Should You Let Someone Pick Up Your Tab If You Meet Them “In the Wild”?

Alright, let’s talk about a different kind of “picking up the tab.”

I’ve already shared my opinion on who should pay during the courting stage—that window of first dates before you’ve both agreed to exclusivity (which, for me, is about six to twelve weeks of seeing each other). In that stage, yes, I believe the man should take the lead.

But what about when you’re not on a date at all—when you’re out on your own or with friends, and you meet someone “in the wild”?

The Classic Bar Scenario

If you’re somewhere with more cocktails than entrées, you may get the age-old move: the bartender slides you a drink “from him.” By the time you know it’s happening, it’s done. At that point, a smile or a nod is enough. If you’d like to talk, go for it—but you don’t owe him anything.

If my son were single, I’d tell him: Don’t do this. It’s a lazy shortcut. If you really want to meet her, go over, introduce yourself, and (here’s the magic) tell her you’d like to take her out on a proper date. Or, bonus points—remember her name, then find her on LinkedIn or social media. Send a polite connection request and let her decide if she’d like to know more. It’s 2025—social media is a tool, not a taboo. Refusing to use it is like insisting on a landline because “cell phones are a fad.”

The Dinner-Table Dilemma

Now, if I’m out having dinner—alone or with friends—and a man I’ve just met tries to pay for my meal, my answer is a firm, polite no. Here’s why:

When someone picks up your dinner tab before there’s any established connection, it changes the tone. It blurs the line between we met by chance and we’re on a date. It also risks sending the message that he’s leading with his wallet instead of his personality—and that’s not attractive to me. I’m looking for confidence, charm, intelligence, and a sense of fun—not a man who thinks the fastest way to my heart is through the check.

But What If He Beats You to It?

If someone pays your tab in advance and you find out after the fact? You still don’t owe them anything—not your time, not a conversation, not a dance. A quick thank-you if it feels right is plenty.

Knowing What Season You’re In

All of this boils down to knowing yourself and your intentions.

There have been seasons in my life when I was just out to have fun and maybe find a dance partner—and even then, I didn’t love strangers paying for my drinks. Right now? I’m dating with intention. I’m looking for the man I’ll wake up next to every morning, travel with, share the simple things in life with, and the deep and meaningful moments—the man who’s my partner in life and love. I’m not giving my time, energy, or heart to anyone who’s not aligned with that.

That’s the real “rule” here: be clear about what you want, and don’t compromise it for a free meal or a fancy drink. The right man will happily make the effort to ask you out properly—because he’ll want you to know you’re worth the effort.

🍯 Honey Note:

Real connection isn’t served on a silver tray with the bill tucked underneath—it’s built with conversation, play, and curiosity as the main course. If he’s the right man, he’ll want to earn the seat across from you, not just pay for it.

💋 Honey — still sipping my own mocktail until the right man earns the next toast.