Rosie O'Donell Dishes Out Love Advice!


Rosie O'Donell Dishes Out Love Advice!
Rosie O'Donell a love guru? Find out how.

A few years ago, the tabloids were all over it when Rosie O'Donell's marriage to Kelli failed. Although this may be old news, there are important messages we can learn from Rosie's divorce. The overriding message is loud and clear: Don't forge a relationship with someone whose background and interests are too different from your own. Their marriage was successful when Rosie was busy with her talk show. But, when she retired from the show to spend more time with her family, the differences between her and Kelli became insurmountable. I'll outline how you can identify key incompatibilities before you fall for the wrong partner.

Here’s how Rosie tells it in the October 2011 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.”

I love that. Don't you agree that there is so much beauty in imperfection? Rosie was attracted to the perfection she thought was missing in her life, only to later become repelled by that very same thing. Keep that in mind when you find yourself attracted to a man or woman who has something you think you need to "complete" you.

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, kindness, 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 don't believe in God?
  • 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.

Article contributed by
Advanced Member

Sandy Weiner

Dating Coach

Sandy Weiner

For a copy of my FREE guide, “The Top Three Mistakes Midlife Daters Make (and how to turn them around to find love now)” please click here.

If you are serious about finding love this year, there’s nothing like group coaching to keep you accountable and give you solid dating tools that work. In the Last First Date Inner Circle, you'll have access to two monthly topic-based Q & A calls about dating over 40, and a private forum for you to connect and share your experiences. All calls are recorded and transcribed, and you get a free chapter a month of my upcoming book. If you're a woman over 40 and want ongoing coaching support at an affordable rate, check out the LFD Inner Circle today. 

Location: Stamford, CT
Credentials: ACC, CPCC
Specialties: Dating/Being Single Support, Empowering Women, Online Dating
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