How to Navigate the Financial Side of Dating

Money’s difficult enough to deal with on your own. Add dating to the mix and you’ve got a whole host of potential headaches on the horizon.

Dating is tough. And it’s been tough forever. Cave people never knew when a lovely, romantic evening would be interrupted by a rampaging woolly mammoth. An Aztec couple holding hands as they walked next to the waters of Tenochtitlan didn’t know when their stroll would be interrupted by a rampaging conquistador. And good luck convincing anyone to get a cup of coffee with you when you’re suffering from the Plague.

These days, dating isn’t quite as deadly, but it still has its own set of issues to navigate. And one major vector of those issues is financial. Money can be awkward to talk about, even if it’s with someone you’ve known for a very long time, let alone someone you’re meeting for the first few times.

But fear not! We’ve got experts in both dating AND finances, and they’re here to help!

Who pays for dinner?

We’ll just get the most obvious question out of the way first. Who should pay for the meal?

Almost a century of conventional dating wisdom maintained that the man would pay for the meal. But there are clearly a lot of reasons to reexamine this assumption. Most glaringly, there could be two men on the date. Or no men! Beyond that, this standard was set when the expectation was that men were the ones who worked and pulled a paycheck and women generally did not.

Thankfully we’ve made a lot of progress since that time, but it does mean you may have to consider some different approaches when it comes to the cost of the meal.

“When going on a first date with someone, typically, the person who asked the other out should pay for the bill,” Holly Zink, a lifestyle expert for Kiwi Searches (@kiwisearches), told us. “However, if the tab is a lot, the check should be split. After the first couple of dates, you can alternate between who pays the bill. From a woman’s perspective, it’s always a turn-on and chivalrous when a man at least offers to pay.”

Another contributor also offered a positive take on the traditional approach.

“When you’re first dating, and the first date in particular, who pays can be about as awkward as it gets,” cautioned Vivek Jain, CPA, co-creator of new dating app LOKO (@LOKOforlove). “I’m old fashioned when it comes to this, so I’m of the belief the man should always pay for the first date—at least make that gesture—and if it leads to a conversation then who ultimately pays how much can be decided together.”

There may not be one approach that will work for any given two sets of people, but the most important thing is to communicate openly, especially if you’re hoping these early dates could grow into a relationship.

“If you find that you are wanting to enter into a long term relationship with one another, alternating paying the bill, or always splitting half and half can be something you discuss,” advised Justin Lavelle, Chief Communications Officer at (@BeenVerified). “This issue is really best decided by the parties involved. Everyone is different, so it is important to set feelings and boundaries early and as they come.”

Money issues can persist past the first few dates.

Katie Ziskind, therapist and owner of Wisdom Within Counseling, explained how these seemingly simple financial conflicts can actually reflect deeper financial anxieties a couple will have to reconcile if they’re looking to stay together:

“When I see couples in my therapy office, financial issues are a big topic. If one person in the couple makes more money, often this person will pay for dinners out at restaurants. This is often a couple that has been together long term.

“However, even if this is agreed upon, the person who makes less money still has to process their money issues, shame about not making as much money, and the feelings about their childhood and how money was used in their family growing up.

“Money issues are rooted deeply back into childhood and often relate to how money was used as a privilege or a form of love. Some families use money to replace emotional connection, which leads to issues in romantic relationships as adults.

“If you grew up without having a lot of money, and now you have a great job, you may feel very proud to pay for yourself or for your date regardless of your gender.”

Talking about the future.

Communication only becomes more important as the relationship grows increasingly serious. It’s good to start having these conversations early on, though it may be good to take a light touch.

“You can mention your future goals, and make implications about money, early on in the relationship without necessarily making it a conversation about money,” suggested Leslie H. Tayne Esq. (@LeslieHTayneEsq), Founder and Head Attorney at Tayne Law Group (@taynelawgroup).

“For example, you can mention that you’d like to settle down in a different state eventually. This is a general statement about your future goals but implies that you’d probably like to buy a house and will need to pay for the move.

“As the relationship progresses, conversations about future goals should become more explicit. Having differing goals for the future can be a major problem in a relationship and is something that should be addressed as early as possible.”


When you get into a relationship with someone, you’re also getting into a relationship with their debt. So it’s good to know what you’re both getting into at the start.

“Debt can be a tricky subject when dating, particularly if one or both of you have a lot of it,” warned Tayne. “Once again, honesty is the best policy, particularly if the relationship is on the path to being a serious one.

“You don’t necessarily need to reveal your entire financial situation right away, but being upfront about the fact that you have debt will allow you and your partner to navigate the financial aspects of your relationship.”

Gifts of a fun guy (or girl).

Giving gifts can be an important part of both emerging and long-running relationships. But it’s also yet another area where financial awkwardness can rear its head.

“When dating someone, that person will likely give you gifts,” Zink explained. “However, if these gifts are way too expensive or they are given too often, this is a money concern to address.

“To start, show your appreciation and gratitude for the gifts. Then, discuss with them some ground rules for gift giving, such as only giving gifts on holidays, birthdays, and other occasions.”

Moving on in.

If you’re together long enough, you may consider moving into the same place. As you could probably guess, this also comes with its own set of financial challenges.

“Living together presents even more financial possibilities,” warned Lavelle. “Does one of you want the other or want yourself to be the established breadwinner? Are you both in agreement on one of you paying the lion’s share of the household expenses? If not, set up a reasonable budget that the two of you can afford while contributing equally.

“There are many ways to split up expenses, so be sure to communicate and be honest about both of your expectations and abilities. Maybe one of you makes significantly more and the other is struggling to pay half of everything. If this is the case, the one making less can try taking on one or two smaller bills instead of half of all of them.”

Finding the right person would be difficult even if money weren’t a factor. While we can’t help you find “the one,” these tips will hopefully make navigating the money part of dating a bit easier. To learn more about managing your finances, check out these related posts and articles from OppLoans:

How do you handle money issues when you’re dating? We want to hear from you! You can find us on Facebook and Twitter.

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Vivek Jain is a seasoned entrepreneur and finance executive. He is the co-creator and CEO of LOKO (@LOKOforlove), the first video-only dating app on the market. Prior to focusing his time on LOKO, he co-founded what has now become the Fan-Controlled Football League (FCFL) after spending a number of years in venture capital and finance.
Justin Lavelle is a Scams Prevention Expert and the Chief Communications Officer of (@BeenVerified). BeenVerified is a leading source of online background checks and contact information. It helps people discover, understand and use public data in their everyday lives and can provide peace of mind by offering a fast, easy and affordable way to do background checks on potential dates. BeenVerified allows individuals to find more information about people, phone numbers, email addresses, and property records.
Leslie H. Tayne, Esq. (@LeslieHTayneEsq) has nearly 20 years’ experience in the practice area of consumer and business financial debt-related services. Leslie is the founder and head attorney at Tayne Law Group (@taynelawgroup), which specializes in debt relief.
Holly Zink is a tech and security expert for Kiwi Searches (@kiwisearches). She is up-to-date on the latest security issues, from online scams to identity theft.
Katie Ziskind is a licensed marriage and family therapist, a 500-hour registered yoga teacher, and owner of Wisdom Within Counseling. Wisdom Within Counseling, near East Lyme, Connecticut, is a practice that uses a holistic, integrative approach. Art, yoga, music, and outdoor therapies are woven together with talk therapy. Additionally, Wisdom Within Counseling is an LGBTQIA+ friendly and advocates for youth and adults. Teletherapy and distance options are available.

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