Welcome to Hump Day, where award-winning psychotherapist and TV host Dr. Jenn Mann answers your sexiest questions—unjudged and unfiltered. Have a quandary? Email us anonymously at HumpDay@instyle.com.

By Dr. Jenn Mann
Jan 24, 2018 @ 11:00 am
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DEAR DR. JENN,

On my first date with my boyfriend, I asked for extra sauce on one of my dishes. When the waitress responded, "That'll be an extra dollar," he asked me whether I was sure if I wanted it. I didn't think much of it at the time, but here we are, one year into the relationship, and we split the bill on every date night, even though he earns more than I do. He is really tight with his money, and while there are some positives to having a thrifty partner, I can't help but feel negatively about it. I've been letting my resentment snowball, and now I don't know how to discuss this with him. Help! —Future Mrs. Cheapskate

DEAR MRS. CHEAPSKATE,

Fights about money are among the leading causes of break ups. Studies show that couples who argue about finances once a week are over 30 percent more likely to get a divorce than those who disagreed about the topic a few times a month. Finding a happy medium when it comes to your money styles, or coming to terms with one another's money philosophies, is crucial in a long-term relationship.

In this day and age, men get a lot of mixed messages about women and equality, so it's understandable that many men feel confused about how to handle finances in dating. But a year in, you are moving past the honeymoon phase of the relationship, and it's high time you let your boyfriend know how you feel. How can he please you if he doesn't know something is important to you?

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First thing's first: Examine what him paying for meals means to you. Does it make you feel loved? Taken care of? Appreciated? Do you get annoyed that he chooses expensive restaurants that you don't have the cash for? He may assume that you want equity when it comes to paying for meals. Or simply that it's not a big deal to you. Once you understand what aspect of his behavior rubs you the wrong way, you'll be able to make him understand too. The fact that you are so worried about having the conversation says a lot about your feelings about money and relationships as well. Many women who are proud to call themselves feminists feel conflicted about wanting a man to pay for dates. Is this something you're struggling with? Or is it just that money is so taboo to talk about that it makes you uncomfortable?

All that said, it sounds like your boyfriend may be struggling financially, withholding when it comes to money, or just plain cheap. It could be some combination of the above. In order to get to the bottom of this, you are going to need to have a conversation.

When you do, use what I call the "sandwich technique" in my book The Relationship Fix: Dr. Jenn's 6-Step Guide to Improving Communication, Connection, and Intimacy. Start with a positive, then move onto the "meat" of the conversation, and end with another positive. Let him know about some of the things he does well that make you feel loved and cared for. Then, share how it makes you feel when he splits the tab, making sure to own any of your own issues that may impact how you feel about this (for example, "When my Dad left my mom, he never paid child support which made me feel really uncared for, so I know men paying for me is a sensitive issue for me"). Wrap up by telling him how much you appreciate him having this conversation and how much you love him.

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Don't forget to use this discussion as an opportunity to find out what paying for a date means to him. Does it make him anxious about money? What issues does it bring up for him? In my private practice, I once had a male patient who felt that a girlfriend of his used him for his money. He was so concerned with not letting that happen again that he refused to pay for anything on dates with other women he went on to date. He had to do some work in therapy to get past his pain and better understand the warning signs he missed with his sugar baby girlfriend, but he eventually developed a more balanced financial perspective around dating.

Talking about the issue with your boyfriend opens the door for him to understand what's important to you, for you to understand where he's coming from, and for the two of you to come up with a plan that works for you as a couple, minimizing resentment.

The best possible outcome of this conversation would be your boyfriend saying, "Thank you so much for opening up to me—I would love to treat you to more dates, but I was worried that ____." Realistically, though, that's not a guaranteed result. More likely, he may express some discomfort with the idea of being expected to bear more financial responsibility. Try to understand his perspective rather than taking it personally because there are lots of ways to come to a resolution—you just need to find the one that works for both of you.

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One option is to take turns paying for and planning dates. This works especially well if your resentment is less about the financial cost of dates and more about the value he places on showing you that he appreciates you. Choose a date activity that you feel comfortable organizing and paying for top to bottom, whether it's an expensive restaurant dinner or a day hike with a packed lunch; next date is his turn. Or suggest that since he earns more than you do, you should each contribute a percentage of your paychecks toward a "date fund," which he can pull from when he's paying the check.

Everyone likes to be shown affection in different ways, and that's the point you need to clarify for him—this is an important way to communicate affection to you, even if it's not his default way to show it. By that same token, he may not care whether you spend money on him but may want to see more love from you in another way. Ask him how, and you may find that both of you have an opportunity to turn up the romance with a few simple adjustments.