November 25, 2014

Dating Doesn’t End at 20: Some Pointers for the Older Folk.


Photo: Chandra Wirawan

I never thought I’d be dating again at 49 years old.

I thought I would be married to my high school sweetheart—if I thought about it at all.

Actually, I didn’t think much beyond when I wanted to be married (25) and when we would have kids (first at 28, second at 32 and done). I believed life moved linearly: you fall in love, you get married, have kids, retire, buy a Winnebago and die a peaceful death, preferably in sleep.

All that changed when I was 24, when I called off my engagement, moved out of our shared home, and I was faced with dating, for the first time, as an adult. I spent my 20’s backing into relationships. If someone was cute, and they asked, I’d date them, while waiting for six years someone who was unwilling to commit to me to wake up and see that I was wonderful.

And then I met my husband. After our second date, I knew he was the one for me, and no one could talk me out of it. Not even him. After three years together (the first two with him trying to break up with me every three months and me talking him out of it), we were married.

The search was over. I found my life partner. We bought a house and had two wonderful kids.

Well, that breaking up thing? Although it stopped happening out loud, apparently it was still going on inside of him. After almost a year of counseling and another year of separation, the marriage was over.

I was profoundly disillusioned. I’d gotten everything I wanted—husband, kids, house, dog, cats—and here I was, alone again.

So I jumped straight back into dating, looking for validation externally that I was lovable. Dating people who weren’t appropriate—again. Waiting for four years for someone who was unable to commit to me to wake up and see how wonderful I am —again.

This time I added online dating to the mix going on lots of dates with lots of people. I could write a book on that adventure!

Looking back, I see now that I was living Bill Murray’s life in Groundhog Day.

And then it all changed. After my last relationship ended, I finally stopped searching for love and…I took a break. I stopped running from relationship to relationship. I didn’t think at all about dating. I spent my time focusing on my kids and my friends and my interests and my life.

And it has been really good.

But at my core, I am a romantic. I still believe in lifelong love. I still believe in happily ever after. But I know now that when you skip off into the sunset, it will get dark, there are rocks and divots and hidden branches on the path that will trip you up, and that it takes work to keep skipping until the sun comes back out again.

So here I am, looking at dating again.

At 49.

This time, things will be different, because my attitude is different. There is a great scene in one of my all-time favorite movies, “The Holiday”, between Iris and Arthur. While out to dinner, he says, “In the movies, we have leading ladies and we have the best friend. You, I can tell, are a leading lady, but for some reason, you are behaving like the best friend.”

She responds, “You’re so right. You’re supposed to be the leading lady of your own life, for God’s sake!”

I am a strong, independent woman who is perfectly capable of taking care of myself. I am the leading lady in my own life. So that I continue to honor myself as I start dating again, I have created guidelines for acceptable dating behavior that I will share with you.

So with the greatest respect and admiration for the men out there that might want to date me, and the women out there who are like me, here is what I’ve come up with:

When you ask me out for the first time, plan the date. Don’t rely on me to determine what we do. I have kids and a job, both of which expect me to make things happen so I do that every day, all day.

Even though I am a very strong, fiercely independent woman, it feels good to feel like someone else is taking care of something on my behalf. To feel like there is someone who wants to make my life a little better by his participation in it. Planning a date does this.

1) Open doors for me. Remind me that chivalry is not dead.

2) Look at me. Really take time to see all of me, not just my surface.

3) Always be honest. If you say you are separated, actually be separated. Not doing so is disrespectful to your date—and your wife. End the date and go home. Please. Or better yet, don’t call.

Honesty leads to trust. And without trust, there is no relationship.

4) Talk to me. Get to know me. And let me get to know you. I have lived an interesting life, as have you. Trust is created in the sharing. And where there’s trust, there’s fire (in the sack).

Speaking of sex…

5) Yeah, obviously both of us do it. And yeah, it can be a really great thing. And although I’m sure you have really great skills in the sack, but be patient. Keep them under wraps for a bit.

Get to know me before trying to move things forward.

I remember one date that was going very well. He was handsome, interesting, tri-lingual, polite and funny. Not only did he help me with my coat, he flipped my hair out from the collar, which was a first for me. He ticked off a lot in the “plus” column and I was looking forward to seeing him again—until the very end.

After a kiss and hug goodnight, he went for a boob.

Date over. Buh bye.

My booty call days are long gone. It’s not what I’m up to in my life these days. If that’s what you’re looking for, I refer you back to point number three.

So there you have it. I am excited to date again, with these self-honoring guidelines in place. I may not go out as often, but I will have fewer chapters to add to my Bad Date book. And that’s a good thing.

How are you living your dating life? Is it by default? What’s driving you to choose the people you choose to date? Is it time to create your own list? If my list resonates with you, I invite you to incorporate it into your life. Take what works, and discard the rest.

After all is said and done, you really are the leading lady of your own life.




The Number One Commandment of Dating.



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Author: Kendra Hackett

Editor: Renée Picard

Photo: Chandra Wirawan at Pixoto 


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