Dear Dr. Alasko: After my fifteen year marriage ended in divorce a year ago, I've been on a few dates with J., who I really like. He's new to the area and is setting up a professional office. But he seems to have some financial complications and gets irritated whenever money comes into the picture. Even paying for dinner can be stressful. I'm financially secure and worry about getting involved in a difficult situation. How should I proceed?
Dear Reader: Very carefully. Here's the most useful rule you can apply to your situation, one especially necessary when dating a new person: everything counts.
Which means that everything your new date or friend says or doesn't say, does or doesn't do, has a meaning that points to something in the person's character, personality and -especially - their history. Your job is to figure out the meaning of each and determine how important it is to you.
I'm not saying you need to observe and interpret so that you can criticize or judge. Just that you need to learn the facts and decide how you want to proceed. You especially need to know if the issue is a deal-breaker or a relatively minor habit that J. might be able to change.
This situation is surprisingly common when two more mature people begin a new relationship. There's often an inequality of income and this can be a source of stress. The central question is how much stress it may produce.
There are two basic issues involved in your situation. The first is J's apparent unwillingness to talk openly about his financial situation. We are all sensitive about money because it's connected to our sense of accomplishment. Men are even more sensitive because accomplishment and a sense of masculinity are exquisitely interwoven. So one of the questions you'll want to explore is whether his reluctance to confide concerning his finances is whether that has to do exclusively with money, or whether he's got larger issues involving his masculine self-image overall.
The other issue is about J is capable of being forthright and candid. When he's exhibiting signs of stress around a dinner check yet refuses to talk about them, he's not being candid with you about what's going on with him. Naturally you're not expecting him to give you a complete financial statement revealing his income and possible indebtedness at this early stage of the relationship - but you certainly are right to be concerned about his financial viability.
I suggest you wait for a few weeks and see how things are going between you. If you find that you and J. continue to enjoy each other, and there are not other serious issues, then simply ask him for a few minutes' time, sit down together, and ask him to clarify his financial situation.
This encounter would require a lot of skill on your part, but I can assure you that everyone wants the same thing: we all detest criticism and judgment but desire to be understood and accepted and. Men, above all, are terrified of being humiliated. So if J. has had financial problems in his past, he might be rightfully afraid of openly discussing his current situation - which is bound, in his eyes, to constitute a failure. That makes him very vulnerable, and men instinctively avoid being vulnerable.
However, you cannot allow an unspoken issue as important as finances remain under the table for too long without openly exploring the details. To repeat, your goal is to learn the facts and develop understanding, and then decide whether you can tolerate the situation with acceptance.