Who Pays the Bill When You're Dating After 50?

Date No. 3 and beyond. Over time, some couples default to having the person who makes the most money pay more often. And if the person who makes more is used to a certain level of dining, for example, then it makes sense they would cover the cost, says Katy Song, chief financial planner at Domain Money, a financial planning firm based in New York. This comes up not just in dining, she adds, but also when it comes to vacations.

Other couples prefer to keep splitting things down the middle or taking turns no matter what the financial differences.

Bring up the past

Money habits can be something deeply ingrained in someone from a young age. One good way to learn about someone’s current money philosophy is to inquire about their past.

“Find out how you respectively lived and grew and learned about money growing up,” suggests Sharon Lechter, co-author of Rich Dad Poor Dad and How Money Works For Women. This is a great way to open up the dialogue and get talking about your spending habits, saving habits, and your overall attitude about money. You don’t have to have the exact same money habits to make a relationship work, but you do need to respect and understand each other, adds Song.

Plan a nice dinner, sit down with a glass of wine, and ask the other person: “So, how did your parents handle money?”

Before you start this conversation, though, says Song, take inventory of how you are with your own finances.

“By understanding each other’s money habits and position in a non-judgmental way, you can have more fun and embrace the newness of sharing your life with someone at this stage when you know yourself so much better than you did 20 years ago.”

Get a feel for what you both like doing for fun

Ask a potential partner how they spend their free time and use that as an opportunity to pick up clues about their lifestyle. This can be a good way to gauge what kind of spender they are and if your priorities about money are compatible, says Lechter.

For instance, if someone says they go to the bar a lot or drink a good glass of wine every night, you can assume they prioritize spending money on alcohol. If they talk about expensive hobbies, like golf, you’ll know that they like to spend money on tee times and perhaps club memberships. And if someone talks about taking trips, then it’s safe to assume that travel is a favorite way for them to spend.

Money aside, this is also a chance to see if your interests vibe. If your potential partner is obsessed with golf and you can’t stand it, or hates traveling and that’s your main priority for your retirement years, then you might not be the right fit.  "Being adaptable is a key relationship skill, but when you're over 50, some people become ossified or 'set in their ways,' ” adds Davis.  “By your 50s, people might have their minds made up about what they like and don't like.”

Talk about what your financial future looks like — retirement included

In your younger years, you wouldn’t get serious with someone without having the “Do you want kids?" talk. The same thing goes for money. At some point, if things are headed in a forward direction where there’s talk of living together or marriage, make sure you’re on the same financial page.

“Most of my clients at this point in life are less interested in combining finances if they are both working,” says Song. Others, however, may still want to go the traditional route. Regardless, if things get serious, it’s a good idea to know where you both stand. “Moving in together is a big deal and can be made easier with an open discussion about finances and mutual assurance that each partner has their money in order,” adds Song.

And the biggest difference between money talks at 50-plus versus those in younger years comes down to one dominant issue: retirement, says Davis. “You don’t want to be on track for 60 and travel the world, and then learn your partner never wants to stop working,” says Song. “This is a potential big obstacle.”

Be clear about financial assets — and debts

Everyone arrives in a relationship with a financial portfolio — whether it's good, bad or somewhere in between. It’s important to be clear about what that looks like as the relationship progresses.

“They're probably coming together with certain assets or debts, maybe some pensions, maybe they have a divorce where they have liabilities, like taking care of kids,” she explains. All these topics have the potential to cause stress in a relationship if they're not discussed upfront, says Davis. So have those conversations and come up with a plan on how to handle them.  

Lechter shares the following as an example: If you're dating and getting spousal support and you decide to get married, that spousal support will more than likely end. Sometimes, it even ends if you're cohabitating with someone.

“It's really important to understand the baggage you're bringing to the relationship, both the assets, the debt and any restrictions on what the debts and liabilities and ongoing responsibilities and marriages, depending on what you look at,” she explains. Money, she adds, is a big reason people divorce, so it’s really important to be open about it.​