Singles today, especially those over 50 and raised with more traditional values, often get confused about who should pay on dates. With women now making up 47% of the workforce, many being the sole breadwinner or highest earner in the home, old assumptions about who is paying for what and for whom have all but gone out the window leaving many singles scratching their heads. 

The problem is even the strongest, most financially independent women sometimes want to feel taken care of, while the most manly of men don't want to feel taken advantage of by always picking up the tab. At the same time, men who earn less than their female counterparts also struggle with how to assert their masculinity in ways other than through their wallets without appearing cheap, while financially well-off women don't want to become victims of financial abuse by men. The result is a lot of missed signals.

As a matchmaker who has been helping women and men find love for nearly three decades, I can help uncross these signals by helping you answer a few simple questions. Here they are.

Who pays on the first date?

Let me keep things simple for you: men should always pay on the first date. Tradition is still tradition, even in the modern age. However, don't take advantage of this tradition or your date. Be prepared for the man who expects to split the check, or maybe even for you to pay. Don't show up without your wallet. As a general rule, always have money on-hand in case of emergencies. But I digress. 

Even if the man does pay for you on the first outing (which, again, I believe he should), as a courtesy, don't make the date expensive. Avoid dinner dates. Instead, do wine. If the date is going well, you could consider ordering an appetizer. But by deliberately being a "cheaper" date, you will do a lot to prevent the man from feeling like you are taking advantage of him.

Who pays after the first date?

This is when situations get murky. Call me old-school, but I believe a man should court a woman. A man should feel like a man, and a woman should feel like a woman.

That said, don't exploit the courting process. Some women like to joke that men are naive or whatever else, but as human beings, we can feel when someone is using us. Yes, that includes men. Being used for your money (or anything else) is a terrible feeling. If you are using your date for expensive meals, he will figure it out. He will feel lousy about himself, and, as a result, he will no longer wish to date you. In short, let the man court you, keeping in mind not every date needs to cost an arm and a leg, nor should it. Wait until you are more comfortable with your date before ordering the surf and turf. 

How can a woman contribute financially early on while still letting a man be a man? 

It's the early stages of dating, and my man has been thoughtful and generous with his time and money, so how can I show my appreciation? There are countless ways, and showing gratitude allows a woman to be creative. Make dinner (if you are comfortable). Get tickets. Pack a picnic lunch and go for a walk or hike. Perhaps pick up the tab for drinks or coffee and dessert.

Doing fun things with and for your date will not only help you express gratitude for him paying for your meals, but it will demonstrate your further interest. He is investing his time and money in you, and by planning fun activities and dates with him, you are investing your time and money, too. On top of it, you will get to know each other better and be able to develop a deeper bond than you ever possibly could over dinner.

Who pays once you are in a relationship?

Now is the time when you set your own rules based on what is comfortable for both of you. Once you are in a relationship, you should talk to your partner about the financial logistics of dating. Just as important as talking to your partner is, you should listen and make compromises as well. Being in a relationship means you need to consider the end game. Are your goals the same? If so, fantastic. Do what works for both of you. If not, you have a lot more important questions to answer than who should pay for dinner.