The Dating Game: Should I Pay?

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“We’ve been dating for a few months now and I feel bad that he pays for everything. Should I offer to pay?”

Dating is already a delicate and even tricky scenario.  I marvel at anyone who genuinely enjoys dating.  Once you have exclusively dated someone for a while and there is a comfort level– then it becomes fun. But the stages leading up to that can be exhausting.

Does he like me? Is this a date or a hang out? Should I say something? Is he going to ask me out again? Do I want to go out with him again? Can I go out on dates with multiple guys around the same time, or can I only date one guy at a time?  The questions are endless and tiresome.

And then we add money to the equation.

Dating is expensive! As a single gal, I never truly considered how much money a guy would spend on a date night– a night including dinner, wine, dessert and entertainment could easily cost a dude $100 or more.  It wasn’t until I was married that I began to truly gawk at how much money my husband and I can drop at our favorite restaurant. My husband also loves to remind me how strapped for cash he was at the beginning of our dating phase.  He would take me out on a lavish date and then eat progresso soup for the rest of the week!  Of course, I had no idea at the time that he was blowing his weekly food budget on me each date night.

So, girls, when you’re out on a date, should you offer to pay bill?

First let me say– I don’t think there is a wrong answer here.  I know some folks feel very strongly one way or the other, but you do you.  If offering to pay sounds kind and considerate– do it.  If it appalls you, don’t do it.  The most important part of dating is that you are the real you– so don’t do something (or not do something) because you think it’s the “right” thing to do in this crazy game we call dating.  Just be you.

That said, of course I have an opinion on this and will give you my two cents (pun intended).

1. Who pays on the first date?

I’m of the opinion that if a guy asks you out on a date, he will pick up the bill.  That said, I have offered to help with the bill before.  I don’t reach for my wallet or play some kind of weird charades.  When the check comes to the table, I point to it and say, “Can I help with that?”

They always said no.

Now for me, if a guy had looked up and said, “Uh yeah, that’d be great!” I would have graciously and gladly paid (after all, I did offer– don’t offer something you aren’t ready to follow through with) but I would probably decide based on that alone, he’s not the guy for me.  Perhaps that seems harsh– but I wanted to date and marry a guy who was glad to pay, generous, and for lack of a better term– traditional.

2. What if I, the girl, ask him out?

I will be honest– generally speaking, I think you should let guys lead and do the asking.  If a guy likes you, he’ll pursue you.  He doesn’t need your help.  And you don’t want to be the girl who has to lead him all the way to the altar.

Now, I am not against giving guys a strong signal by suggesting you’d like to go out or for him to call you sometime. Truth be told, I did this with my husband– I reached out to him and suggested we grab a drink and catch up.  When the bill came, I was fully prepared to go dutch. Of course, my now-husband reached for the bill and completely dismissed my offer to split it.  (Insert heart eyes here.)

3. What if we’ve been dating for a while?

A “while” is relative, but you’ll know when you hit a spot where you start feeling like, “I should probably start chipping in.”  I don’t think I ever paid for a “restaurant dinner” kind of meal, but at some point I started offering to pick up the ice cream, coffees, or take out tabs.  Sometimes Tyler let me, sometimes it was a sneak attack on my part. I wanted to contribute, but he also still wanted to be the kind of guy who paid.

My husband likes to really push guys to “take care” of their girlfriends during the dating season.  He challenges them to do this by always paying, constantly serving, meeting her love language (whether thats gifts, quality time, etc).  For him, it’s the beginning of a lifestyle where you are always thinking about and meeting the needs of your wife.  “Happy Wife, Happy Life!” he likes to sing.  But all of that starts in the dating phase.


I have a dear friend who loves to pick up the bill when out with friends.  If you fight her, she’ll retort,

“Don’t steal my joy!”

I love that.  If it gives your man joy to pay for everything– just let him.  You don’t need to pay in order stand up for women’s rights. I do think most men are wired to want to lead and provide in dating/family relationships.  While you are perfectly able to do both of those things yourself, let him act the way God created Him to be.  Don’t steal his joy! But if he is open to letting you help out with the bill, don’t scoff either.  He may just be more strapped for cash than you think!

No matter what, just be you and let him be him.  Even when it comes to money– which though a seemingly small thing in dating, is actually a pretty major issue in marriage–There is nothing more important than simply being your true self so you can both know whether you want to date this person forever.

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