They say we learn more from our failures than we do from our experiences with sucess, and never has this statement been more accurate then when applied to dating. When everything is super easy you’re just riding that cocaine high and enjoying the good times together.  But when things become difficult, that is when you really see if the relationship can really go the distance.

Ever since I divorced my college sweetheart in 2005, I spent the better part of the past 17 years playing 20 questions.  Honestly, it was a great distraction when I wasn’t focused on work or raising my son.  I personally enjoy mapping people- it’s interesting to see where did they come from, where are they now, and where are they heading?  And if you enjoy similar activities, it’s very easy to get lost in the moment and just enjoy the present without thinking too far down the road as to whether you could ever settle down with this person.  Unfortunately, when you are busy having fun, precious time can fly by and before you even realize it you’ve spent months or perhaps years settling for Mr. Right Now instead of holding out for Mr. Right.  

This past decade started off with an engagement on my 40th birthday, and six months later I called it off.  Then I fell hard during a 2 year whirlwind romance with a Brazilian that ended abruptly 6 months after we started cohabitating and real life hit us hard.  After a long-term break from any boy-drama, I eventually met a doctor, who sadly turned into a stalker when I ended our 16 month relationship.  The authorities had to be involved, and honestly it has taken me a very long time to forgive myself for ever allowing that person into my life.    The only good thing that came out of that experience was that he introduced me to the game of golf, which has allowed me to meet an incredible group of friends during COVID and provided me a great escape the past two years.

One might think that after three huge fails I might take a break from playing 20 questions, but the reality is that as I approach this next decade I realize I want to share my life, both the highs and the lows, with someone special.  Over the past two decades, I’ve not only proven that I can take care of myself while raising a child, but there’s also no doubt that I have enjoyed life to the fullest along the way. Whatever it is that I needed to figure out on my own, I did it on my own terms, and for that I am eternally grateful.  But now, if I am being honest I don’t want to continue the journey alone and the desire to find a meaningful connection with a significant other is powerful. 

When you are done playing games, I promise you will know.  And as you begin to appreciate how precious time is, you won’t waste it on people that aren’t worthy of your company.  The right person will cross paths with you at the perfect time, and when s/he does you just need to be ready to make the most of that opportunity as scary as it might be because ultimately, we are not meant to be alone.

Life is better when shared with those you love, but the journey to finding your soulmate (which should not be confused with a playmate) may not be an easy one.  Maybe you have to appreciate how difficult it is to find the right person so that you won’t take him/her for granted once you do connect?  I wish I had all the answers, but I don’t.  I just know there’s no point in living with regret.  We have all made mistakes in the past, and they can’t be undone.  Grieve the loss, process it, learn the important lessons and move on. 

Now, as many of my close friends know this week I am about to complete my happiness project (50 nice things before turning 50), and the grand finale is this weekend.  Originally, it was supposed to be a golf getaway with friends, but as they say if you want to make God laugh, tell him what your plans are.  Let’s just say Divine Intervention has set in motion a recent turn of events that now has me bringing a plus 1, who is far more than just a playmate.

Ultimately, I can’t predict how the rest of this year, let alone how this next decade is going to unfold, but I can definitely say that I am done with the games.  There is nothing more precious to me than peace and serenity, especially after this past decade.  Each person will have to follow their own timeline, but sooner or later I encourage you to become more discerning in your dating life, especially when you find you’re done having fun and want to be serious about meeting your forever person.

By Regina A. DeMeo