Love Lessons from Rosie O’Donnell

Posted by in dating after divorce, self-esteem in dating, single women over 40 | 0 comments

Rosie didn’t actually teach any love lessons outright in her ‘O’ interview in October’s Oprah Magazine. As a dating coach, I can’t help but see the hidden messages in almost everything I read. To me, the message is loud and clear: Don’t marry someone whose background and interests are too different from your own. Rosie and Kelli’s marriage worked well when Rosie was busy with her talk show. But, when Rosie retired from the show to spend more time with her family, the differences between her and Kelli became insurmountable. Find out how you can identify those incompatibilities before you say ‘I do’.

Here’s how Rosie tells it in Oprah Magazine: “Kelli came from a very debutante ball kind of family. It was like a life out of Dallas. All the photos in her house were of her family in the same outfits at the beach — which, to me, looked fake. But when I’d send pictures of the kids to Kelli’s mother, she’d say to Kelli, “Why does she take the pictures when they have chocolate on their faces?

There was a time when I wanted the porcelain veneer. But as I grew up, I realized, wow, the beauty is in the cracks.”

Rosie was attracted to something she thought was missing in her life, only to find out that she was later repeled by that very thing. Keep that in mind when you find yourself attracted to a man who has something you think you need to balance your life.

I was always attracted to men who set clear limits, something that was missing from my home life growing up. I ended up with judgmental, rigid men, which didn’t work for me at all. I learned that limits are important, but only when balanced with love and respect. 

Here’s more from Rosie: “It wasn’t clicking for either one of us. We didn’t like the same stuff. I’d go out on my boat –I could spend ten hours a day on my boat (with my kids), looking for dolphins, but Kelli didn’t like the boat or the pool. She liked tennis.

When the separate interests became day after day, I found myself lonely — as she did, too.”

When you’re dating, it’s easy to overlook these ‘separate interests’ as insignificant. 

How important is it to marry someone with similar interests and a similar background? 

It’s one of the key areas of compatibility. Throughout the day, you make tons of decisions with your partner.

Do you like the house cold or hot?

Do you like meat or vegetarian cuisine?

Do you go to church or synagogue or like to stay home?

Couch potato or physically active?

Modern or antique furniture?

The more you have in common, the easier your lives will flow. The more dissonance, the more fights you’re likely to have. Or even worse, like Rosie, the more lonely you’ll feel in your relationship.

So don’t underestimate the importance of common interests. You’re not being too picky if you move on to someone who likes more of the same kinds of things you do, someone who wants to do the same things on the weekends. That is not shallow at all.

It’s actually a sign of alliance of core values. In Rosie and Kelli’s case, there are different values one gleans from shopping and tennis over counting dolphins from a boat with your kids.

Your values are an extension of you. Pay close attention to what matters to you, and you’ll attract a man who believes in the same things. Otherwise, you’re working too hard to try and make the relationship successful.

Those incompatibilities will come back to haunt you.

I know it. I lived it. And I vow not to repeat the same mistakes.

I’ve made mistakes in love so you don’t have to. I’m here to help you figure out the difference between a true incompatibility and an annoying habit. Don’t hesitate to ask for help. That’s what I’m here for.



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