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Dating Advice #68 -
Dating Advice 68

Dating Advice #68 - "El Cheapo?"

She's looking for generosity, but he's not financially forthcoming. How does she deal with these dynamics?


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.


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

December 28, 2002

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Visitor Comments: 11

(11) Anonymous, April 19, 2005 12:00 AM

know the feeling.....

I've been dating someone for 7 months that is extremely frugal. He rarely treats me to anything, and if he takes me to dinner or lunch, we often "split" something. Sometimes I want a whole plate! haha! He also can go buy himself a new sports watch, ipod, or treat himself to Vail with the buddies and leave me at home. He also said he would never take me on a trip unless I paid my own way. Our relationship will eventually come to an end, but the moral to this story is - IF HE IS SELFISH WITH HIS MONEY, HE WILL BE SELFISH WITH HIS HEART!

(10) Anonymous, January 2, 2004 12:00 AM

looking for a mother

if u stay with him i believe u will be supporting him. it will start as passive aggesive, i bet he goes to bed with a cold.he's looking for a strong woman to support him when he's sure he has u. he'll look to other women still holding on to u.before long he'll start making u think it's your fault he strayed now your esteem is in peril.he won't leave but he won't respect u either,he'll use u to other women as why he won't commit but he's not committed to u either, he has no more respect for them than he has for u and he won't chg how close am i,he's probably spending his money on the ones that won't pay stop paying ,he'll leave.

(9) Anonymous, November 11, 2001 12:00 AM

This man is not interested.

He may be waiting for this woman to wise up and not continue seeing him. This way he does not have to face his responsibility in breaking it off and will keep leading her on until she realizes that this man is not interested in marrying her, much less dating her.

(8) Anonymous, July 5, 2001 12:00 AM

He may not be too interested in her.

This woman doesn't expect the man to always pay, so it can't be said that she is after his money.

I once dated a man who either paid only for himself or thanked me when I paid, but would never treat me. It wasn't until after we broke up that I found out that he just wasn't that interested in me. How did I know this? (1) He wasn't terribly upset when I suggested that we break up, and (2) I heard of him complaining about how his new girl-friend didn't seem too interested in him, even though he was spending lots of money on dates and gifts for her!

(7) Anonymous, June 28, 2001 12:00 AM

Long term

I found you missed one point in the letter. They are into a 5 month relationship and at that point why is it the male that should always pay. You call it "dutch" as opposed to "sharing". I do agree that he should show a little more by buying a gift, or even dinner on occasion. But the entire dating should not fall onto the males shoulders.

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