Sweet Tax Tips for Valentine's Day

Jeremy Springer
18 hours ago
3 min read

Envelope with "Sweet Tax Tips" card on green background, surrounded by hearts. Valentine's stamps read "To: My Valentine Special Delivery."

1) Pick the filing status that truly “matches” you

Your filing status affects your standard deduction, credits, and tax bracket. Use the IRS tool if more than one status could apply (e.g., Single vs. Head of Household). (IRS)

2) Give your paycheck a “withholding check-in”

A quick tune-up with the IRS Tax Withholding Estimator helps avoid both surprise balances due and oversized refunds. Re-check after life changes (marriage, new job, new baby). (IRS)

3) Don’t “double-book” dependents

Only one return can claim a dependent (with rare exceptions). Confirm who qualifies before filing—this also impacts credits like the Child Tax Credit and EITC. (IRS)

4) “Pair” the right education credit with the right student

You may claim both the American Opportunity Tax Credit and the Lifetime Learning Credit on the same return—but not for the same student or the same expenses. No double-dipping. (IRS)

5) Show future-you some love: fund IRAs on time

You generally can make IRA contributions for the prior tax year up to the filing deadline (not including extensions). Know the rules for Traditional vs. Roth and deductibility. (IRS)

6) Know your medical “love language”: HSA vs. FSA

HSAs, FSAs, and HRAs have different funding and reimbursement rules. HSAs can carry over indefinitely; FSAs are often “use-it-or-lose-it” (employer plan rules vary). Keep receipts. (IRS)

7) Standard deduction or itemize—choose the sweeter deal

Itemize only if your total allowable deductions exceed the standard deduction (or if you’re required to itemize). Consider “bunching” charitable gifts or medical expenses in one year. (IRS)

8) Charitable gifts: get the right “love note”

Donations of $250 or more require a contemporaneous written acknowledgment from the charity, and non-cash gifts have special valuation rules. Save those letters. (IRS)

9) Side-gigs and tips: don’t ghost your quarterly taxes

Income without withholding (gig work, interest, dividends, rents) may require estimated tax payments during the year to avoid penalties. Track every dollar and expense. (IRS)

10) Home office: only if you’re truly “exclusive”

The home-office deduction is not available to W-2 employees. It can apply to self-employed taxpayers who meet the “regular and exclusive use” test; a simplified method may be available. (IRS)

11) Investments: beware wash-sale heartbreak

Selling at a loss and buying a substantially identical security within 30 days can disallow the loss (it’s added to the new basis). Review reporting rules on 1099-B and cost basis. (IRS)

12) Marketplace health insurance: reconcile the Premium Tax Credit

If you got advance payments (Form 1095-A), you must file Form 8962 to reconcile or your refund can be delayed. Keep 1095-A handy. (IRS)

13) Want your refund faster? “Direct-deposit it”

E-file plus direct deposit is typically the fastest path; then track progress with Where’s My Refund? on IRS.gov (or IRS2Go). (IRS)

14) Protect your identity with an IP PIN

An Identity Protection PIN helps stop fraudulent returns filed in your name. You can request one (and retrieve it each year) via your IRS Online Account. (IRS)

Bonus Tax Tip: Set up your IRS Online Account

Think of it as a secure “digital shoebox”: view balances, payment history, certain notices, and tax records/transcripts. It also streamlines getting an IP PIN and verifying prior-year AGI. Enable multi-factor authentication. (IRS)

Legal Disclaimer: This post contains general information for taxpayers and should not be relied upon as the only source of authority. Taxpayers should seek professional tax advice for more information. This information was current at time of posting; we are not responsible for updating this or any blog post/article for subsequent changes in the law or its interpretation.