Who Should Pay On A First Date

When I first started dating after my divorce (and was utterly clueless), one unexpected thing that really got me feeling uncomfortable on every first date was: who should pay??

Social norms from back in practically the Victorian era when I had last dated dictated that men should pay. But we’re in the age of female empowerment! Shouldn’t I pay? Or at least offer to split?

I wasn’t sure what was normal, so I turned to my one of my single friends at work who was also online dating.

“You shouldn’t even offer to split the check,” she told me. “Men want to pay!”

So I sat on my hands when the bill came and wouldn’t even reach for the check. It felt unbearably awkward, but this was what men wanted, right?


Someone who declined a second date with me finally – very gently! – alluded to the fact that it was off-putting that I didn’t at least offer to split the bill.

It was a lightbulb moment for me: both that it was polite to offer to split the bill, and that I could trust my gut when it came to dating. I like to offer to split the bill, so I should show that part of my personality, and not try to guess at what’s “normal” in dating.

So, Who Should Pay On A First Date?

Here’s the bottom line: the dance around the bill should be polite and in your comfort zone. Sometimes that meant my date generously insisted on paying; sometimes we’d split the bill. And often on the second date, I would insist on paying and that felt majorly empowering (albeit not easy for a single mom on a budget!).

Looking for more guidance? Here are my tips :

  1. Tip: Avoid dinner first dates

Many of my clients – mostly men, and mostly over 45 – were trained on the idea that a first date should be dinner. But dinner gets both expensive and lengthy fast. Stick to drinks for a first date. It’s easier on everyone’s wallet and sets you up for a more graceful and timely exit if there aren’t fireworks. No need to stick around through multiple courses! 

  1. Tip: Order early

This tip is (mostly) for the ladies: if you want to avoid the “who pays” conversation altogether, get to the bar a little early, order your drink, and pay in cash before your date arrives. Then you can suss out the “who pays” vibe only if there winds up being a second round 🙂

  1. Tip: Don’t Venmo

Why? Read about it here.

Bonus Tip: Click here to hear how our all-time favorite online dater, Carol Mills, handles paying for that first-date drink.

My Mindful Dating 101 course has an entire module on navigating things like this that have the potential for awkwardness on an early date. Learn about the things that might throw you off, and how to savvily navigate any dating situation that can come your way.

dating profile in an hour course


Purchase our Profile In An Hour, designed for getting your profile swipe-right ready in as little time as possible.


Hi! I’m Alyssa Dineen and I’m a personal stylist and dating coach all rolled into one. I started Style My Profile to help other online daters feel better about getting out there— and staying out there— in the world of online dating. Whether it’s to meet your soulmate, to find a fun person to have dinner with or even just match with more people, I can help you from the ground up.


dating profile in an hour course


Purchase our Profile In An Hour, designed for getting your profile swipe-right ready in as little time as possible.