How to Handle Awkward Money Situations at Restaurants


Most people don’t openly talk about money unless it’s a harmless conversation about how to save money on gas or your favorite personal finance software you’re using to manage your household budget. We’ve probably all encountered a few awkward money-related situations when we were forced to deal with some matter over money with a friend or family member. We don’t like to talk about it because maybe it reveals too much about our personal life, or we’re afraid what others might think.

So, how do you handle these types of situations? Here are three examples and some ideas of what to do when dealing with awkward money situations at a restaurant. These are just a few examples, so I’m interested in learning about your experience in the comments.

Splitting the Bill

Splitting the bill is sort of awkward for me for a couple of reasons. My portion of the bill might be larger, or visa versa. Also, I want to be fair in the situation and I certainly don’t want to end up paying more than I should, especially if it’s a big family dinner and we’re trying to control spending.

What do you do? In past situations I’ve been up front with the waiter or waitress as soon as we’re seated, letting them know who is in my party and that we’ll need a separate check. I think taking lead on this matter just makes it easier for everyone. But, I’m more open to splitting the check if it’s just me and a friend who I meet for lunch often. I think the money probably averages out overtime. At the same time, it’s okay for me if it doesn’t because they’re my friend.

The Other Party Insists on Paying

This situation has happened to me often and it’s usually with my parents. While I appreciate their generosity it can become somewhat awkward if they are always insisting they pay the bill.

What do you do? In these situations I’ve learned it’s okay to let mom and dad be my parents even though I’m a grown man with a family. I’ve done my best to pay and it’s just a hopeless cause. But this doesn’t mean I should expect them to pay. Each meal I assume I’ll be paying until told otherwise. To show my appreciation, I’ll sometimes purchase gift cards at a favorite restaurant and give them as a gift, or have even told them beforehand I’d like to take them to dinner. Sometimes they let me!

Calculating the Tip

Some parties like to ask the other party how much they plan to tip. My feeling is this is a personal matter and it’s a little awkward to share how much you plan to tip.

What do you do? When someone has asked me in the past how much I plan to tip, I’ve politely told them. It would be too awkward or rude for me to tell them it’s none of their business. Generally speaking, if it’s a large group at dinner and the waiter or waitress has done the minimum to serve us, I tip 20%. In fact, it’s not often I tip below this amount. I would say someone has to really do a poor job, or just not care to get anything less than 20%.  All this being said, I like this for a response: “I tipped 20%, but feel free to tip whatever amount you’re comfortable tipping.”

How have you handled these akward restaurant money situations? What other situations can you think of that have led to awkward feelings at the dinner table?

Photo by Marit & Toomas Hinnosaar

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  1. Dan W.

    Thanks, Jason! That’s a discreet way to splitting a bill. It makes splitting less awkward.

  2. Randy

    I always pick up the bill for my kids and their kids (ages 5 and under). This weekend, the kids will take me to dinner for my birthday and I’ll pick up the tab. (seems backward, doesn’t it). When I go with my mom, I pick up hers. If brothers/sisters are there, one of us will pay mom’s (we’re financially better suited to do this).

    I typically tip between 15%-20% based on the bill after tax. I calculate both values (or approximate) and find the nearest even $ amount between the two. If we have the kids with us, they made a mess, took a long time, or had exceptional service, I’ll round up and/or add a few $$ to the tip.

    My tipping habits improved when my kids were servers in restaurants.

  3. David Newby

    Nice post Jason. General question, what would you do in a situation if there’s a clear disparity between your financial situation and another person’s? If you’re better off financially, and they insist on paying the bill do you let them [although you feel like it would be a bit of a burden to them]? Vice versa, if you’re worse off financially than the other party, and it would be a bit of a burden for you to pay the bill [yet you want to save face and do it anyway out of kindness], would you still insist on paying. I encounter both situations from time to time.

    PS. there’s a great scene in the movie ‘Pursuit of Happyness’ where ‘Chris Gardner’ gave his last $5 to his boss, even though he really couldn’t afford it. Perfect example; great movie; check it out if you haven’t seen it–starring Will Smith and his son.

  4. Jon | Free Money Wisdom

    I use my handy dandy tip calculator on my phone these days, seems to work great. I set it at 20% and call it a day. It never seems to be awkward for me in terms of splitting the bill because a couple of us go out to eat once a week. it all averages out over time so we all throw in our credit cards typically.

  5. Jason Price

    Randy, thanks for sharing. I enjoyed reading your comment. I think your approach is a great way to show love and appreciation for your family. I’ll probably do the same one day for my kids. 🙂 Nice to hear your perspective on this situation.

    David, you bring up an excellent question. I don’t know that I have a great answer, but I think I would be honest, especially if the party was a close friend. You might show your appreciation and with a loving heart tell them to please not feel like they have to pay. If you know they’re in a rough spot financially and they have openly shared, you might lightly bring this up and let them know you’ll spare them any further financial burden. Anyway, I know there is a risk of offending, so it all depends on the relationship you have.

    Love your example of the movie. I did see it. I think we shouldn’t ever feel like we have to pay. No one is saying that. It’s a self imposed feeling or rule. Yes, I’ve been there too. But, let’s remember that God expects us to be faithful stewards, and in this case, the wise steward might choose not to pay.

    What do you think about these thoughts?

  6. Jonathan

    Interesting topic. I enjoyed all comments too. Randy, my Dad is the same way, and I suspect too that I am as well.

    My first job out of college was at a regional steakhouse chain and I became privy to tipping habits. Jason, I commend your 20% minimum general tip. I do remember though, when I was younger, the rule of thumb being 10%. Maybe that is just what my Dad told me because we didn’t have a lot of money , I don’t know. Then, I learned in high school and college that the tip amount was 15%. Now, I think it is creeping up to about 20%.

    If a waiter is getting $2.00 per person at a table, I have found, that is a pretty good tip for most casual resteraunts.