Dating When the Woman Makes More Money

Published On: April 7, 2023|Categories: Advice for Men, Dating Tips|13 min read|

Video Summary

Money is a touchy subject and a status symbol for a lot of people. Usually the stereotype of the man being the “breadwinner” in the dating game is often praised and desired, but what about when a woman is the one making bank? Join Master Certified Matchmaker Genevieve Gresset and Certified Dating Coach and Matchmaker Heather Drury as they ponder the dating game for women who make more money than their male companion!

Video Transcript

Heather: Hi there, Genevieve. How are you?

Genevieve: I’m good, thanks. How are you, Heather?

Heather: I’m doing really well. I’ve got a forewarn you: I’ve got a pretty lengthy letter to work through today.

Genevieve: Do I need to take notes?

Heather: I don’t know. Be prepared. Be ready. I think that this is such a topic that is worth diving into. So probably as I’m reading, you’re going to think of things in question. Okay, so the topic of our letter: “Dating When the Woman Makes More Money.”

Heather: “I’ve recently started dating in the past six months. So far, only casual which I’m not too excited about as I want a partner, but I know it’s a part of the process and I’m trying to enjoy it, which mostly I am.” Smiley Face. Good. “I’ve run into this problem in the past, but I didn’t think that it would be a big deal with men over 40. I’m not super wealthy, but I’m more than comfortable. I own property, etc. I don’t buy and wear super fancy clothes and I prefer dive bars. I’ve always been able to split the bill and wanted to on the first date. I have rarely dated anyone with a higher income than me, but often we’re in the same financial boat or are similar enough. Someone I was casually seeing for four months ghosted me after a date when two things happened.”

Heather: “One, they were visibly shaken over the idea that I would buy a $75 Uber for us. He wanted to take public transportation. It was bad weather and after 10 p.m. I didn’t even look at the price. But when he saw it, when I entered the address to our destination, I didn’t realize the price until the address page. Two, when asked why my day was so long, I explained that I’ve been asking for a raise at work because my new boss makes double my salary, which I know because the job is posted online. Very easy for him to look up and see the boss’s salary at 350,000, it would take 2 minutes. I am guessing this guy makes maybe 75,000. Whatever he makes, the idea of spending $75 on a car was unfathomable to him. I truly don’t care about his income. I just like hanging out, talking, and we were very sexually compatible.”

Heather: “What more can I ask for of a casual date?” Smiley face again. “While I know that there could be a million reasons why he ghosted later putting together these two parts of the night, I have to assume that money was a factor. I know casual is just casual, but if I could prevent being ghosted like that I’d like to try. I’m seeking advice on how to better gauge if a man has any issues with my income earlier on. What are the signs that I should be looking for beyond just bringing it up early, which feels too aggressive? Or is there no issue, no use trying to be proactive here and just it is what it is. Thank you so much for your insight.”

Genevieve: Oh, okay. Okay, I didn’t take notes.

Genevieve: Well, first and foremost, money is always a contentious issue when it comes to dating. We know that it’s unlikely that both of you are going to ever be on the same salary. So one of you is always going to earn a bit more than the other one. That goes without saying. You might be in the same ballpark, but one of you is going to earn more than the other one. And it’s interesting. This has come from a woman.

Heather; Yeah. At first I thought as reading it, it was a man.

Genevieve: So did I.

Heather: And then she threw that in there. Kind of a twist in the middle. I was like, “Oh.”

Genevieve: Hang on. I’m going to say, “Could you start from the beginning again?”

Heather: I know.

Genevieve: I think it’s interesting that the woman’s picking up that the man is feeling insecure about it. And actually, I want to say it’s actually the man’s issue. But when you’re dating casually and there’s no commitment in the relationship at all or any communication about being exclusive or committed or wanting to progress into something more than just casual, I think that creates all of these insecurities as well. It creates a lot of insecurities and you don’t know where you stand with someone.

Genevieve: So it could have been a lot of other things. I mean, she said we’re very sexually compatible. This is all from her perspective. There’s always two parts to the story. She may have done something to upset the guy and it might not have been the Uber. It might not have been money, but it could have been something else completely different. We know this from the feedback that we get from clients. One client will think one thing, and when we deep dive with the other person, they’re telling us a totally different story.

Genevieve: So I don’t want to make or draw on any assumptions in this particular case. But what I would say is if someone’s dating and again it’s that superficial ladder as it is going back to finance and money and everything else, if you’re a woman and you’re looking for someone who’s earning more than you because it sounds like she’s making a lot of this money. It’s almost as if she’s talking about how much her boss is earning and you could look it up and you can see it. So I’m wondering if the issue of money is more with her than it is with him. So I always would say: “What is more important when you’re dating?” and we know financial status is a value and money can be one of your values and that’s how you live your life. If that’s what you’re looking for is someone who’s very financially secure and stable and solid, then you need to be open by talking to someone and saying that’s what you’re looking for, and perhaps not set other people up to fail if they’re not within that category, because that’s not fair to date without intentional purpose in that way.

Heather: Right. What I like to that you said too and touched on was you might have deemed you two as compatible sexually and you’re having a great time. But what I love working through with clients, especially in the coaching realm, where we have an hour of uninterrupted time to dissect and look at and talk. Then we do follow ups and we really walk them through situations just like this. And then we might ask them, just looking at this as a situation not necessarily the whole circumstance, but looking at someone’s behavior and really paying attention to: “I feel this way” and not what words are coming out of the other person, but the behaviors.

Heather: Because there might have been a small indication that this person was not as into it as you are or were or felt. You might have been representing money on accident that did kind of annoy him and he said, “I’m good, I’m out. We’re good. You just did that. That’s that’s the icing on the cake.” So people aware of what you’re representing and looking at with just an open heart how somebody is receiving the body language that they’re giving you and their behavior is a lot more important than what people will say, right?

Genevieve: It is. But you know, what I always find fascinating is people are always very focused on what they’re saying rather than how it’s being received. Often people will go into a date and I’ll say: ‘Well, how did they respond? What was their response?” And if people say: “Well, that wasn’t much of a response.” I think it’s not really the engagement. It’s always looking for the unspoken and making sure that the two have to meet up. So words and actions have to be on the same page and saying and doing the same thing. If they’re not, then that’s something that I always question.

Heather: And the behavior of ghosting. I’m just imagining this lead up of this person that is capable of just *whoosh* disappearing. It’s a coping mechanism. We understand it’s human behavior and we’re not necessarily trying to change the world and make that disappear but if this person that you’re feeling that you have all of this compatibility with sexually, physically, intimately, which is a really big vulnerable part of relating with others. What was going on, that there was this absence of the ability to communicate? It might have just been a him problem, like you said, and really anybody’s behavior is not your problem, but paying attention to that vulnerability and that connection, you want to be able to communicate your feelings and emotions. If this person isn’t capable, then, honey, move on. Nothing lost, nothing gained.

Genevieve: I was about to say, if it’s casual, why is she putting so much into this letter? I think she was probably hoping for a little bit more than casual with this guy, because if she wasn’t bothered and if it didn’t upset her, then she wouldn’t even have written it. That’s the heartbreaking bit really.

Heather: Absolutely, and so I think one piece of advice I’d like to give to her, and you know how we are with the homework, is really start maybe journaling the thoughts and feelings you have around your personal values and your personal definition of “career” and “money.” Not society, not another guy. Don’t worry about that right now. When you have intention and you know what you’ve done to climb that ladder and get to a place where you are asking for more money and you’ve got that ability to take a hold of your career, this should be something that you’re so darn proud of. So, I’d love for her to move into identifying that and how she represents that when she is relating to other people.

Genevieve: Yeah, but I’m going to give her another bit of homework. The other bit of homework is just starting to watch other people’s body language when she’s communicating with them. So she’s starting to tune in to how other people react and respond to what she says, how she says it, all of that. I think it’s really important to know how other people see you, if you’re upsetting people, if you make people feel comfortable, if you make them uncomfortable. Because some people just walk around oblivious as to how they make other people feel. I mean, one of the things that we do in matchmaking is we look for the patterns to help people break them and then from a coaching perspective, we untangle those patterns.

Genevieve: It could be that you’re anxious and being anxious when you’re dating, you’re really thinking about yourself. You’re not actually thinking about the other person and how they’re responding and reacting to what you’re saying because you’re too wrapped up in: “Am I presenting myself well? Am I saying the right things? Am I doing the right things?” It’s a two way exchange. It’s that game of tennis I’m always talking about it. We’re not having a game of squash. It’s a two way game and a two way process. If you need support with that, get the right support before you’re putting yourself out there. Sense check it, sense check how people respond or react to you.

Heather: Right. I think these are great exercises. These are things that are simple. It’s in the grocery store and just kind of paying attention to when you see–

Genevieve: You love hanging out in the grocery store around the cheese aisle, Ms. Heather.

Heather: It’s the cheese. I always think that because I’ve kind of done a lot of personal growth and as we all have and I have found, it’s always so obvious when I just smile at somebody in the grocery store. In that passing of people that are so focused on what they need and what they need to do and life is busy. I’ve got to get home to the kids and I’ve got to prepare things and I’ve got to spend this money on the groceries, which are totally super expensive.

Heather: I’ve done kind of my own little research project to get myself a little bit more sociable, and I feel safe in the grocery store. We’re all doing the same thing. I could bring up a conversation about a tortilla, right? And it’s totally fine. So I always say that because it’s my safe place to test little things. And if I mess up, trust me I have made a complete embarrassment of myself and it’s okay because I’m not going to see that person again. So I just take the low risk environments in your life that are day to day. I know I’m going to the grocery store every week. I know I can do this on a weekly basis. I can practice this behavior on a weekly basis and come home and reflect and try again next week. That’s how easy this stuff is.

Genevieve: It really is, but practice makes perfect. If you’re not typically a slightly anxious person and for a lot of people who are dating, it raises anxieties. You feel vulnerable and you are out of your comfort zone. Step out of that slightly and just practice. The more you do it, the more comfortable it will be. When you’re out on a date, it comes across as a natural conversation rather than you trying to force these things.

Heather: I love it! When you’re calm, cool, collected and you feel good and you’re just having a good time because you’ve been practicing at the grocery store every week and you’re sitting on a date with somebody and you’re just adorable and you’re present and you’re secure, you’ve moved into that secure attachment style like we’ve talked about before. That’s sexy. That’s a good look on a dater.

Genevieve: But don’t try and fake it.

Heather: No, that’s not sexy.

Genevieve: We seen that far too many times. Just feeling confident, what we’re doing is we’re giving you tools to give you more confidence when it comes to dates. So used this to build your confidence in the dating arena and you’ll have more success. The more successful you are, the more authentic you are. You’ll attract the right person for you.

Heather: Also, think about this, letter writer, the day that you meet that man that is just in adoration of you, and so connected and communicative. You’ve got all of these things going on and then he says: “Man, I am so in awe of all of your hard work and that you are in a place in your life where you make what you have knowing now what I know you’ve gone through to get there, I just love that about you.” That’s what you deserve. So let’s work towards that and not somebody that’s so intimidated that they just disappear.

Genevieve: They ghost you.

Heather: Yep. No more ghosting. We’re going to work towards that.

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