Yes, I would. The one with the gain must file. The one with the loss should file if you want be able to carry the loss forward to offset future income. It must be carried forward each year without skipping a year or it will be forfeited.
I you are using the online version, you might want to use the Freedom Project for that - it supports all forms.
You might be able to use the Freedom Edition for incomes under $33,000 and supports all states and most forms.
The Freedom Edition is part of the IRS Free File alliance and is totally separate from TurboTax website.
https://ttlc.intuit.com/replies/3301359
How do I switch to TurboTax Freedom Edition?
https://ttlc.intuit.com/replies/3491786
**Disclaimer: This post is for discussion purposes only and is NOT tax advice. The author takes no responsibility for the accuracy of any information in this post.**
