Yes, it’s not just looks, values, charm and that elusive quality known as chemistry that matter when you’re an older dater. Whether you’re looking for something casual or hoping for a lasting love connection, money plays a role too. And it can be a minefield. When you’re meeting for that first coffee date, there’s no way to know how close that stranger is to a financial precipice and what that might mean for a future relationship.

“A lot of men have been divorced, may still be supporting adult children, and they are less financially secure than they ever imagined they would be at 50 or 60 or 70,” notes Leslie Bennetts, author of The Feminine Mistake: Are We Giving Up Too Much? Many men are looking for a soft place to land—but then, so are women. What this has bred on both sides of the gender divide, says Bennetts, “is a lot of suspicion and mistrust because the old rules no longer apply and nobody knows how to act.”

“So many of the problems I have in dating revolve around money,” says Mark, a 74-year-old divorced physician in Florida who asked that his last name be withheld to protect his privacy. “Either women make it clear before they even meet me that they are looking for financial security, or I meet very wealthy women who intimidate me, and I worry I can’t keep up.”

You may not be able to avoid every pitfall of dating at this stage of life, but here are a few suggestions for sidestepping money problems.

With the question of who pays fuzzier than ever, you need to set the rules before there are any awkward silences. If you prefer to pay, etiquette expert and AARP Modern Manners columnist Lizzie Post suggests saying something like: “I’d love to meet up for a cup of coffee. Please let it be my treat, regardless of how this works out.” Prefer to share the cost? You can say something like: “My usual practice on first dates is to split the bill. Does that work for you?” Of course, if you still hew to the old rules of courtship, you could gently state that at the onset. “We’re all still living in the patriarchy,” says Lisa Zaslow, 62. “The least the guys could do is pay for the first date.” But be prepared for pushback.

Costs can pile up quickly. Single Gen Xers spend an average of $172 per date, while boomers shell out an average of $127 when they meet up, according to the BMO Real Financial Progress Index. To keep spending in check, create a dating fund, advises Lakshmi Rengarajan, a dating coach and creator of the Later Dater Today podcast for midlife daters. For instance, if you allot $200 a month for dates, you can have multiple low-cost coffee meetups or a couple of pricier nights out. The key is to honor your limit. “Once that money runs out, you’re not going on any more dates that month,” says Rengarajan.

For many of us, a splashy first or second date creates a sense of heightened, and perhaps uncomfortable, expectation. Judith, one of the writers of this article, was in her 50s when she was taken on a first date to a Broadway show and a swanky Manhattan steak house so her date could show her the plaque the restaurant had installed in his honor. “Then he wanted to show me the pied-à-terre he had just bought for his future mistress,” she says. “Unbeknownst to me, he was still married and was auditioning me for the role.”

At the other end of the spectrum, when Zanne Koehne, 48, of Louisville, Kentucky, began looking for a new relationship, she bought a zoo membership so she’d have a fun, inexpensive place to take her (hopefully animal-loving) dates. Bela Gandhi, a dating coach and founder of the Smart Dating Academy in Chicago, is a fan of such low-key outings. “I like easy dates,” she says. No zoo in your area? Think coffee shops, museums or bookstores.

Maybe you just don’t want to feel any obligation with someone who’s insisting on paying. Maybe things are going poorly and politely leaving cash is a better alternative than excusing yourself and trying to shimmy out the bathroom window. Whatever the case, you can just say, “I really appreciate that you want to treat me, but I’m not comfortable with that, so I’m going to leave $40 here,” says Post.

You know how much birding costs? How about community organizing or other volunteer events? There are endless cheap or no-cost activities that force you out of your home and into the company of like-minded people, says Ed Coambs, a financial planner and author of The Healthy Love & Money Way. Free and low-cost dating apps are another option, but keep in mind that just 3 percent of adults 50 and older were using online dating platforms or had used them within the previous year, according to a 2023 Pew Research Center study.

“I’m infamous among friends for a lifetime of attraction to sketchy guys,” says Andi Sporkin, a communications executive in Los Angeles. “Now as an aging boomer, I consider my ability to quickly recognize these qualities as one of my superpowers.”

Nearly half of online daters age 50 and older say they’ve encountered someone they thought was trying to scam them, according to the Pew Research Center. So make sure you verify whom you are actually talking to by searching their name online or doing a reverse Google image search with their photos; you might find out that the image is associated with another person or with reports of scams. Avoiding a video call or in-person meeting, or asking for money for any reason whatsoever, are bright red flags. Dating apps often alert users to recent scams, and aarp.org/fraud has info about romance scams and other types of fraud.

As is the case with physical or emotional intimacy, it’s best to do only what feels appropriate to you. If a question about your finances feels too personal, you can simply choose not to answer it. You can also turn the question around and politely ask why the other person wants to have that information. “People need to earn your story,” Gandhi says. “They don’t get it up front just for asking.”

On the other hand, don’t wait forever before questioning suspicious financial behavior. Recalling one of her relationships, actor and author Annabelle Gurwitch says, “We generally alternated paying for things, but after about a year, I began to wonder why he paid for everything in cash.” It turns out the boyfriend, who had been making a six-figure income for years, was in bankruptcy. “But he did have an extensive collection of $1,000 sneakers,” Gurwitch adds. When she asked her boyfriend how he planned to live once he retired, he coolly replied, “That’s what my children are for.” Some financial information from a partner you simply can’t unhear.

When Koehne started dating Tonya Calilung five years ago, Calilung wanted to split their checks—a request born out of past abusive relationships she’d had in which money was intertwined with issues of power and control. Koehne, too, had been in an abusive relationship. The women got married two years later—those inexpensive zoo dates really worked!—and today Zanne and Tonya Koehne are as enmeshed as any couple could be. They still don’t pool their money, however, and they take turns paying for nights out. “I think we both implicitly knew that in order to be comfortable, given our pasts, money had to be separate,” says Tonya, 53.

So when you’re first getting to know someone, don’t immediately label them as cheap or extravagant or anything in between. Learn a little about what has happened in their financial past. By this stage of life, almost everyone has a diverse mix of experiences that shape their money mindset and financial situation. “If you see a potential future with this person but respond with criticism, it can potentially discourage any future openness about their situation,” says Coambs. “Treat the information you receive with compassion and empathy.”