How a New Relationship Can Trigger Money Issues (Plus, How to Prevent It)

November 11, 2015

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A couple, I’ll call them Tom and Sally, get together for a second date, wine, and appetizers. They had gone out for coffee a few days earlier and shared an immediate sense of having met someone special. Sally had mentioned she’d be traveling for work; they would not be able to see one another again for more than a week. Tom decided to find out if his initial feelings about Sally were true. So he asked her out three days later. Glad that he’d taken the initiative, she happily accepted.

Now, on that second date, they are savoring each other’s company when the check arrives. Neither one makes a move. There is an unspoken moment of uncertainty. What to do? In this case, Tom and Sally brought very different expectations to this situation, which triggered intense feelings on both sides.

Cliché as it is, there is no doubt that the times have changed, especially when it comes to the assumptions about who pays on a date. Gender roles are evolving in every area, from work, to family, and relationships. The notion of gender identity itself is no longer fixed.

With the arrival of the check, suddenly, a gaping chasm opened up. This could get the relationship off to a bad start. As we’ll see, it ended up leading to a very interesting conversation about money.

Sally excuses herself to the restroom. Tom is feeling pretty good about the chemistry between them, and is confident Sally wants to see him again. Temporarily waiving his reservations, he pays while she’s away.

But the incident about the check nags at him later. He recalls Sally telling him about her successful marketing career over the last two decades. She certainly seems independent and self-assured. Why, then, didn’t she at least offer to split the tab on their second date? He feels very much at odds with the stereotypical dynamic in which the man pays for the date, with the tacit assumption that he will be “thanked” later with physical favors. It seems disrespectful, to both parties. The expectations on both sides continue to irritate him as he thinks about the situation and its implications. If a woman did not at least offer to pay half, was she just looking for someone to pay for her dinner; or worse, was she someone who just wanted to be taken care of?

Meanwhile, what is going on in Sally’s mind? The following day, Tom sends her a note saying how much he enjoyed seeing her. He also makes a comment about feeling triggered by the payment situation and wanting to talk about it. Sally’s perspective on the issue was that, because Tom was the one who had asked her out, she assumed he would pick up the tab. After all, that’s the way it was when she was growing up, and now, even decades later, that was still how she saw it.

Their third date is a walk on the beach. While enjoying the view, Sally says, “I think I have some issues around guys and money.” She proceeds to tell the story of her relationship with her ex-husband. For many years she was the one who supported the family, which included her ex and their school-aged daughter.

When Sally told her ex-husband that she wanted a divorce, she was shocked to find out that he had already consulted an attorney. He informed Sally she would likely be obligated to pay him spousal support, and she was outraged at the idea. Not only had he not contributed to supporting the household during the marriage, but he also expected her to continue to support him after the relationship was over. Tom acknowledged that this must have felt like rubbing salt into the wound.

Tom then shared some of his story, which included being a frugal saver. He admitted that for much of his life he had harbored the fear that there would never be enough money. His divorce had put him in the position of starting over, making these feelings even worse. Now that he was dating, he was looking for someone who could take care of herself. In his mind, if a woman didn’t offer to split the cost of a modest meal out, she probably expected to be taken care of. Sally acknowledged how not offering to split the check could have pushed his buttons.

Ultimately, this discussion was not so much about who should pay, but more about the feelings that can arise around money based on each person’s past experiences and beliefs. Projecting these emotions onto the situation without examining them can derail the relationship before it even gets started.

As it turned out, Tom and Sally were able to listen to one another and acknowledge the other’s point of view about what had occurred. They both agreed it was important to be open and to speak their truths. Each cared enough about the relationship to be honest and vulnerable.

Tom and Sally’s opinions and feelings about money may not necessarily change as a result of their conversation, but they were better able to empathize with one another as a result. Bringing a sensitive issue to light can begin to defuse its emotional charge. While such conversations can be difficult and feel very risky, they can also lead to a new level of intimacy. Tom and Sally’s conversation ended with warm hugs and a deeper appreciation for one another.


Jeffrey Stoffer is a member of the DailyWorth Connect program. Read more about the program here.

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