By Dave Singleton
Courtesy of Match.com's Happen magazineWhat did I learn after recently querying gays and lesbians on the age-old question, “Who pays for the date?” The road to dating hell can be paved with good intentions. Christina and Andrea, a blissfully happy year-old couple, agree on many things in their relationship. Who pays for the first date, however, is not one of them.
“I insist on going Dutch,” says Christina. “I’m very independent and would not want to give any power to the person on a first date. In other words, I would not want to be beholden to anyone from the outset.” Andrea, on the other hand, says she would pay for the first date with hope that, if there were a next time, her date would pay. Both of these women have the best of intentions and are equally generous and classy. They just approach dating in a different way.
Traditional heterosexual dating rules dictate that men always pay and women demur when the check arrives. But times change. Despite the fact that many straights are sticking by traditional roles, backed by books like
The Rules, many more have broken out of the mold and approach dating as equals. After all, there’s more economic equality, less focus on stereotypic sex roles, and plenty of consciousness surrounding the use of money as a power play.

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As for gays and lesbians, we haven’t had rules for dating, period. Only now, 35 years after Stonewall, do we have enough “out” clarity to develop norms and standards. One of the joys of being gay is the chance to avoid outdated rules and make new ones. So the issue of who pays on a gay and lesbian date seems like a no-brainer, right?
Apparently, it isn’t that easy. There’s no consensus, and money is always a powerful issue. Here are my guidelines for how to evaluate dating and money issues, as well as handle the first and (if you’re both lucky) subsequent dates.
Stay aware of the real issues. Psychologists claim that money concerns are often about boundaries and power. When we discuss where we live, what we do, and what we own, aren’t we economically “name dropping?” Your date will be either attracted or repulsed by such blatant economics as you get acquainted, so make sure you consider these questions in advance:
Do you or your date offer to pay as a power play?
If you insist on paying on the first date, are you setting yourself up as a “Sugar Daddy” for a younger man who might expect a free meal and all-expense-paid evening as a perk of being young, cute and gay?
If you don’t make an attempt to pay, will you look cheap?
If you agree to go Dutch, will you come off more as buddies?
At least, if you are clear about the potential issues, you’ll make more informed decisions that will (hopefully) reflect how you want to come across to your date. Also, establish ground rules upfront before you ask or are asked out. Confusion about who pays can lead to dating disaster during an otherwise great night. Again, grace goes a long way to showing who you are as a person. Your intention counts. If you are trying to make your date feel flattered because you want to pay, then make sure that comes across. Go light on the insistence. You don’t know how your date will take it.
Consider inexpensive pre-screener dates. Mitigate the chance of having a horrible evening by scheduling a coffee date wherein there’s minimal obligation as you get a sense of each other. With pre-screener dates, you should go Dutch. It should be a very inexpensive scenario, so there’s no need to worry about who pays.

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Manage the oh-so-important first date. “Dutch is for friends,” says Leslie. “The asker should pay, and be clear about it.” But if feel that way, make sure that you plan a casual, less-expensive date for the first time out than going to an expensive dinner.
“I hate it when someone offers to go Dutch, I think that "settling up" at the end of each date suggests that there won't be another,” says Kevin. So, if you asked your date out, are having a good time and want to see him again, you could offer to pay, and see if he offers to pick up the next one. On a first date, it’s a charming and seamless way to get to the “second date” question. If he insists on paying, however, it might be an indication that he isn’t interested. In this case, go Dutch, follow his lead, and don’t be insistent on paying.
And if you decide during the date that you don’t want to see the person again, then it’s probably best to split the bill -- unless you have agreed ahead of time to pay.
Share the cost of subsequent dates. Too much discussion of finances is a dating buzz kill. But if you and your date both have intentions to share, you’ll come up with creative solutions. Many newly formed couples agree to alternate paying rather than going Dutch. Usually, it all evens out in the end.
Divide and conquer on multi-plan dates. Are you planning dinner and a show? The smart thing to do is for one of you to pay for dinner and the other to pay for the show. In general, splitting the evening’s bill along these lines allows for graciousness and equality, which is an unbeatable combination. Hopefully, dinner and a show doesn’t mean burritos at Taco Bell followed by $300 seats at the Madonna concert.
And remember this one rule above all others: When you are dealing with a touchy subject like money that doesn’t have clear cut right and wrong responses, you want to come across as generous and fair but sensitive, too.
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