Going from single filer to joint filer this year, trying to time my stock sales correctly

REDDIT.COMMar 19, 7:07 PM UTC

Key insights

  • An individual investor is considering selling appreciated stock positions before getting married to take advantage of lower single-filer tax brackets for long-term capital gains. The combined income post-marriage will likely push them into a higher tax bracket. The decision hinges on comparing potential tax liabilities under both filing statuses. While the investor suspects pre-wedding sales are advantageous, the complexity warrants professional tax advice.
Going from single filer to joint filer this year, trying to time my stock sales correctly

Seven years of mostly index funds but also some individual stocks I have been holding long term. Some positions have appreciated significantly and I have been pretty careful about managing when I sell to stay within the 0% long term capital gains bracket.

Getting married in September. My fiance also works and has a solid income. Combined we are going to be in a completely different tax situation than I have been managing as a single filer and I am realizing I need to think about this before the wedding not after.

Specifically trying to understand if it makes sense to sell some of my appreciated positions before the wedding while I am still filing single or if waiting and filing jointly changes the math in a way I am not accounting for. My income alone keeps me just under the threshold for 0% long term capital gains. Combined income is going to push us well past it.

Ran some rough numbers and it looks like selling before the wedding might save a meaningful amount but I want to make sure I am not missing something obvious before I make any moves.

Is this something a regular CPA can help with or do I need someone who specifically understands this situation?

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