I Got This: Who’s Picking up the Tab?

Posted on

Update to this blog:  The professional I mention in the next paragraph read this article, reached out and wrote probably one of the most eloquent emails I’ve ever read to explain her side of this transaction.  My mistake.  I heard her wrong.  She had said “Were you done, or….”  as opposed to what I heard… either way, I’ve invited her to lunch; my treat.  I probably would have gone ballistic and said some awful things if someone wrote what I wrote.  People surprise me every day.  It’s why I love them.

tab business womanI had lunch a with a woman that was trying to sell me her company’s product. We met, we ate and I didn’t purchase.  The bill arrived and the server asked her “all on one, or separate tabs?”.  She looked at me and said “were you going to get this or…” and in that 2 seconds I immediately determined that I wanted nothing to do with her. The tone of our last 5 minutes went from being delightful and hopeful, to me looking around the room for the bathroom and exit.  She knew it, I knew it and I will toss her card to the side.  I’m not sure if her demeanor changed because I didn’t pay or if she knew that I knew.  One thing was clear.  I didn’t care.  As a married man trying to run a business, it’s a waste of my money to buy lunch for a hot young executive just because she’s used to men buying her lunch.

We went out to an expensive dinner with some friends about 6 years ago.  We ran about 15 minutes late and see that everyone has drinks, appetizers and a couple of bottles of wine open.  Courtney and I order our own drinks, order one steak to split and choose not to get desert.  It should have been about $100 with tip for the two of us, but when the bill game, the other parties said “wanna just split it up?”… well shit… you can’t look like an asshole at that point, so we went with it…. $250.  It negatively affected our view of our friends and cost us much more than we could afford at the time.

I have a friend that picked up every tab because he became successful quicker than the rest of us. He wanted to go out with his friends to places he knew we couldn’t afford, so he just paid for us.  One day he was out with all of us and after a long night of drinking, the bill came and he said “don’t expect for me to pick this up assholes.”.  Fortunately, half of us prepared to pay and we would order accordingly, but you should have seen the looks on the rest of their faces.  People had to go to ATMS, borrow money and even ask a few of us to just pick it up.  That night will always stick out in my mind.

My best friend and I have a running tab that can swing into the 1000’s of dollars depending on where we are in our lives.  We’ve always tried to keep everything separate and on a running total just to make life easier unless we are making it clear that this is a ‘gift’.  It’s a system that really never fails but you can only do it with one person at a time.

So, how to avoid the awkwardness of the bill?

Set Expectations – Take ownership, take control.  If you are setting up any type of meeting, date or event at a location that costs money (restaurant, movie, bowling alley…), be clear with your intentions.  If you intend to pay for the evening, say something like “I’d like to treat you to a dinner” or “I’d like to buy you lunch”.  The other party is put at ease because they can either accept your gift as is or counter offer by saying something like “I’d like to meet you for lunch, but you don’t need to buy it for me.”  Be careful in a counteroffer.  You have to clarify immediately by saying something like “Let me buy this one and you can get the next one”.  Or you can say “That sounds fine if you’re more comfortable to split lunch.  When can we meet?”

Social Norms – There are assumptions that we make when it comes to setting appointments at bars, restaurants or other spending locations.

  • Initiators – Generally speaking, if you are the initiator of the meeting and recommend the location, it is assumed that you are going to pick up the tab.  If you are comfortable with that, I still recommend telling the individual or group you intend to buy, but it’s okay to set the meeting and let them assume.  If your intention goes against the norm, you can politely say “I’d like to get everyone together at Chili’s after work for a few drinks.  I figure this is a good place that’s also affordable for everyone.  I hope to see you at 7.” Make sure the meeting isn’t mandatory.  If it is, pay the tab.
  • Battle of the Sex – Sorry men.  Women are treated equal except for when they aren’t.  If tab madyou’re on a date with a woman, it’s expected for you to pick up the tab.  You have to be extremely clear of two things when you are one on one with a woman.  #1.  Is this a date?  Use that word when planning it.  “I look forward to our date.”  #2.  If you do not wish to pay for all of the date, but it is a date, say something like “If you’re like me, I’m on a budget.   Is Maggianos okay for you?”  Be careful.  #2 can come across as cheap.  Men, pay for your dates and make sure your dates know they are on a date.  You want sex, they could care less… buy them some dinner.
  • Authority – If you are asking to meet as a boss, you need to pick up the tab.  It’s assumed you are their boss and regardless of what your personal relationship is with individuals, they are likely attending because their boss asked them to.  If you do not intend to pay, be very clear of it up front.
  • Solicitation – If you are soliciting someone’s business or time, you are expected to pay the tab.  You should be purchasing them lunch if your goal is to get them to spend money.  If the meeting might be more of a joint show and tell, be clear that you choose a location that is “within each other’s budget”.  Sometimes meeting for a coffee is a cheap way to pick up the tab and keep the higher status.

tab moneyFriends – The most awkward bill scenarios comes when you are on a couples date with just one other couple.  The bill is usually not so large that you couldn’t afford to pick it up and both parties know it.  The chess match begins.  The check hits the table and eyes begin to shift.  Who’s looking at the tab? Who’s looking for an exit?  Who’s ignoring the tab completely? If I reach for it, will someone offer to pay it too?  Who initiated the date?  Should I be forceful in paying the tab?  Is that rude?  It can be awkward and quickly.  The truth is, if you are out with newer friends, you should just be clear up front.  “Let’s go out this weekend.  My wife and I like XYZ theatre and ABC for dinner. Let me know if that’s outside your budget for what you want to spend.”  This initial conversation can have the side effect of making the other couple feel “cheap” or lessor if they really don’t want to spend that kind of money, but there’s really no comfortable way to talk about money and this seems to be the most comfortable way by setting expectations.

Stop Assuming – My dad always picks up the tab.  I’m 33 and he just won’t let me pay.  I try… most of the time… unless he’s made it clear ahead of time.  That being said, I offer to at least pay my share of a tab.  Never assume that someone is paying your bill unless they have stated it.  Ladies, it goes a really long way if you offer to pay a tab.  Most of the time, the male will shut you down and pay it.  However, if they let you pay, especially on a first date, it may be expensive that night, but may save you the emotional expense of figuring out who they really are in the long run.  Think about it.  No matter what situation you are in, always order as though you will be paying your way.  Always have the means to pay.  If you are invited out and can’t afford the venue, but you think there is a chance someone will pay for you, just say “I would love to, but I can’t spend the money”… let the other person make the offer.


  1. Decide ahead of time what YOU want to do.  If you are prepared to pick up the entire tab, do nothing.  You can announce you’re paying at anytime you like.  If you want to make sure the tab doesn’t get ridiculous, don’t tell them until the bill comes.  Also, don’t be surprised if people already assumed you were paying and drink like fish.
  2. If you are comfortable with everyone paying the same % of the bill even if you haven’t had as much as everyone else, you’re still safe.  Just be clear you aren’t paying for the whole thing ahead of time if you were the organizer.
  3. There is no problem with asking for separate checks the first time the server comes to your tabletab waiter.  This will actually put everyone at ease, including the server.  It is super annoying to go back and itemize after the fact.  It’s acceptable up front, but can look “cheap” if you ask for separate checks at the end.  Some people might have assumed another arrangement and ordered accordingly.  Again, if you were the organizer, if you ask for separate checks up front, everyone is able to order at their own comfort level and enjoy themselves.  It’s really better to mention this before arriving to the event, but this works too.
  4. Don’t be frustrated by others.  Not everyone understands social norms. Some people make assumptions based on life experiences that don’t match yours.  The more you communicate, the less people will “let you down”.  22 year olds are going to “leech” more than 45 year olds because they just don’t know any better.  Young people expect old people to pay for shit.  Women expect men to pay for stuff.  Employees expect bosses to pay for stuff.  Kids expect parents to pay for stuff.  Poor people expect for rich people to buy.  It’s just how it is.   Be clear.

I’m not sure if there was any real humor in the column this week, but I thought it might be helpful to you.  If you made it this far, and you’re the first person to react, simply leave a comment on the blog’s facebook status that you read it and you like cheese and I’ll send you a Sick Puppies Comedy T-shirt.

Have a great week everyone.



Leave a Reply

Fill in your details below or click an icon to log in:

WordPress.com Logo

You are commenting using your WordPress.com account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s