Dating After 50: New Thoughts about Who Pays

Whatever dating in the past was, dating in the present is different. You're different, your partner is different, and you both need to discuss, from the beginning, your expectations about money — at least for the near future. That arrangement may change as the relationship gets more stable and more desirable, but in the beginning, who pays is an awkward but necessary discussion.

Think about some of the reasons people do or don't want to pay, and examine your own money philosophy and practices in light of what benefits paying your way and paying someone else's way creates.

Reasons men may want to pay

There are several reasons a man might want to pay for the date:

  • It pleases many women. Some women like generosity and like the feeling of being taken care of. If you have the ability to treat dates to dinners or experiences that they enjoy or may not otherwise afford, you get a lot of positive reactions.

  • It's a tradition that many women expect. A lot of women over 50 expect the man to pay. This is the way they were raised or what they experienced in prior relationships. They may or may not offer to pay their way for something like an expensive dinner or a trip somewhere, but if you don't pick up the coffee tab or the movie ticket, they'll think that you're cheap.

  • It makes it easier to call the shots. If you want to do something that costs a lot of money, you don't have to confer as much or change what you want to do because your date can't afford it. Though paying for things shouldn't transfer all power to the person who pays (people don't like to think they're being bought), it definitely gives the payer an advantage over decision making.

Reasons men may not want to pay

Some reasons a man might not want to pay:

  • Women may want to contribute. By this time many women have been on their own, and they like the idea of carrying their own weight. They may think it's nice that the man buys the coffees or dinners part of the time, but they don't want to feel obligated by too many dinners, especially too many expensive ones.

  • They don't want to feel like a woman is attracted primarily to their money. Some men get downright aggravated about the idea that they're always expected to bear the expenses of dating. They reason that women want other kinds of liberation — equal pay, equal clout in decision making, and help with chores — so why shouldn't they chip in on equal financial responsibility?

    Some men feel that the primary motive of some women they've dated was financial help. Whether or not that was true, it soured their feelings for women, and sometimes, dating in general.

  • They can't afford it. Not every man can afford paying for dates every week. A boutique cup of coffee these days costs $4 or $5 in many parts of the country, and a man who is going out with several people could find himself spending $20 or $30 a week just on coffees, much less dinner and a movie. At some point, these men wonder why they always have to pay for an introductory meeting that benefits both parties.

    Though coffee dates are traditional, there are other enjoyable ways to meet people that don't cost anything: walk your dogs, go on a free gallery walk night, or attend a free concert in the park. (For more ideas of what to do on your dates, turn to Chapter 9.)

Reasons women may want to pay

Similarly, there are several reasons a woman might want to pay for the date:

  • They don't want to feel obligated. Do many men feel entitled to more decision making, even more sex, when they take a woman out to a fancy dinner? Yes, says the research on the subject. As a result, many women, having experience with this kind of reaction, insist on paying at least their half of the bill, just to make sure that they don't incur any emotional or sexual debts.

  • They want to reassure the guy that this isn't about money. Some women, especially women with jobs or means of their own, are sympathetic to men's burden of always having to pay. They don't mind paying their own way, and they know that some men are suspicious of women's motives if they always defer the check to the guy.

    They'd rather pay their half or occasionally treat their date than have him think that dating has anything to do with getting freebies.

  • They're used to paying their own way, and they want their date to know that. Some women have shared financial responsibility their whole life, even with their husband or other committed partner. They've kept everything separate — it's just the way they do things — and they don't feel a need to do anything different now.

Reasons women may not want to pay

And here are some reasons a woman might have for not wanting to pay for a date:

  • At least in the beginning of a relationship, it may offend their date. Some men are a bit put off or at least uncomfortable if a woman insists on paying her way on the first coffee or even the first date. They may see it as overly aggressive or controlling, or even an indication that the woman doesn't want a second date.

    Women are unsure of what a man's reaction will be, so on a first or second meeting, they may not even offer to pay and just say thank-you, hoping that this is honoring a man's traditional role.

  • They're looking for someone who wants to pay for things. Some women are very clear that they want someone who will support them or at least do the financial heavy lifting in the relationship. They don't want to split bills, and they resent a man who asks them to. They wouldn't want to set the wrong precedent by offering to split anything.

    This can be particularly true for women who had to support someone in the past and don't want to replicate that situation.

  • They can't afford it. Some women have to watch their pennies very carefully, and they can't afford $10 just for coffee every first meeting. Women who are helping support adult children or grandchildren, who don't make a lot of money, or who are on a minimal fixed income welcome a man who likes to take a woman out or expects to pay for the bill on the initial meetings.

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