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Dating Advice #91 - The Sneakers and Bag-Lunch Date
Dating Advice 91

Dating Advice #91 - The Sneakers and Bag-Lunch Date

He's terminally cheap. Could that have anything to do with his lack of success in dating?


Dear Rosie & Sherry,

I have a few questions:

1) Why do women approach dating as some kind of fairy tale? I suggest that it would be a lot more comfortable if we didn't get dressed up, and just wear work clothes (which for me includes sneakers). I can understand that at a wedding a woman might want to wear high heels, but why pain yourself for a date? It's not like I'm going to say to myself, "Wow, she wears high heels so well, I'd better marry her."

2) Why do women want to go out? Why can't we just stay in the house and talk? (Either her house or mine. I can even cook if she'd like.) Why do we need a restaurant to talk? Does the expense of the food make a better date? Why do we need to go to some amusement park? If I want to get motion sickness I can go for a ride in a yellow cab. Before you start calling me "cheap," let me just say I hate spending money on unneeded things. Spending a lot of money on 2 ounces of meat is a waste.

3) Why can't women order the cheapest thing on the menu? I do. Is there an unwritten law saying you can't get the cheapest thing on the menu? If I'm paying, shouldn't she ask before ordering those expensive dishes?

4) Why am I paying for her food? When and if we marry, fine, then it's "one for all and all for one." But for now, we have no commitment to each other. So why isn't she paying for her food, cab fare, etc.? I understand that in the "old days," women didn't have money or power, and men were "required" to "protect" them. But this is a new time -- women have money and power, and can take care of themselves.

When I discuss this with my friends, I don't understand the response. They think I'm nuts, and I should just "go along" so I can marry some sweet woman. I'd like to add that I enjoy your articles and (mostly) agree with your advice. Thanks for your time.


Dear David,

We're glad you wrote to us. Frankly, if your questions are a reflection of the attitude you display when dating, you're going to need a little help in order to develop a successful courtship with a woman.

The fact that you are, as you describe it, "cheap," can and will handicap you a great deal in the social arena, unless you accept certain realities of life. Life isn't always based on common sense and frugality. Even though you have a strong tendency in this direction, if you want to be able to meet suitable dating partners and develop a healthy relationship with your spouse, you'll have to accept certain social conventions.

Let's look at the issue of dressing for a date. Many people like to dress nicely because it makes them feel better about themselves. When a woman dresses up for a date, she wants to feel pretty and special, and she wants to make a good impression on the guy she's with. So she will wear fashionable clothes that she thinks flatter her, fix her hair, and put on makeup. She could certainly feel more comfortable in sneakers, but they won't make her feel special. She may also think that unless she dresses with care, her date will be turned off because he will think she doesn't care about making a good impression.

By the way, if you show up for a date looking as though you didn't make an effort to look neat and nicely groomed, you won't make a good impression, either. At best, your date may think that you don't have any idea how to be presentable (or even that you're a slob). At worst, she'll think you don't care enough about her to want to make a good impression. Really casual clothes have their place -- hikes, sports activities, etc., but for other dates most women (and guys, too) prefer to dress nicely, even if it's "dressy casual."

The next question you asked is about going out versus staying in. You may be a "homebody" whose greatest joy is relaxing comfortably in your own living room. There's certainly much to be said for quiet evenings at home, but these shouldn't take place during the early phases of courtship. We'll give you just a few reasons why this is so. Practically speaking, most women would not feel comfortable entertaining someone they are just getting to know in their own home, and they won't feel comfortable being entertained in his home, either. They certainly won't feel "special" if they are expected to cook or prepare a meal, or to simply help him clear his dining room table.

In addition, having to be a host or hostess detracts from the business of the date. You should rather be concentrating on getting to know each other. Most people find this easier to do at a location outside the home.

Even though you may not realize it, there's a lot to be said about ambiance. When a man chooses pleasant surroundings as the background for a date, a woman feels that he thinks the evening has importance. The location of the date doesn't have to be expensive. A walk though a botanical garden, an afternoon at a museum, a cocktail at an attractive lounge in a hotel lobby, all show a woman that you gave the date some forethought so you could spend time with her in a pleasant atmosphere. Interactive or sports activities (biking, tennis, or even a hike) also have a certain appeal that enhance the mood of a date.

Finally, don't think that being married will let you off the hook when it comes to getting out of the house. Most women like a change in routine and look forward to going out for dinner, a concert, a cup of coffee and dessert, or even an afternoon in a museum. When their husband goes out with them, they feel that he's proud of them as a couple, that he knows she likes a change of routine every once in a while, and that he doesn't take her for granted.

So, we suggest that you bear this in mind even after you become involved in a courtship. If you treat the woman you’re dating (and later your wife) to an afternoon or evening out, you'll be doing a great deal to enhance the process. We recommend that all married couples go on a "date" once each week. And don't worry, when you're married you can get away with a lot of "cheap" dates interspersed with occasional fancier ones.

Now let's get to your question about ordering the cheapest thing on the menu. Because you think that it is foolish to eat in a restaurant, you don't enjoy the experience and try to make it as painless as possible by ordering the cheapest thing. Very few people (men or women) think this way. They look at eating out as a pleasant experience, an opportunity to enjoy a meal that they may not have the time, energy or know-how to prepare for themselves. People who work hard and feel harried often see eating out as a chance to relax and have someone else do all the work.

That doesn't mean they have to order the most expensive thing on the menu. Most people don't. If they are being treated, they are usually considerate enough to order something medium-priced. However, if you are escorting a woman on a date and take her to a restaurant, it is natural for her to assume that you would like her to choose something she'd like, and that you don't have a problem footing the bill.

Even though you may not feel comfortable pampering yourself, try to take some pleasure in the fact that your date probably enjoys the pampering. When you develop a relationship and are married, you'll want to make the woman in your life happy, and taking her out to eat is one way to do this.

Actually, one of us (we won't tell you which one) is also "cheap." We understand how silly and wasteful it seems to pay a lot of money for a restaurant meal that can be made more cheaply at home, or to wear dressy clothes when something less stylish is more comfortable and less expensive, or to pay for a movie when a video rental costs a lot less. Yet the one of us who is cheap still appreciates going out on occasion to a restaurant, a concert, or to lunch with her girlfriends -- and doesn't even order the cheapest item on the menu!

Since we're talking about cost, let's look at the issue of who pays for a date. We think it's logical that the person who initiates the date (who asks the other person out) should pay the expenses. That is the prevailing expectation in American society. It doesn't matter what the incomes of the couple may be, or the fact that it seems logical for each of them to pay their own way. This is the expectation in our culture, and it hasn't changed in the past 30 years, despite the influence of the women's movement.

Your friends are right when they tell you that you have to go with the flow on this. If you don't pay for the date, or resent the fact that you're expected to pay, or if you are stingy, the woman you are with will probably never accept your invitation for a second date.

We think you will have a much easier time dating if you look at courtship as an opportunity to make a woman feel pretty and special, at the same time that you try to get to know her. (This applies as well when you take you wife out once you are married, and even when you occasionally buy her a gift that makes her happy even though the item may seem senseless to you.) We know it gets frustrating to date and date and spend and spend, especially when it takes a while for you to find a woman with whom you'd like to develop a relationship. However, going out on dates is part of the courtship ritual, and going out costs money. You'll simply have to accept this.

When you change your attitude, not only will you be less resentful about the cost and effort of dating, but you can learn to enjoy the atmosphere, the entertainment, and the chance to treat yourself. You'll also find that a different attitude will make you a much more appealing dating partner.

We hope this has been helpful, and wish you the best of success,

Rosie & Sherry

January 19, 2003

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Visitor Comments: 19

(18) Anonymous, July 26, 2008 9:50 AM

All right, men. Here''s the deal. Women have been held up on a pedastal for a long time because we are the ones who go through the pain of having the children. We''re the ones who go through PMS. And we''re the ones who usually pick up after everyone, help raise the kids, cook, clean, and deal with the family''s melodramas after marriage. So yes, women should be treated with respect, I believe simply for the fact that we have it harder than men. My father even strongly condones this, has been married to my mother for about 40 years, and thinks that today''s men who don''t pay for dates don''t respect women, are whiny wussies, and are con men at best. And yes, women want to feel special on a date. So take her out. You may meet the woman of your dreams this way, and manage to not get her angry.

Andrew, December 11, 2012 4:38 PM

Women have it harder than men? Really

(17) Anonymous, June 17, 2002 12:00 AM

I still don't get it

While your responses to David with respect to dressing up and going out for dates are cogent, your stab at explaining why women never pick up the tab on a first date (or even pitch in) just doesn't hold. Any way we look at it - women's position in society today is vastly different than it was in the past - why should this vestige be an exception?
You assert that the party initiating the date should foot the bill. At the least, that's disingenuous. We guys are expected to initiate (i.e. make the call), again by virtue of some outdated notion; does that in any way indicate that we're more interested in the date than the woman is? That's facetious. It just manifests the old societal roles of men as the active pursuers and women as chaste and uninterested. Now - how close to the mark is that?
Moreover, your explanation doesn't hold in and of itself. Women have asked me out more than a few times. Did those women, who by your standards should have been expected to pay, ever actually pay? I'll help you out here - none did. Why? (O.k., in the course of my dating experiences there have admittedly been a few perfunctory offers of women to shoulder their half on a first date - but I know half-heartedness when I see it).
Moreover - is it too much to expect to be thanked for taking a woman out and paying for her dinner? I can't count the number of times I haven't merited to have the words "thanks for dinner" thrown my way.
As you probably can tell - guys like David and I carry a litany of grievances on account
of our experiences with modern dating etiquette, which many guys feel offer men a raw deal.

(16) Anonymous, May 30, 2002 12:00 AM

Women's approach to dating is self-centered

Why is it that everything you have suggested about the date is centered on the Woman's comfort? Don't men have any rights on dates as well?

(15) sonia, February 22, 2002 12:00 AM

are you prejudiced?

Some people think you're better because you do not give importance on money. It is a strong prejudice, and I know about it a lot- I had to grow out of it. I used to have little luck in dating. Would never make up or wear anything but jeans and slippers. Well, the fellow was supposed to love me, not my dresses! And it gave me a huge surprise once a boyfriend told me, "Honey, I may be a rough guy, but I want you to be my queen ,to look like a queen!" So I learnt that lesson, people like to be treated as special. It is still difficult for me. I finally married another man, who also likes to see me dressed up and in makeup. He takes it as a sign of love to him.

So think about it, you're pleasing the girl, you're making her feel important. And going out is not wrong either. Just have fun!

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