THE BLOG
10/25/2013 10:00 pm ET Updated Dec 25, 2013

Clarifying Questions for the Newly Single Grey Divorce Set

With the surge of grey divorce there are a number of newly single over-40 men and women who are dating again for the first time in a while. These new singles may bring along either heavy-lifting "baggage," or hopefully lighter "luggage," either of which will be meaningful to you should you get into a relationship. If you're contemplating dating a newly minted middle-aged single person, or if you are one, when the time feels right to start dating again, there are a few things to keep in mind.

Only a portion of what is going on with you or another person is obvious on the surface. Imagine if you could gather information and therefore pay more attention to the depth of another person, so that you can better ascertain if there's a fit early on. Well-placed and well-intentioned questions may help as you get to know them.

These less obvious are questions and thoughts better kept to yourself silently, if you can, at first. If you can't keep them to yourself, then accept it's your "authentic" self yearning to be heard and taken seriously. Be gentle with your own and your date's vulnerabilities. Remember after a break up most people run from judgments. They feel both free and broken and most of all entitled to another chance at happiness with a new partner that could be you.

In any case, whether you remain quietly observant or verbal watch your date's meta-communication behaviors and body-language responses carefully, taking into account respiration, eye-contact and speech pattern. Try to hear and accept their words but verify their intentions with actions.

Each category of questions moves from less intimate to more. It would be wise not to dive into the last questions first unless it seems natural to do so. The first and third category of questions below are the biggies and contain a treasure trove of information in deciding if this is a relationship to pursue. The middle question is informational and more about potential compatibility in terms of daily routines and regular habits.

The order in which these questions roll out is up to you. All three can be in play simultaneously. Are there too many red flags with any of these questions? If so, bow out as gracefully as possible while you can.

1.Foundational Questions: How long have you been single? How much therapy have you had? Are you in therapy now or at other times in your life? What's your support system been like in your divorce? Who are the players? How long did you think about divorce before the plug was pulled? Did you have doubts about your marriage walking down the aisle? To what extent did infidelity play a role in the demise of your marriage? When did things turn from good to bad? Do people consider you difficult or easy to get along with?

You may want to go even deeper into the past, especially if you're going to meet your date's family and friends. Remember even the best relationships are 'under management' and require maintenance. Like your own life, chances are theirs too is some mixture of a bittersweet work in progress. You need to hear what's good as well as what's getting better. What's good and not so good in a person's support system and family of origin is likely to be mirrored in your dating relationship.

Should you advance to these functions know that you will be tested. What's working out with your dates parents is only the start. There are also in-laws and half- and step-children with who you'll be in relationship to.

2. Aggregate Questions: What are your rituals around eating a sleeping? Are you a morning or night person? (Do you floss your teeth in bed? Do you prefer to bathe in the morning or night? Here I'm kind of kidding.) What was the name of and last time that you read a book? How many hours a week do you work, watch sports or business news on television? What's your faith practice? How about playing video or computer games and hanging out on the Internet? Do you watch or participate in porn? What are your hobbies? Where do you like to vacation?

3. Kicker Questions: Who else thinks you are their significant other? A dear friend alerted me to this one. You would think that a person is on the market only if they are truly free, but this isn't always the case when someone is newly single and is trying out dating for the first time in a long time.

The other possibility is the person who appears free may be in fact in an ambivalent break up. Chances are they may still make love to their former partners or co-parent from time to time or on a regular basis. Are they in therapy with their ex? Perhaps your date can't tell you, but will show you and maybe tell you if you ask the right way.

With all of these questions, listen hard and watch closely for what is revealed and hidden. What is the other willing to tell you, if you can catch it?

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