To Pay or Not to Pay? That is the Question… by blogger Toni

You finished eating long ago. Your plates have already been cleared. You’re on the last sip of your last drink…

And then, it happens.

The theme music from Jaws starts playing in your head as you see your server walking back towards your table. As this internal background music builds to a peak, you can see it happening in slow motion: the check comes crashing down to the table smack dab in the middle of you and your date.

What do you do?!

Now, I don’t know about you, but I am unbelievably awkward when it comes to the dreaded “check please” moment on any first date. What circumstances or situations should I offer to pay? How can I make my offer to pay seem genuine? How many times should I insist on paying for myself before eventually conceding? Is it offensive to not even offer to pay?

If you find yourself stressing over these questions, trust me when I tell you that you are not alone.

Offering to pay for yourself is obviously always the polite thing to do. Is it wrong to expect him to pay? No, not necessarily. It’s a pretty well-known rule of dating that he is supposed to pay. And realistically, he should take care of it without hesitation… But in those early on dates, it can sometimes be hard to read the situation, which can end up making things a little awkward.

If he does immediately grab the check or pay for the tickets or whatever it is that you’re doing, then you should always respond to the gesture with a swift and genuine “thank you.” You don’t have to make a huge deal about it or anything, but you do definitely need to acknowledge this gentlemanly act of courtship.

If however, you’re unsure of whether or not he’s going to pay for you, it will never hurt to at least offer to take care of your half. The important thing to remember here is that you mean it when you’re offering to pay for yourself. That being said, more often than not (unless it is a horror story-esque first date) your male counterpart will be ready and willing to pay for you. It is crucial that you are always at least prepared to pay for yourself, but it is unlikely that you will be asked or expected to do so.

All in all, read the situation to the best of your ability and go from there. Your instincts will tell you whether or not you should be offering to pay (or even actually paying) for yourself. So try not to focus too much on this part of the night! Instead, try to focus your energy on enjoying yourself and seeing if there’s real potential with this new first date partner of yours!