Dating Rules: Who Should Pay and When

  • Posted on: February 19th, 2009 by


This is a fantastic dating article that has honest dating tips and relationship advice about dating and money…

… Which at times can be a very touchy subject (shameless plug) and I just so happen to be quoted below.

Judy it’s always my pleasure to give you input.

By Judy McGuire

(The Frisky) — It seems that all anyone is talking about lately is the economy, so why is money still such a tough topic to discuss with your nearest and dearest? They say married couples fight over money more than anything else, but what about when you just started dating? That’s possibly even more awkward.

Columnist says no woman should leave her house on first date without enough money to pay for her meal.

The first date
Though Dr. Phil feels otherwise, my take on this has always been he (or she) who asks, pays. (The bloviating shrink says men should always be the ones to pony up.)

And if you don’t pay for the whole thing, you should at least offer to split the tab. Incredibly (to me), most women I spoke to thought I was an idiot and firmly believed the dude should always pay on a first date — though for some this was a recent change of heart.

Kate, a 33-year-old writer told me, “I tend to try to pay for myself, but as I get older and more comfortable with my awesomeness, I kind of wish and hope that the other person will be a little more old-fashioned about it.” Good point. If someone’s eating opposite Amazing Me, shouldn’t she or he pay for the privilege? After all, I’m entertaining and cute and if you let me order dessert there may be some smooching in your future.

Regardless of your feelings on the matter, whatever you do, don’t leave the house without enough money to pay for at least your share. It’s a first date so while he may seem great (and generous) on paper, you never really know what you’re getting into until he’s sitting across from you. Sure, he might be staring adoringly deep into your eyes, but then again, his pants might be held up with duct tape. Do you really want to count on that dude to know the meaning of “gratuity?”

What to say: “That’s so generous of you — can I at least leave the tip?”
What not to say: “This princess doesn’t pay for food!”

Dates two-thru-six
Jennifer Kelton, CEO and founder of, has built a business on bad dating behavior. She explains her thoughts on the money issue: “While it’s not expected, Let’s face it — we are hardwired to want the man to ‘bring back dinner to the cave.'” Up until my current relationship, I’ve almost always been in the driver’s seat finance-wise (and believe me, that’s a pretty meager seat) so I’ve always furnished my own cave.

I ask her if it’s okay to date a guy just for a free ride or free grub? Kelton says no. “Being cheap is never attractive and I would say that after more than four dates the woman should pay the tip.” Whoa! Just the tip? Apparently the women who called me a moron were onto something!

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About Jennifer

Jennifer Kelton

Jennifer Kelton CEO / founder LLC is a Los Angeles native and a pioneer in the worldwide dating industry, investigating the game of love while providing encouragement and support since 2007, starting with the acclaimed dating book Don’t Use My Sweater like a Towel. An accomplished CEO, visionary and entrepreneur, Kelton’s work in the […]

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