09/30/2011 12:07 am ET | Updated Nov 29, 2011

Five Sure-Fire Dating Tips for Frog-Kissing Boomers

Dating can feel like a contact sport with the bruises on the inside, and it's an activity few boomers relish. With each mismatch, the pain takes longer to heal and there's less margin for error. Here's how you can avoid wasting time kissing frogs and hone in on your perfect boomer partner.

As a single, divorced boomer who dated for nearly 25 years, I believed that finding the woman of my dreams was a numbers game. If I kissed enough frogs I'd eventually discover my princess. I was sure this was true, because everyone said so.

I met and married my dream woman four years ago, and there wasn't any luck or frog-kissing involved. I asked her the right questions when we met, and she gave me all the right answers. Here's how it works.

You're on a first date in a cafe. You feel the chemistry. Your heartbeat quickens. Your fantasies are looping in your head like a movie trailer. Take a deep breath, look your date in the eye, and ask these questions. The answers will be a good barometer of the long-term possibilities of your relationship:

Have you ever been in individual or group therapy, attended a relationship workshop, been in a men's or women's group, or read any books about relationships? Relationships create problems, and anyone who has shown no prior interest in emotional awareness and growth probably won't have the skills to help work through issues that arise. A boomer who's had decades to work out emotional issues and is still unable to feel his or her own pain isn't going to be able to feel yours either. Since everyone occasionally needs emotional support, this is a non-starter for a healthy relationship.

Do you have a job, or some other means of supporting yourself? Becoming someone's life support system is unlikely to get your relationship off to a good start. Think about what carrying a partner financially would mean -- and what you would expect in return. This would be a lopsided relationship, with one person wielding most of the power. Not a good basis for building intimacy and trust.

Do you have any same-sex friends? A boomer without friends of the same sex is a major relationship risk. He or she typically has trust issues that get in the way of developing intimate relationships. Dating a friendless boomer also means you'll become his or her entire social universe -- a heavy, and impossible, burden to carry.

What spiritual, religious, or moral beliefs guide your life? Shared basic values and approaches to life are essential to the long-term success of a relationship. If your boomer date doesn't have or can't articulate what makes life meaningful, that's not a void you want to have to fill.

What did you learn from your last failed relationship? If your date hasn't learned anything or denies any responsibility for the break-up, get out of your chair and out the door quickly. A relationship involves two people, and both play a part if it doesn't work out. A boomer who still hasn't learned that it's okay to admit fault and be willing to learn from failure probably will blame you for any problems that arise. You deserve a partner who is emotionally open and healthy and who understands that admitting mistakes is not a sign of weakness.

So date smart. If you get promising answers to these basic questions, ask any others that are important to you. And don't settle for any inappropriate answers. Finding the right partner in your boomer years isn't a percentage game, and nothing less than 100 percent will do. You'll know whether or not your date has the potential to go the distance before you even finish your coffee.