The Top 10 Questions to Ask When You're Dating at Midlife

The Top 10 Questions to Ask When You're Dating at Midlife
by Susan Dunn, The Dating Coach

1. How much baggage is he carrying?

"Baggage" is different from life history. Baggage refers to serious unresolved problems -- an ex-wife he can't get over, betrayal by a business partner that has destroyed his trust, or an untreated depression. Nothing's carved in stone. It matters only if the man is stuck, or willing to move on. (Try referring them to coaching if stuck. Attitude can be changed, if circumstances cannot, as you know!)

2. His emotional intelligence.

My client Melinda was having trouble figuring out what was going on with the guy she was dating who was 10 years older than she was. She assumed someone older was also wiser, which is not the case. A person's emotional age can be much younger than their chronological age. If your intuition is telling you he's immature, he is, regardless of his chronological age. If you're in doubt, one session with an EQ coach can give you valuable information. EQ can always be advanced, BTW.

3. What does your intuition tell you?

Are you getting messages from your intuition? You should be. It's your most valuable guide. Intuition is an emotional intelligence competency. Everyone has it, and it can also be developed. An assessment like The EQ Map will tell you how good yours is, and EQ coaching can help you improve it. Intuition takes up where the data runs out, and we need it for the most important life decisions of the heart. (He may call it "gut feeling.") How will know he's the right one for you? Your intuition. Analyzing the data will notget you there.

4. How are his relationships with the rest of his family?

There are patterns in our lives that keep repeating themselves (unless there is intervention). If his children aren't speaking to him, or if they are calling him constantly and overly dependent on him, there's something wrong. The same things will likely occur in your relationship with him. For instance, if he tells you his daughter "defied" him and he kicked her out, what do you think lies ahead for you when you first "defy" him, I mean have a disagreement?

5. What is his relationship with his mother?

We all know to check this one, but don't overlook it.

6. What do you know about his former wife or wives?

Men are far less likely to change of broaden their tastes than women; in fact they are known to marry the same woman over and over again. You can find out what his "type" is and then anticipate the chances he'll marry you. You can also anticipate where the sore points may lie. Let's say you're dating a physician who has married two social workers, and you're a therapist. For some reason he's attracted to psychological-types, and for some reason it hasn't worked out. That reason why it hasn't worked out needs to be given a long, cold look. (Call a coach!) Unless he is willing to change his way of doing things, you and he will have the same outcome.

7. Where is he in his career?

A man who is ready to retire is often desperate for companionship. If his work has been his "life," it's a time of confusion and fear, and his need will border on desperation for something to cling to. It's not that you'd mind being a "lifesaver" temporarily, it's that he won't know his own mind, and yet will be very convincing. If you're getting a barrage of flowers and cards and he's talking about Fear of Retirement, give it time and look it over carefully.

8. How long has he been single?

My long experience in dating coaching confirms that a man in transition is not a good bet. Occasionally it works out, but not often. If he is "legally separated" or newly divorced, keep your thinking cap on. Men are likely to grab the first woman who comes along (who's willing). Their vulnerability and touching earnestness can make them deceptively attractive. You won't know you were being used until later on. Good coaches recommend their male clients in such a state date several women so as not to "lead them on." Lead them on to what? A man newly divorced is not ready for a new commitment. If you're just looking for a good time, he's your man (thought the ending will still be rough). If you want serious, and you get involved, you're likely to get your heart broken. Check it out with your coach if you're not sure what you're looking at. Men are not as creative in their response to life as women, and the patterns are quite recognizable to someone with experience.

9. What are his finances?

The state of a man's finances at mid-life can indicate patterns. For instance, if he's not been able to commit to a career or to a marriage, divorce takes its toll, and he's likely to be in dire straits financially. There are other reasons too, of course, such as bad luck, or being in field with natural ups and downs, like the stock market, so check it out. The money itself isn't the issue, it's how and why it happened. (The value of money to you is a personal decision). Decide what you want and need in this area, check out his situation, and then find out why he is where he is.

If he's well-heeled and ready for retirement, you will have a high-level problem. Likely he is about to grab a gal and cut loose. Is this you? In other words, what you see is not what you're going to get. If you have ties to kids in the States and he wants to go live in the mountains of Spain or spend a year at-sea on his yacht (as happened to one of my clients - the guy was ready to set sail for 12 months!), you'd best know this as soon as possible so you can make a decision.

10. Why are YOU dating?

In listening to people, and reading the online profiles, we see different points of view. While we assume in our 20s that men and women want the same thing in marriage, interests vary widely at midlife. A man may be impotent, for instance, and just want companionship, or twice-burned and determined never to marry again which might be fine with you, except what it really means is he will never love again. (I wish these men would come for coaching!) He may have his family all gathered around him and be planning to spend his later years playing with the grandkids, or want to live in the Bahamas and travel 6 months of the year. And what do you want? The main thing to figure out is his flexiblity (an emotional intelligence competency). Some people are quite willing to change plans with time, or for a loved one. Others are not. You need to know what you're looking at. If he's the kind who has been in the same profession for 40 years and lived in the same house for 30, and says he will work till he dies and never move, you'd best believe it.


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By Susan Dunn, MA, Clinical Psychology, Founding Member of Coachville, Life & EQ Coach, who can be reached at sdunn@susandunn.cc, or visited on the web. Susan Dunn wants you to know: Offering individual coaching, DATING COACHING, business programs, seminars, Internet courses and ebooks around emotional intelligence for your personal and professional enhancement. Top-rated coach certification program - fast, affordable, effective, no-residency. Email for information and for free ezine.