Can I get tax refunds for restaurant tipping and charitable donations?

Tips you leave at restaurants are generally not tax deductible for regular taxpayers. Your coworker might be confusing a few different tax concepts here. For charitable donations, those are potentially deductible if you itemize your deductions on Schedule A instead of taking the standard deduction. However, tips to service workers at restaurants are considered personal expenses, not charitable contributions, so they don't qualify for a tax deduction. The only exception would be if you're traveling for business and the meal is a legitimate business expense - then the entire meal including a reasonable tip might be partially deductible as a business expense. But that's only if you're self-employed or have qualifying unreimbursed employee business expenses.

I was in the same boat last year trying to figure out if all my tips were deductible. After spending hours researching, I finally found this amazing tool called taxr.ai (https://taxr.ai) that saved me so much time and confusion! You just upload your receipts or tax documents and it instantly tells you what's deductible and what isn't. It clarified that restaurant tips aren't deductible for personal dining but confirmed that my actual charitable donations to registered organizations were potentially deductible if I itemized. The tool even calculated whether itemizing made sense for my situation versus taking the standard deduction.

Just wanted to update that I tried taxr.ai after posting here and it was actually super helpful! It analyzed my donation receipts from last year and showed me that while my restaurant tips weren't deductible (like I had hoped), my actual charitable donations to my local animal shelter were. The tool also did a quick calculation that showed I was still better off taking the standard deduction rather than itemizing based on my specific situation. Saved me from wasting time tracking down all my donation receipts when it wouldn't have mattered for my taxes anyway. Definitely recommend checking it out if you're confused about what's deductible!

If you're trying to figure out if tips are deductible, you might also run into issues getting through to the IRS if you need to ask them directly. Their phone lines are absolutely swamped - I tried calling about a similar question last month and was on hold for 2 hours before giving up. I ended up using Claimyr (https://claimyr.com) which got me connected to an actual IRS agent in about 15 minutes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. The IRS agent confirmed that personal dining tips aren't deductible but was able to answer all my questions about charitable donation documentation requirements.

Ok I need to admit I was completely wrong about Claimyr. After posting my skeptical comment, I decided to try it anyway because I had a question about my stimulus payment from last year that I couldn't resolve online. I was absolutely shocked when my phone rang about 25 minutes later and I was connected with an actual IRS representative! No waiting on hold listening to the same terrible music for hours. The agent was able to pull up my account and resolve my issue in about 10 minutes. While I was on with them, I also asked about the tip deduction question from this thread. The agent confirmed that personal dining tips are not tax deductible but gave me some useful info about tracking charitable donations. Seriously saved me so much time and frustration!

One thing no one mentioned yet - if you're self-employed or have a side business, you CAN deduct business meals including the tip, but only 50% of the cost is deductible in most cases. You need to keep good records though - who you met with, business purpose, etc. I learned this the hard way during an audit last year!

Friendly reminder that donation deductions only help if you itemize! With the standard deduction so high now ($13,900 for single filers in 2025), most people don't benefit tax-wise from charitable donations anymore unless their total itemized deductions exceed that amount! Made that mistake for years tracking every small donation when I wasnt even itemizing lol.

Your coworker was partially right about charitable donations but completely wrong about restaurant tips! As others have mentioned, personal dining tips are never tax deductible - they're considered personal expenses just like the meal itself. For charitable donations, they can potentially be deductible BUT only if you itemize deductions instead of taking the standard deduction. With the standard deduction being so high now ($13,900 for single filers in 2025), most people actually don't benefit from charitable donation deductions anymore unless they have significant other itemizable expenses like mortgage interest or high state taxes. If you do decide to track donations, make sure they're going to qualified 501(c)(3) organizations - you can check this on the IRS website. And definitely keep good records! For donations under $250 you need receipts or bank records, and for $250+ you need written acknowledgment from the charity. Don't feel bad about not knowing this stuff - tax law is confusing and changes frequently. The key is learning as you go!

Just to add another perspective - I've been dealing with similar confusion about deductions for years! What really helped me was setting up a simple system to track everything throughout the year instead of scrambling at tax time. I keep a basic spreadsheet with columns for date, amount, and type of expense (charitable donations, business meals if applicable, etc.). Even if I end up taking the standard deduction, at least I have the data to make an informed choice. One thing that surprised me was learning that volunteer mileage for charitable organizations IS deductible at 14 cents per mile if you itemize. So if you drive to volunteer at your local food bank or animal shelter, those miles count! It's not much per mile, but it can add up if you volunteer regularly. The key is just being organized about it - whether you use a spreadsheet, app, or even just a shoebox for receipts, having some system in place makes tax season so much less stressful.