Will my areolas ever match after one was reduced? What are my options? (Photo)

Dear StereoSushi,
it is hard to tell for sure without an examination. Based on your photos, it looks like surgical option is the best. If you are considering surgery, I would suggest you consult a board-certified plastic surgeon. Only after a thorough examination, you will get more information and recommendations.
Daniel Barrett, MDCertified, American Board of Plastic SurgeryMember, American Society of Plastic SurgeryMember, American Society of Aesthetic Plastic Surgery

If you are wanting to improve on asymmetry the best option based on your photo is an areola reduction. It is important to note that sometimes the areola can stretch after the procedure. I encourage you to visit with a board certified plastic surgeon near you for a consultation. Be sure to learn the pros and cons of the procedure so that you can make an educated decision.

All women have significant breast symmetry.
Often it’s better to leave good enough alone than to try to get them looking exactly the same.
Individuals who accept asymmetry as being normal typically end up being more content with their own body and surgical outcomes.
Those who focus or obsess over symmetry are never going to be pleased.
The human body is highly asymmetrical and most people don’t recognize this enough.
This is true for the face and body as well as all internal organs.
To make an assessment regarding the outcome of a plastic surgery procedure we generally need to see proper before and after pictures.
I don’t see how fat transfer is going to make your areola larger.
This attempt makes little sense. Areola reduction is complex and unpredictable, especially when done unilaterally.
Is this really worth having more surgery for?
Mats Hagstrom, MD