2 doctors weighed in:

How do I tell new lady that I have to wear a bra because I have male breast enlargement?

2 doctors weighed in
Dr. Ed Friedlander
Pathology
1 doctor agrees

In brief: Tell the truth

Real gynecomastia (male breast enlargement) is easy to treat surgically.
Most men who have it would prefer to be rid of it, but some men love it. Some overweight men have fat that simulates breasts ("pseudogynecomastia"); most men with this don't like it and it can be removed by liposuction. Before the shirt comes off, tell her -- she may like it, or like you for who you are and ignore it.

In brief: Tell the truth

Real gynecomastia (male breast enlargement) is easy to treat surgically.
Most men who have it would prefer to be rid of it, but some men love it. Some overweight men have fat that simulates breasts ("pseudogynecomastia"); most men with this don't like it and it can be removed by liposuction. Before the shirt comes off, tell her -- she may like it, or like you for who you are and ignore it.
Dr. Ed Friedlander
Dr. Ed Friedlander
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