First Date Tips: Paying the Bill

by Tamar Caspi under Date Night,Online Dating,Single Life

You’ve made it! Another first date is coming to an end and yet the most uncomfortable part of the date has yet to occur: paying the bill. There are two scenarios depending upon how the date went:

Scenario 1
The date sucked. You know you don’t want a second date. The end of the date couldn’t come soon enough (even if things are “nice” you don’t want to waste anymore time) and finally the waiter brings the bill. You both reach for it. Your date is shocked that you’re reaching for it too. You offer to split. Your date is stunned. What do you say? Simply say: “I just think it’s right, but thank you for a nice evening.”

Scenario 2
The date went awesome! There was comfort, conversation, and chemistry! Neither of you wanted the night to end, but the restaurant was closing down and the night was late. The waiter brings you the bill, lays it on the table, and leaves. You both look at it because you don’t want this situation to become awkward when things have been going so great. Ideally, the man should take the bill and say, “It’s my pleasure to treat tonight and I hope there are more opportunities in the future for us to both treat each other.”

A couple extra tips:

  • Pick a restaurant where you know you’ll be able to cover the bill.
  • If you really want to impress your date, pull out all the stops and arrange to have the bill paid for before the check even arrives. Slip your credit card to the hostess or server whenever you get the chance.
  • If your date does pay, then you must make sure you express gratitude and don’t take it for granted.
  • If you’re going to make the motion to pay or split, then you better be able to follow through; don’t pretend to offer if you can’t back it up.


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Love at First JDate: Picking up the tab

by JenG under JDate,Single Life

I have gone broke from a first date more than once. Somehow, going on a date just extracts the paper bills from the inside of my pleather wallet without me realizing what’s happening. Once, a few months ago, going on a date even forced me to overdraw my bank account. Talking about who should pay for a first date should be on the list of topics for the next presidential debate (just kidding), as it warrants much emotion, opinions and even deal-breaking decisions by those who have rules and guidelines tattooed in their minds.

Here’s my breakdown on the payment plan for a first date—this one is targeted to the girls:

  • Do: Always offer to contribute on the first date. You both mutually decided to go out and “meet” each other on this awkward rendezvous and it’s only right you offer to shell out the cash for your half of the meal, or your gulp of a full glass of Pinot. You can follow your own rules on dates two through infinity. However, you should use your manners and offer to pay on the first round.
  • Don’t: Turn your shoulder on a first date who makes you pay. Yes, it’s lovely to be wined and dined on occasion, but it’s best to consider a first date with someone as a friendly meeting. A “let’s get to know each other—on a surface level and go from there” kind of thing. Don’t be upset or feel as though you’ve been stiffed.

Read more of Jen Glantz here.