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Check, Mate! Who should pay for the first date?

Posted by Ali | Tuesday July 10, 2007 Leave a comment

This is an ongoing debate for the single set that probably won't end any time soon. We recently came across a blog post on this issue and it prompted us to write our own response. Luckily for you, we think we have it figured out. We’ll make it really simple:

LET THE DUDE PAY
It is in a man’s nature to enjoy the whole pursue and conquer thing. They like to woo you and eventually win you over. Having scored a date with your fabulousness, most men will also expect to pay for the date unless they are not that interested in you, or they are cheap. This has nothing to do with how much money you have or how you can support yourself, it is about basic pursue and conquer and making sure he realizes you know your worth.

The moment you whip out your wallet you risk sending the following messages:

I don’t think you can afford me.

I always pay my own way so if you’re cheap, I’m your lady!

You are the only date I’ve had recently and I don’t want you to feel obligated to pay for me. (i.e I don’t value myself that much)

It also automatically takes the romance out of the moment and makes the whole date feel very plutonic when either of you goes, “ok, so your half is $42.76…”

Having dated both men who pay and cheapskates who split the bill, or worse, made us pay for the whole thing, we’ve learned a few valuable lessons about this. Without fail, any guy that didn’t pay turned out to be a cheapskate to the core. On a second date, one guy invited me over to dinner, then proceeded to ask me to pay for 50% of the grocery bill. (!!!) And he was a Dentist. Imagine marrying that guy? “Honey, out of the 10 toilet paper rolls I bought this month, you used 6 of them so you owe me approximately…”

If he can’t afford to pay your way, he should arrange something like a romantic walk in the park with ice cream, a day at the beach or some other cheap or free activity. That kind of date can be very sweet and is far more romantic than taking you somewhere fancy where you have to foot the bill.

On the other hand, if YOU asked HIM out, it would make more sense for him not to feel obligated to shell out for the whole thing, and you should be prepared to pay.

The bill is on the table. Now what??
We realize not everyone feels comfortable sitting there expectantly when the check arrives, so here is how you handle it in the future.

If you are on your first or second date (or possibly the 3rd), just before the bill comes, excuse yourself to go to the bathroom. If it is still there when you return don’t even look at it. If he pushes the bill towards you, pay for yourself and then lose his number. If the bill comes while you are sitting there, just continue the discussion like normal, let him reach for it and deal with it, then sweetly say thank you (Guys HATE it when they pay and you don’t thank them for it) and trust that your company is enough for him to leave the date happy and hopefully ask you out again. Trust us, he won’t resent you because he paid for you. As the relationship progresses past the first couple of dates, you can start to chip in and pay for things where appropriate so he doesn't feel taken for granted.

One final note: Don’t even think about putting out just because he took you out. That is never a good reason and it will make him think you are cheap and lose respect for you. He will wonder if you sleep with every guy who buys you a burger. The longer you hold out, the more he will appreciate it when he finally gets it and the more he will value you.

What do you guys think?
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