DISCLAIMER: The following may be controversial, but this article is in response to clients who have requested us to write about this particular subject from a more traditional point of view. Rest assured, that we at the Workman fully agree and support gender equality. 

This particular question probably goes through your mind every time you begin to date someone new: should I be offering to pay for everything? Well, the answer can be straightforward yet complex at the same time; so read on and find out the answer to your question.

Let’s get this out of the way, when you take a girl out the first few times, let’s say the first 6-8 times, you should always, always offer to pay. I’d even go further and say to not only offer, but to expect and want to pay for everything. But why should you pay? Well, you should pay because treating someone out to something is a sign of respect and appreciation toward that person, and doing this is a tangible way for you to show that (even with friends).  You see, if you’ve already been on a few dates, that means you’ve already past the “does she like me” phase. The fact is, if someone is willing to see you this many times, you obviously mean something to her. So yes, you should consider paying for everything the first few times.

There are many reasons why you should offer to pay, these include:

  • It shows that you respect her and her time. For most people, making money is a grind. Everyone has to deal with whatever problems they have at work, so spending your hard earned money on someone is you inherently saying, you’re worth my time. Therefore, treating her out to a nice meal or something is showing her your appreciation.
  • It’s what a gentleman would do. She may not accept your offer to pay, but you must always offer. Unfortunately, dating has become very pragmatic. You swipe left or right to get what you want, and if you don’t want something, you just close the app and forget about it. Paying for dates is similar in this vein. She may feel offended if you paid for her or she may want to feel your equal and offer to split, whatever the end result, you should as a gentleman always offer to pay.
  • You feel good about yourself. As the old saying goes, it’s better to give than to receive. There is something special about treating someone; there is this inherent feeling of satisfaction and pride. Remember that feeling when you received your first ever paycheck and you treated your loved ones out to a meal? Well it’s the same feeling with someone you’re interested in. Treating her should and will make you feel good.

For further clarity, I’ve added a small list of things you should expect to pay for.

Here are a few things that you must offer to pay for:

  • All the meals. These include brunches, dinner, carnival snacks, food festivals, food trucks, etc. Whatever date you’ve planned.
  • All the drinks. These include happy hours, night clubs, cocktails, and if she wants you to meet her friends, you must pay for them (as she may be testing you and you want to make a good impression).
  • Anything that requires a ticket. These include museums, the cinema, a show, a music club, theme parks if that’s your thing, etc.

Here are a couple of general things that you don’t need to offer to pay for in the beginning:

  • Her personal items. If she wants you to buy her everything from the beginning, be wary my friend.
  • Her guy friends. I would advise against this, but it’s your call. If they’re really friendly and seem genuine, then by all means. If they’re arrogant and they’re sizing you up, don’t do it.  Be nice, but they can pay for themselves!

Now you’ve got the easy answer, you should always offer to pay for everything during the initial parts of the dating life. But here comes the hard answer. As a relationship matures and develops, you should be asking yourself the same question: should I be paying for everything? The answer to this question is entirely up to you, but the bigger question to consider is, what type of life do I want?

I am a firm believer in having fun and dating around, exploring the world and experiencing as many people, personalities, and cultures one possibly could. All this with the ultimate goal of finding someone to love and to cherish, finding a true life partner.

It goes without saying that relationships hinge on a variety of different issues, personality differences, hobbies, moral values, etc. There are so many variables that can make or break a relationship, but as it pertains to this article, we’ll continue with the issue of finances. When you date someone for long enough and deeper feelings start to develop, you must ask yourself whether this person is someone you see as a life partner. Do you see this person as someone that helps you and relieves stress after a long week? Or is being with this person going to stress you out even more? If you lost your job one day, would she be sympathetic or would she put you in panic mode?  A lot of relationships fail because of finances, how people spend money and what they spend it on. Who’s making the money and who’s spending the money? These are all important questions you must ask yourself as you grow in a relationship, and knowing what you both want is the key to a successful relationship.  

Dating is easy, but love is work. Anyone that tells you otherwise is lying. So should you pay for everything? The easy answer, in the beginning, yes you should. But as your relationship matures and you ask yourself once more, should I be paying for everything? The harder answer, yes you could, but at what price?


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