the show from a divorce attorney who said the #1 question she gets asked by clients and potential clients alike is “can I date during divorce?” If you missed the Questions People Ask their Divorce Attorney episode a couple weeks ago, you will want to go back and check that out. We had some great ideas about dating and about communicating well with your attorney to lower your divorce costs.


And when her and I talked about that #1 question it reminded me of something I have talked through with many of my coaching clients and I wanted to share just a little bit about my dating experience so you can learn a little bit more about what this part of your life could and maybe should look like.


Should you date?

Should you even be thinking about dating?

Are you actually already dating and just looking for someone to give you permission?

What is your motive for wanting to date?

Do you just want to satisfy some primal urges?

Do you want to find the one so you don’t have to spend any time at all alone?

Are you trying to avoid being alone with your own thoughts?

Here are the really important questions:

What wounds are you still carrying in your heart and mind from your marriage?

Were you cheated on?

Abandoned? Neglected? Abused? Ignored? Blamed? Shamed?

Have you shut down that part of your heart and mind that knows some of these wounds do exist inside of you but you don’t want to deal with?


OR have you spent some focused and intentional time in therapy or working with a coach to find the roots of your wounds from a broken marriage or even all the way back to childhood that may very well have led you to pick the mate you did in your first marriage?

Do you feel like you’ve done the work? Or at least 90% of it, to discover the real you?


HERE is the real question as you think about dating... is the current condition of your heart and mind what you want when you meet someone that could be a future mate for you? Are you your "best self" out in the world of single people where your potential second chance at love could be?


I jokingly tell people that you will know you are ready to attract the love you are desiring when you’re only half sure you want to date. The other half of you is so happy and content as your best self, living the single life, building or maintain your career, being wholly present for your kids and/or grandkids, enjoying hobbies, loving your alone time so much that you’re thinking, “Ok, I will go on some dates, but these people are really going to have to have something pretty darn special to offer to be the icing on this cake you’ve made of your new life!”


This is exactly how I approached dating after the dust was settled on my divorce. (I had no desire before then.)


After spending three decades with the only man I thought I would ever love, from the age of 14 to 44, my divorce ushered me into a season where I found myself facing the prospect of dating for the first time in my entire life. So when I got on some apps and started going out to meet new people, I did it because I thought to myself “Well, I guess better practice on some people so I can learn HOW to date.” Since I had never done it before with anyone but my ex and one guy for one date when I was 20 (24 years previous!), I was clueless.


I remember thinking, and this is something I know tell my clients, I’m not playing games. I will do my hair and makeup because I do that pretty much anywhere I go, but I am not buying a bunch of fancy clothes or acting in a certain way. I ended a marriage to be able to be who I am and I am not changing that now. I am just going to be me. If this guy is “the one,” he will like the real me, good and bad. And if he is not the one, I hope I do scare him off because I don’t want him. I don’t want anyone that is attracted to a fluffed up, inauthentic version of me. That, my friends, is a really good place to start. So I would say the first step in finding a date worth keeping is:


#1: Start dating when you can date authentically.

I admit I had no idea how to date, but what I am saying is that I think that is an advantage. Dating in many ways is a lot of pretense for a lot of people and that’s why they’re all so frustrated. You don’t need that. You’ll be miserable if you try to date that way.


What I DID know was where to get the help I needed to put it all together. So with some coaching from my therapist, the help of a good book, and just following my own intuition, I unwittingly created a dating strategy that yielded the love of my new life on the seventh date of my life. In my 45 years of living, I went on a date on October 25th of 2018. The seventh date of my life, and by that I mean, when I was young I went on my first date ever with the man I ended up marrying. When he and I broke up once before we got engaged, I went on the 2nd date of my life which was a totally bad boy experience that I told myself I just needed to get my then-ex out of my head. It was never going to be more than that one date.

Then 24 years later, when I had married and then divorced after 22 years, I went on a date every other month or so, four first and only dates with guys I met on different dating apps. They were all never going to be more than just one date. I didn’t even kiss the vast majority of them.

I enjoyed going on dates. I like meeting new people. I was always okay with knowing this next guy may not be the one, but we can still have a nice meal or conversation. And so that’s what I did, and that would be my second tip for finding a date worth keeping.


#2: Approach dating casually as simply a way to meet new people and have enjoyable experiences. Not a fevered and frustrating search for THE ONE.

When I went on the 7th first date of my life, it was with the man I am engaged to marry today. A man who knew from the moment he laid eyes on me that he was going to want to spend forever with me. (And I knew it that night too.) He has loved me unconditionally for who I am. He is a good man who works hard and loves even harder. He is humble, he is a good listener, and he cares how he makes me feel. He apologizes when he hurts me and wants to understand what he can do better—and then SHOCKER of all shockers—he actually stops doing things that he says he won’t do anymore. He loves God and he isn’t religious. He hustles to make ends meet with me. He even cleans the house, helps with laundry and cooks dinner—probably more often than me! (Ok, definitely more often than me!)

So how did I attract such a perfectly aligned and amazing partner with little to no knowledge about dating? Am I just that lucky? No, I definitely am not lucky. If you know anything about my life, you know that. This was not a happy accident. It was intentional and you can do it too.


And you know what else? I think not knowing anything about dating may be what actually helped me. Having no idea "how dating was done" I had to just be me and do what felt right.

And I did have a little bit of a strategy to it. That’s just how I approach everything in my life. A plan just comes together in my mind as I act and so it was with this, that it was really only with hindsight that I could tell you how I got from where I was to where I am—with a date worth keeping!

BUT HERE’S THE DEAL! I am currently working on developing a mini e-course on Finding a Date Worth Keeping that will be available here on the Starting Over Stronger website, and in that course I am going to teach you every little detail of the effective and enjoyable approach I took to dating with intention, that I like to call Dating Baseball (and it's not the second base you might be thinking of) but for now I am going to get you started thinking about how you approach dating and whether or not it is working well for you. Spoiler alert: if it was, you probably wouldn’t still be dating, right!?


I am now sharing how I created a dating plan that worked perfectly for me, and I think you will find that it will work well for you too. I can't promise you will find the love of your new life inside of 7 dates, but I also can't say that won't happen either!!!


I do know this:

1. These strategies work

2. These strategies will give you confidence.

3. These strategies will have you ready to meet new people, trusting your instincts, and detaching from outcomes while just enjoying life more.


Just imagine how attractive that is going to be to the one who will come ready to love you the way you need and want to be loved!!!!


I know this part won’t shock you! The top 3 strategies involve journaling! And you are going to have to listen to this week's episode of the podcast and take good notes to learn how to apply them in your search of a date worth keeping. I will give you a hint. The three steps involve:

1. Looking back in the rear view mirror to the past you want to walk out of

2. Looking forward through the windshield to what you want the future to look like

3. Looking within the map inside of you to how to attract the love your desire.


I will explain each of these journaling techniques in detail on the show and I hope this will inspire you to think below the surface about what dating means for you and what it could bring into your life. It’s all horror stories out there for those who don’t bring this kind of intentionality to the table before they jump on the apps and start booking dinners.


As always, even in dating, there is help and hope for those who seek it. Reach out and get the help you need to have hope.






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