Dear Rosie & Sherry,

I enjoy your articles and am now seeking your advise in regard to my dating situation:

I have been dating a man for about five months. He is 35, comes from a good family, is a professional, employed with a good company, stable and attractive. We have similar interests and a similar lifestyle.

So what could be wrong?

I am confused about his actions. Whenever we go out to a movie, dinner, or ice cream, we always go Dutch. He has only offered to pay for me on our first date and my birthday. I was not given a gift or a card. I have paid for him on numerous occasions hoping that he would reciprocate the next time -- only to be disappointed.

Over time, I have observed that he is extremely frugal. I have mentioned to him that I am still into chivalry. I have gone as far as saying that it would be a kind gesture for him to buy me a rose, a drink, or offer to treat me to dinner once in a while. He agrees but never does.

Am I expecting too much and complaining for no reason? Or is his behavior an indication of something deeper then just being penny-wise?

Please give me your honest opinion.

Sally

Dear Sally,

You and this man need an honest, to-the-point discussion. Mentioning that you are "into chivalry" or would like an occasional kind gesture is not straightforward enough. You have to let him know that there's something important you want to discuss. We suggest that you find an appropriate time and place, and get to the point. Tell him that while you enjoy dating him, the two of you have very different perspectives on who should pay for your dates, and you are upset and puzzled about this situation.

You are used to having a man pay for your dates, and you don't understand why he always goes Dutch or is not willing to reciprocate when you treat him. If you don't mind paying your way sometimes but also want him to treat you, tell him so outright, instead of hinting and hoping he will get the point. If you do mind, tell him as well.

It could be that this man really thinks the fairest way to date is for everyone to pay their own way and only treat each other on special occasions. It could be that his family never gave birthday gifts or cards and he doesn't think they are important, or it could be that your birthday fell out very early in your dating, and he didn't yet feel comfortable giving you a present. Or it could be that he has financial problems you don't know about. Or he could be very frugal when it comes to some things and generous when it comes to others. Or, he could just be plain ol' cheap.

Whatever the case, you need to know his point of view. This will help you determine how much of his behavior is a "preview of coming attractions," versus how much he may be willing to change after he understands your point of view. It's very common for a man and a woman who are dating seriously to have different economic styles, and these can become a source of tremendous marital conflict if it's not worked out beforehand. So it's important for you to understand each other's perspectives at this point, and to see how willing and able each of you is to address them in a way that is comfortable for you both.

We think you can also get a little more insight into your friend's character by observing how he interacts with other people when you are on a date. There are fine distinctions between being "frugal" and "stingy." When tipping, is he fair, or is he stingy? How does he treat waiters, taxi drivers and other people who provide services? Nicely or with disdain? Is he "penny wise and pound foolish"? Does he give tzedakah (charity)? Is he generous in other ways that are not financial -- e.g. with his time, help, or compliments?

By better understanding his attitudes toward finances, you can hopefully work out an arrangement that's comfortable for you both. Good luck.

Rosie & Sherry