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The Guys’ Guy’s Guide to Love and Money


Once upon a time, guys paid for everything. And women were not your bosses. And jobs were not downsized and replaced by robots.

Life was so simple. Or was it? All the changes that have occurred over the past thirty years have reconfigured our lives and how men and women relate to one another. But throughout it all one thing has not changed. Money can still have a major effect on a relationship. So you better get on the same page with your partner when it comes to managing the cash. I’ve lived, loved, and learned a lot about money and relationships throughout these past three decades. Now I’m taking this opportunity to share a few secrets about how to make your relationship thrive when it comes to dealing with financial issues.

Surprisingly, the key to success isn’t necessarily tied to how much money the man or a woman earns. It’s more about the ways a couple share certain values about money. If they do, they can turn their love into a true partnership where everyone wins. But there’s no one size fits all solution. The world is a different place now, so if you are a guy, your partner may now earn more than you. And that’s one reason that couples need to be flexible about how they view cash. So, here are my insights in what I’m calling The Guys’ Guy’s Guide to Love and Money. To help clarify some of the issues and nuances I’ll segment my tips into three categories:

1. Dating – The best time to set the tone for dealing with money in a relationship is at the beginning. Although for the most part men still earn more than women and unfairly still get paid more to do the same work, many things have changed over the past thirty years. Back in the day, a guy would ask a woman out and pay for the date. It was accepted and expected. Nowadays, people meet online or through apps for a meet up, a coffee, or even a quickie. So things are more fluid.

And there’s more. Today’s young women are entering the workplace more educated than the guys, and are making more money than ever before. They don’t need a guy to take care of them financially like their parents’ generation rolled. But, that still does not mean women want to pay their equal share.  I’m not judging, but because of this perceptual selectivity, things can get off on the wrong foot and pretty sticky if a few ground rules are not put in place.

To make things work right from the start, I suggest that when a guy asks a woman out for drinks, coffee, or dinner that he pays for it. It makes sense, and who wants to end a first date on an awkward moment when the check arrives? Guys, suck it up and pay for that first date. After that, if you want to get together again, set up another date and when the bill arrives, don’t flinch. Reach for the check again. One of three things will happen—she’ll either let you pay, she’ll offer to split the tab, or she’ll pay for it herself. At this stage of the game, it still doesn’t matter. You can easily pay for a second date, so pick up the check and don’t sweat it. After that, you hope she comes up with a plan to treat you right, by maybe offering to take you out or inviting you over to her place for dinner. Any of those options is a good thing because what you want is a natural, comfortable flow where mature adults deal with money like champs and money is not an issue. Based on who earns more money and other factors, a pattern usually surfaces that suits both of you. However, if she never picks up a tab or makes you dinner or comes up with something to contribute on her own, it’s a potential red flag. The truth is that some women, regardless of how much money they earn, still feel that the guy is responsible for all of the cash outlays in a relationship. If that turns out to be the case, then you have to decide if that works for you. If you run a hedge fund and she’s a teacher, it should not be an issue. But if you are both earning about the same amount and she expects you to pay for everything, you’ve got to determine if it’s a workable situation. In my experience, all the cool women I’ve dated were chill when it came to doling out the cash. I’ve dated a few women who never reached for the check or never even baked me a cupcake. Over time, it didn’t feel right so I moved on. But, that’s just me. You have to find a happy place based on your income and what feels right for you, and for her also. If you like her, but she never, ever picks up the tab, there is nothing wrong with bringing up the subject, although it can be a touchy area that could become a deal breaker. But that’s better than avoiding a potential sore point.

2. Committed or co-habituating – In all likelihood, if you’ve gotten to the point in a relationship where you are committed or living together, you probably have a grip on the financial aspects of your relationship. Most likely, you have fallen into a groove where and you pay for different things. Maybe you pay the rent and she pays for groceries and cable. Or you pay for dinners out and she buys the groceries. Or, she moved into your pad so you handle the rent and she pays for utilities and meals. Whatever. The point is, by this time if you are in a real partnership you most likely have sorted out the money issues.

But, maybe not. There are many variables to consider. What if you bought a condo and she moves in? You pay the mortgage, what does she pay for? Does she expect to share the equity built into your place because she is living with you? Do you charge her rent? Will she be resentful if she pays you? Every situation is different, but one thing is for sure. You need to work out what feels right and consider any and all potential scenarios if you are living together or preparing to take that big step in a relationship. Like most things in life, it’s all about anticipation and expectations, so put on your thinking cap and make sure you have a fair-minded system that works for both of you. The last thing you want is for your partner to latch on to feelings of unspoken bitterness. That is often a silent but deadly relationship killer. Trust me. I’ve been there. Get your perspectives out in the open and be willing to discuss what you feel. Whatever you do, come to terms with a mutually agreeable solution before shacking up.

3. Married – Marriage comes with a whole new set of financial considerations. Many couples these days have at least one partner who has been previously married. They may have kids, or have a very specific set of financial issues they are dealing with. So when you marry, it’s good business to get full disclosure about their fiscal obligations, especially if you’re planning on pooling your assets.

There are a number of ways to make things work. Because life gets so complicated many older couples sign pre-nuptials before marrying a second or even a first time. You’ll need to determine if pooling your assets or maintaining separate bank accounts is the way to go. There are benefits to both paths. Couples usually save money when they jointly file their taxes, but that does not preclude their maintaining their personal investments, bank accounts, and credit cards.

And it’s only fair to consider these options, especially if one person has been very diligent about his or her credit score and savings while the other may play things a bit more fast and loose when it comes to managing debt and doling out cash and managing their lifestyle. There are huge discrepancies in how we spend money for what some consider everyday purchases where others consider those same things as unnecessary. Take coffee as an example. If you buy a good brand of coffee, brew it at home, and fill up your thermos each day you can save at least twenty bucks a week. That may be a drop in the bucket for some, but now add in the savings from making your lunch at home versus paying twelve bucks for a chopped up salad in a plastic container every day. You’ll probably save close to another fifty bucks a week just by schlepping your lunch to work.

The point is, the little things add up so make sure you and your partner are singing off of the same song sheet when it comes to how you two spend your cash. You don’t want to quibble about take out food, but if you are not paying attention, you may see your pile of dough sink a lot faster than you anticipated, mainly because you are no longer solely in control of it. The older I get, the more sense it makes for couples to maintain separate checking, savings accounts, and credit cards. This way you don’t have to totally freak out by having to see your partner’s purchases, although in reality you are probably sharing the costs of everything. You just don’t have to have the your partner’s purchases rubbed in your face all the time.

I’m a good saver so keeping some things separate has proven to be protective of the partnership. I do my best to maintain a cushion of savings for when things go haywire, which they often do. These days, people lose their jobs and change careers in a flash. That means couples need to be in synch when it comes to managing their money, and even more so when kids come into the picture. So think things through and talk about financial issues with your partner. You don’t want surprises. I promise you if you keep the lines of communication open it will eliminate most of the stress when things get random.

When it comes to money, whether dating, living together or married, couples need to find out what works best for them. We live in a capitalistic society driven by consumerism. There is no escaping our needing to face down various financial situations almost every day, including those inevitable rainy days, too. Think about money, talk about it with your partner, and get on the same page. When it comes to love and money, communication is the only way to make things work. Good luck.

This week’s GUY’S GUY of the WEEK are all the couples who have found a system, a formula, and a way to co-exist in a financial partnership built on their love. It’s never easy, but it can be done.