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Part 2: Equal Pay? 10 Dating Conundrums in the Era of Gender Parity

June 19, 2015 Barbara Ballinger & Margaret Crane

Most of us encounter a host of thorny issues when we date at any age, but particularly after 50—who pays for a meal when we both have funds, how much to spend on a gift, ever to go Dutch? We’re certainly not etiquette gurus, but we learned when we became single, and listened to others debate these do’s and don’ts, that there are no clear-cut answers. Consider our advice as a guide, not a rule book. Nothing’s etched in stone, especially in today’s fast-changing dating world.

Question: Should men and women discuss cost sharing before a date? 

Answer: It’s certainly a way to remove the mystery from the ending of a date and that sometimes awkward moment when the waiter presents the bill. There may even be a moment of silence before you or he pulls out your credit card or cash. But such a discussion in advance can be a sure-fire way to make what might be a future romantic relationship seem more like a business transaction. And if he suggests you split, what does that do to your lust-o-meter, especially if he’s ordered two glasses of an expensive wine and you’ve ordered the house brand or a Perrier with lime? Do you split evenly? Go with the flow, which means trust your gut. If you’re not interested or there’s no chemistry, speak up and suggest he pay for his portion and you’ll pay for yours. This is really easy to do when you know you have no intention of seeing him again. If you do think the relationship might have legs or at least be worth another date, suggest, “Why don’t you pay for tonight and I’ll get the next one?” At least, always carry at least one credit card and cash just in case you don’t want to be indebted.

Q: But what generally are the rules about the first date?

A: Most think it depends on how old fashioned you or the guy is, and who asked whom out. Both of us felt the guy should pay, and most men that both of us met and are now dating felt the same. Barbara knew she generally wouldn’t be interested in someone who expected her to pay for that first meal or drink. Margaret agrees. A high-school guy friend picked up the first bill, and two years later still usually pays. When the tab came on their first date, she wasn’t sure what would transpire but he said, “This was fun. I’d like to do it again.” That has been the case with Barbara’s current beau whom she was fixed up with 2 1/2 years ago. He chose the restaurant, picked her up at their mutual friends’ home, drove, and picked up the tab for a three-course meal with wine.

A couple Margaret met in her grief-support group reflects a slightly different scenario. On Joan and Mike’s first date, they went to an Olive Garden for a modestly priced meal. When the bill came, she was uncomfortable about who should pay. She recalls, “The waiter gave the bill straight to Mike, and I was adamant that he would not pay. Although he said he would really like to pay, he allowed me to put down my credit card also. I was headstrong that he would not pay for me.” So, do what feels instinctively right but when in doubt, expect him to pay, or split.

Q: Who pays for the second date? 

A: It depends since some women who’ve been treated to dinner want to level the playing field the second date and pay, but both of us decided the person who pays should be the one who initiated the date or chose the restaurant or event. Two days after Margaret’s first date with her high school friend, he called and asked her to go to dinner at an upscale restaurant. Again, he quickly reached for the bill. She was OK with this because he had asked her, and the restaurant was his choice. For Barbara, it was somewhat similar, though the second meal was far less upscale—a well-known pizza restaurant in Boston where the guy, whom she’s dubbed Fix-up, lives. He had invited along his son and fiancé, a bit unusual but Barbara thought it would be fun since she loves being around her thirtysomething kids and their friends. He paid for everyone since the date idea was his and to eliminate any awkwardness in front of his family. When each of us invited our new guy friends to our homes for a first home-cooked meal, we bought the groceries, though we each said “yes” without skipping a beat to the guys’ offers to bring wine.

Q: What about that third date or more dates as the relationship progresses? 

A: Again, it depends on the personality of the guy, the way in which he was brought up, and what our gut dictated. In our cases, initially the current beaux wanted to pay for most dinners. We each began paying for some lunches. And now past the second year of dating, what we do depends on our mood and the circumstances. Margaret has paid for a few dinners. On her third date, they went to an event in a park and stopped for a bite to eat afterward. This time she insisted on paying. He seemed surprised, actually a bit taken aback, but understood this was important to her. She didn’t want him to feel he had to “take care” of her or that she was taking advantage of his generosity. Now two years later, he still pays for most dinners, but she reciprocates by inviting him to her home for dinner and will often pick up a brunch or lunch tab. Or he gets included with her family and her mother always pays. Sometimes, if he protests, Margaret will give in and let him take the check. Barbara’s situation is similar—her guy friend usually pays for dinners, buys wine almost always, and many groceries when he visits since they spend more time on weekends at her home. They’ve worked out a routine that she has found comes naturally without discussion. At one point, they chatted about keeping track of costs and decided it would sour the romance.

Barbara remembers following the same pattern with most guys who made it past the second or third date. Many found the concept of a woman offering to pay endearing; some were even surprised since they said few women ever offered to pay. One former date told her he resented that another woman he was dating never offered to pay. (Yes, two cupcakes under consideration but that’s another post.) He said something to the effect, “She always had her hand in my pocket,” but he explained further that her income was paltry and felt it was the only thing to do.

Some couples discuss finances openly and often. As Joan and Mike continued to date, they talked about who would pay for their trips and gas. He still, however, picks up most dinner tabs. “On our bigger trips (Oregon and the Smokies), we decided to split the cost. On our small trips like weekends away it varies who pays for the hotel (often found on Priceline),” she says.

And though who pays for one meal or two typically won’t undo a relationship, a pattern can. With one of Barbara’s former dates, she saw him become less generous over time, even though he frequently bragged about his former big jobs, drove a foreign car, and more galling—always seemed to have to be right. He stopped paying for movie tickets and conveniently disappeared at the time of purchase; he kept his hand in his pocket when they hit a grocery store before going to her friends’ home one holiday weekend, yet, said he loved fresh shrimp and wanted to get a pound (translation: She would be paying for the fish). When he double dipped into the cocktail sauce at her friends’ home, never suggested treating their hosts to an inexpensive dinner after enjoying their hospitality, and told Barbara they needed to split a bill for dinner on the way back to her house, she knew this relationship was over. The final straw: He asked to take home the brownies she had received as a gift. This wasn’t all about the money, but his lack of a generous spirit.

Q: When is it proper to go Dutch or split the bill?

A: Any time, you feel you don’t want the guy to have an expectation that there will be another date or if you sense they’re not feeling generous or interested, or you have zero interest. Margaret never goes Dutch with her beau unless it’s buying a gift together for someone or shopping for groceries for a dinner they’re preparing together for themselves or friends. When it comes to tickets, if it’s his suggestion, he pays; her suggestion, she pays. Barbara has almost never split the bill in any dating, except one time when she felt uncomfortable since she wasn’t sure she wanted to see the guy again. He reached for the bill on a first date for dinner; she suggested they split it. He acquiesced.

For a few of Joan and Mike’s initial dates, they put in both credit cards.  He said he was uncomfortable with that, so she agreed they could switch off and take turns paying. “We did that for about six months. Now he mostly pays for dinners out; I mostly pay for groceries. Although we trade off on, we don’t have a set system.”

Q: What about gifts and trips?

A: A couple usually establishes a pattern that works for them in these matters, too. And the good news is that if the relationship has legs the first gift or trip won’t be the last, so differences can be made up if important to either person.

The first year of dating, Margaret’s honey asked how much she thought they should spend on their first holiday gifts for each other—eight months after they started dating. He suggested a figure that gave Margaret palpitations. She felt it was too high. She countered. And that’s what she spent; he spent three times more on her, and she was suitably embarrassed and said so. At least she knew the name of his favorite men’s shop and bought an item of clothing there. Their first trip together reflected one of payment negotiation. Since the two went to New York to hear her son perform, Margaret paid for her airline ticket and half of the hotel room and expenses. On the next trip to Houston to meet his family, he picked up the tab for all except air fare. Margaret used airline points.

Barbara likes to give little gifts for no reason, especially colorful patterned socks, which most guys who have made it past date five or so have received. She and her current squeeze don’t give lavish gifts, and he explained he doesn’t feel comfortable finding the right item. “I’m not a mind reader about what you like, so share,” he explained. She presented him with a list of her favorite stores where the sales staff and owners know her taste.

Barbara also explained that in her family nice cards are de rigueur even more than gifts…especially those Papyrus ones with a seal that can cost upwards of $5 or so. (Buy three, and at least you get the fourth free.) The tradition started because one family member often used cards at hand, which sometimes meant crossing out “Merry Christmas” and writing “Happy Birthday.”

Q: Any difference if the couple is gay? 

A: Steph T., a transgender, says if she goes out with a man, he always pays and then often expects something after that…hmm. Angela A., a T.V. producer, said whoever does the asking out should pay. “If I meet a woman online, we split the check. Often times we’ll discuss who pays in advance when deciding on where to go.” Angela tends to pay because she can afford to do so and likes to go to nice places. She’d rather not compromise and go to some dive. “As a relationship progresses,” she says, “it’s usually split. That person will pay one time, I’ll pay the next. However, no one keeps score. That’s the fastest way to ruin the beginning of a good thing.”

Q: Should a bigger income make any difference, which might be obvious because of inequality in professions, homes or inherited funds?

A: We think the best tactic is to follow the pattern of whoever initiates an idea whether tickets, dinner, or a museum visit is the one who pays. If eating out is unaffordable or tickets too expensive, don’t eat out or buy expensive concert, theater or ballet tickets. Or focus on dinners at home, stream new movies, or watch old ones on cable or Netflix.

Q: What about gifts for each other’s family members or close friends if you get to that point? 

A: This depends on how well you know them and what you feel, if emotionally connected. Unless you’re in a committed relationship, and even then, err on the side of doing less than more. It removes the pressure. Again, a nice card or note is always appreciated. Barbara has purchased some gifts for her beau’s children and one grandchild; and he has done the same for hers, but it’s all about what each wants to do rather than strict rules. And when they go to friends’ homes for dinner or visits, he always brings along wine and takes out the couple for dinner if staying with them; she often bakes or brings along a gift.

When Margaret visited her beau’s family in Houston, she sent thank-you gifts for one lunch hosted by his sister and another hosted by his niece. These were small purchases. And in the end, they’ve both tried to stop ruminating about what’s right or wrong; they make a decision and stick with it.

Q: Cultural challenges; what to do when you know the way he was raised lurks in his brain?

A: Ethic and age differences, different regions of this country or abroad, family traditions may show up in how money is handled. Some men from different religions backgrounds also believe they must pay for everything to be the good providers they’re expected to be. Be a detective, watch, and listen to pick up clues, and then make your decision whether you ask to contribute or split any costs.

Bottom line: Money and dating often represent a delicate balancing act, but most couples find bringing out a calculator and tracking each dollar spent will get in the way of getting to know the other person. Rarely, for us, has money been the sole reason a relationship has or would crater. If resentment starts to build, find a time to discuss your concerns calmly. Tell your date how you feel over wine or drinks rather than during a meltdown and come up with a solution. Let him buy the first round; you cover the second.

For more information about this topic, a study, “Research on Which Gender Pays for a Date Shows Changing — but Also Resistance to Changing — Conventional Gender Norms” by David Frederick, co-author and a professor at Chapman University, provides interesting reading.




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