boomer dating, dating after divorceHave you seen the movie, “Enough Said”? If you didn’t see it in the movie theaters and you’re dating after divorce, I suggest you rent it today. It’s a terrific study on how to make sense of dating in midlife post-divorce.

Eva (Julia Louis Dreyfus), a divorced single mom, is a traveling masseuse. She brings her massage table to her clients’ homes. Her only child is leaving for college in a few weeks, and she is struggling with separation anxiety. She attends a party where she meets Albert (the great James Gandolfini, may he rest in peace); a funny sweetheart of a man whose only daughter is also about to leave for college. They’re both surprised to find how much they have in common, and an endearing romance slowly blossoms.

The plot thickens as Eva befriends Marianne (Catherine Keener), her newest massage client. Marianne, a beautiful blonde poet, complains incessantly about her ex-husband. As Eva learns who Marianne’s ex is, Eva finds herself beginning to doubt her attraction to Albert.

Without giving away too much, I’ll just say that this movie is an insightful story about what happens when you ask too many people what they think of the person you’re dating after your divorce. Many of the issues that Albert and Eva are dealing with are similar to the ones my clients are struggling with as they try to make sense of dating after divorce.

Making Sense of Dating After Divorce

Dating after divorce is not exactly the same as dating in your twenties. If you go in with the right expectations, you’ll have much greater success. Here are some of the key differences:

1. You expect me to go out with HIM? People look different in midlife. Albert is overweight and balding. Eva doesn’t find him attractive at first. But once she gets to know him, she finds him to be very sexy. Be open to how love may show up in your life this time around. Don’t expect him or her to look like your twenty-five year old idea of attractive. Course-correct for middle age, and you’ll be able to see the hidden beauty in each person. As your love grows with the right partner, he/she becomes even more attractive.

2. What about the kids? If you have kids, you need to be mindful of them as you embark on having a dating life of your own. When do you introduce them to your new love? Do you have sleepovers when they’re home? What messages are you broadcasting if you’re having sex but don’t want them to? It’s important to consider all of this when dating after your divorce with kids in the house. My recommendation is that you don’t introduce your kids to anyone you’re dating until a relationship is well under way and this person seems like a keeper. Younger kids are at risk for becoming attached and then devastated when you break up. They don’t need to be privy to the revolving door of dates/lovers in your life.

3. Stop comparing! The movie became complicated when Eva stopped trusting how she felt about Albert and began believing the opinions of others. She became confused about her conflicting emotions, and started questioning her attraction to Albert. Your relationship between you and your significant other is only about the two of you. The dynamics with his/her ex were different. Unless there was abuse or danger of any kind, I believe you should trust your intuition about how you feel when you’re with your partner. Are you falling in love? Do you like him/her for who they are right now? Go with your gut. It’s usually spot on.

I hope you watch ‘Enough Said’. It represents the complexity of dating after divorce with humor, insight, and grace. What are your biggest challenges in dating after divorce?


If you want to find love this year, there’s nothing like group coaching to keep you accountable and give you dating tools that work. The Last First Date Inner Circle is a warm group of lovely women. We have two monthly topic-based Q & A calls about dating over 40, and a private forum for women to connect and share their experiences. All calls are recorded and transcribed, and you get a free chapter a month of my upcoming book. This month, we’re talking about the art of flirting with flair. Check it out here.

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