Eavesdrop on a couple of boomers talking about dating and you’ll likely hear a laundry list of what’s wrong with the person they’re dating. While there’s no preventative magic, those lists can be shrunk and sometimes eliminated. A second date for a boomer should depend on whether their date on the first exhibited a fair amount of relationship potential, and a coffee date can be very telling if you know what questions to ask.

The stakes are too high to settle but the clock is running. Dating smart means narrowing the field rapidly to save time and energy. There’ll always be issues in a relationship that require compromise, but since the answers to these questions indicate basic, interpersonal skills no latitude is necessary.

A long dating dry spell can contribute to fantasies and projections about a first date based on little useful information, a lot of hope, and a powerful drive to be in a relationship again. There are five questions, and the best three or four out of five won’t work since all five are reasonable and fair to any boomer who’s done some amount of inner work. Dating is the time to be your own best friend, and staying focused is acting in that manner.

1. What’s Under The Hood?

Has your date done any type of personal growth work, individual or group therapy, been in a men’s or women’s group, attended any workshops or lectures about personal growth or relationships, read any books or magazine articles about relationships, or done anything at all that indicates the ability to co-create a successful relationship? This is critical since every relationship faces challenges. Knowing how to work through them is learned behavior. These skills aren’t second nature to many people, but a boomer who’s done some amount of inner work knows how to resolve issues.

2. Friends Matter

Does your date have any same sex friends? It’s important because it points to trust. A boomer without close friends may have unresolved trust issues that will become problematic later. My mentor said it well, “Where there’s no trust, there’s no love.” In addition, dating a loner means you’ll automatically become his or her entire universe, an onerous burden. Having close friends also suggests the presence of relationship skills since friendships sometimes have issues that need to be resolved. The best relationships are also best friendships, but that depends on a willingness to trust and be trustworthy.

3. Boring?

Did your date show interest in you and your life? Did he or she ask you a fair number of questions? A frequent complaint is a first date that didn't stop talking about his or her life and failed to ask their date anything about theirs. This is a red flag because it suggests someone self-involved, and self-involved people don't make good partners for obvious reasons. There are no excuses for rudeness, and a second date will only confirm your date wasn’t a good prospect.

4. Generosity? Maybe Not

Does your date have some means of support? Unless you’re okay with financing the relationship, this matters. And, the inequality of badly lopsided financial relationships rarely works. I’ve seen many boomer relationships based on one person supporting the other and few succeeded, in part because there’s nearly always the expectation of a quid pro quo, whether verbalized or not. While this doesn’t apply to married couples, in general there’s no free lunch.

5. Hot Or Not

Physical chemistry is vital, but I'm not suggesting sex too early in a relationship. It’s a good idea not to become sexual until both partners feel confident the relationship is viable. It helps avoid the hurt feelings that accompany rocket ride, failed relationships. Since the great majority of couples feel that a satisfying relationship embodies strong physical chemistry, it’s worth asking your date how important they feel it is. Don't sell passion and heat short. Relationships are difficult enough, and one lacking in juiciness is off to a shaky start.

If you’re skeptical or shy about asking these questions, think how you’ll feel after wasting months with someone inappropriate when you might have discovered their issues simply by being up front and honest. My coffee dates were always grateful and I was glad that most turned my questions around on me. The nature of our answers told us far more about each other than we could have learned chatting about lesser things. Whether or not to have a second date will be much more clear, and the only people who might find these questions objectionable likely can’t answer them well.

Of course there are other factors involved in determining a first date's second date potential, and these questions aren’t going to work perfectly every time. But everyone wants to meet someone who can hold up his or her emotional end of a relationship. These questions point in that direction.

Photo Credit: Kannan B via: imager.io, cc

Ken Solin is a Dating Expert who has written about boomer sex, dating, and relationships for The Huffington Post, AARP, About.com, and Maria Shriver for a decade. Ken believes boomer women are perfect for boomer men as he discussed on The Today Show.

Ken's new book, The Boomer Guide To Finding True Love Online, is available for preorder at Amazon.com. It offers real-life boomer dating solutions based on Ken's online dating experiences and the experiences of tens of thousands of readers who have commented on his articles. His relationship philosophy is simple. "You can't think your way through a relationship. You have to feel your way."

Read Ken's articles at www.kensolin.com and visit him on Facebook.