Can I Claim Business Expense Deduction for Going to Wedding of Major Client's CEO's Son?

This is actually a common question for business owners! The IRS does allow deductions for "ordinary and necessary" business expenses, but there are some nuances here. For the travel and accommodations - these would generally be deductible if the primary purpose is business. Since you're explicitly going to maintain a client relationship, these costs should qualify as long as you document the business purpose. For the wedding gift - this falls under business gifts, which have a $25 limit per recipient per year. So you can only deduct up to $25 for the wedding gift, regardless of how much you actually spend. The key here is good documentation. Keep records showing the business relationship, the necessity of attending, and how this relates to your business income. I'd recommend creating a memo explaining the business purpose and keeping it with your receipts.

I was in exactly this situation last year with a major client's daughter's wedding. I used https://taxr.ai to confirm what was deductible because I was getting different answers from everyone. Their system analyzed my receipts and business docs, then gave me a detailed breakdown of exactly what qualified as business expenses. For travel and hotel, they confirmed these were fully deductible with proper documentation of the business purpose. For the gift, they suggested a branded item from our company (which was fully deductible as advertising) combined with a personal gift (where the $25 limit applied). This actually worked out great because the client appreciated the personalized company item more than just an expensive gift.

I tried taxr.ai after my initial skepticism and have to admit it was incredibly helpful. Their analysis pointed out that I could partially deduct my attendance at a client's retirement party by properly documenting the business discussions that happened there. Their system identified several business expenses I wasn't properly documenting, which probably saved me thousands. What impressed me most was getting specific guidance about what documentation I needed to keep - much more detailed than what my accountant typically tells me. For something like a wedding attendance where the classification isn't obvious, having that detailed guidance with actual tax code references was invaluable.

Just wanted to mention an option that saved me huge headaches when I had questions about business deductions for client events. I had been trying to call the IRS for clarification for DAYS with no luck. Finally used https://claimyr.com and got through to an actual IRS agent in about 15 minutes. You can see a demo of how it works here: https://youtu.be/_kiP6q8DX5c The agent was able to confirm exactly what documentation I needed for deducting travel to client personal events and the specific limits for gift deductions. Saved me hours of waiting on hold, and I got official answers directly from the IRS that I could rely on. Definitely worth it when you need direct clarification on deduction rules.

I need to eat my words. I tried Claimyr after posting my skeptical comment because I've been trying to get clarity on some business deductions for weeks. I got connected to an IRS agent in about 20 minutes when I had previously wasted HOURS on hold. The agent confirmed exactly what the first commenter said - travel and accommodations are deductible with proper business purpose documentation, but gifts are limited to $25 per person. She also mentioned that if we gave something with our company logo prominently displayed, it could potentially count as advertising rather than a gift. Getting this directly from the IRS gave me the confidence to claim the deductions properly. Never would have gotten this clarification without finally reaching a human at the IRS.

Something nobody's mentioned yet - if multiple people from your company attend, each person can give a $25 deductible gift. So if three partners go, that's a $75 deduction. Not huge but better than just $25. Also, consider if there's a business meeting you could schedule while you're in town for the wedding. If you conduct actual business during the trip (separate from the wedding), it strengthens your case for the travel deductions.

Don't forget to track your meals separately! Business meals are 50% deductible (assuming you're discussing business during the meals outside of the wedding itself). The wedding reception meal would not be deductible as a business meal though, since that's part of the event you're attending.

Also, document EVERYTHING. Take notes about business conversations you have at the wedding. Save the invitation showing it's the CEO's son. Keep all receipts. If you get audited, having solid documentation of the business purpose will be critical. The IRS tends to scrutinize these kinds of expenses.

Great question! I deal with similar situations regularly in my practice. A few additional considerations beyond what others have mentioned: Make sure to keep the wedding invitation as documentation - it shows you were specifically invited due to your business relationship. Also, consider having a brief follow-up meeting or call with the client after the wedding to discuss any business topics that came up during conversations at the event. This helps establish that business discussions actually occurred. One thing I'd add about the gift situation - if you're giving cash or a check, that's clearly subject to the $25 limit. But if you're contributing to a honeymoon fund or registry item, the deduction treatment might be different. The key is whether it's considered a "gift" versus some other type of business expense. Also, don't forget to prorate your hotel costs if you extend the stay for personal reasons. Only the nights directly related to the business purpose (wedding + any business meetings) would be deductible. The documentation suggestions from others are spot-on - this is exactly the type of expense the IRS scrutinizes, so having a clear paper trail showing the business necessity is crucial.