How to make a woman feel comfortable with her top off

“So…um…how does one actually become a bra fitter?”

The question tends to be a stalling tactic, used by women clutching their shirts nervously to their chests as I enter the dressing room.

I learned to measure boobs by spending two full days undressed as a group of us, all new lingerie girls at a high-end department store, practiced sizing each other. But somehow describing any job training that involves nudity always seems a touch unsavory.

I maneuver the conversation back to the task at hand. I’m fairly certain I’ve come up with every variation of ‘can you please take your top off’ and yet the words still taste inappropriate.

You can tell a lot about a woman by the way she undresses. As a general rule, the older she is, the less self-conscious she’ll be.

70-year-olds shrug off their shirts and bounce around with their new bras on, just to give them each a proper go. Middle-aged women laugh at their bodies and make a cryptic joke about my youth. The new mothers always seem a bit confused by their newly sagging breasts and fresh stretch marks, and eye our nursing bra selection with all of the mourning of a ballerina throwing out her pointe shoes. Girls in their twenties blush, turn to the wall and keep their arms firmly crossed. With teenagers, there is always a decent chance of tears.

At the point of disrobing, most women feel obligated to point out their own perceived flaws, their tone apologetic:

“One of my boobs is larger than the other, I’m sorry it’s so weird…”

“I keep telling myself I’ll lose weight before I buy new bras but I’ve been trying for a few years now…”

“My nipples are so droopy—is there a bra that can fix that?”

I tell them that I’m past noticing this sort of thing. I’ve seen 38JJs, lactation in action, inverted nipples, augmentations, reductions, mastectomies, and pretty much anything else your top half can dish out. Now I just twirl my tape measurer and cut the self – critical diatribe off as quickly as possible.

As for me, boobs lost any semblance of sexuality after my first week on the job. They are now a bland as an elbow or an armpit.

I know the vulnerable moments aren’t actually when I’m with them, chatting away and throwing a variety of lace contraptions in their direction. The vulnerable moments are when they’re left topless in the dressing room with nothing to do but stare at their own bodies. Some women pull their clothes back on every time you run out for another bra, unable to be alone and naked with themselves for even a minute.

Conversely, the more her body has gone through, the less daunting a bra fitting seems. Cancer survivors never seem to give half a damn if their shirt is off or on. A young woman who had just undergone reconstruction after a double-mastectomy once bought the fifteen sexiest bras in the shop. An ancient-looking woman came in and demanded that I only find her bras in red. A woman who had recently lost half her body weight cried when I found her a cute, polka-dotted bra and it fit.

There’s not much you can do to make a woman like her reflection. You can measure her correctly, you can insist she tries on that one bra that’s just oh-too-sexy for her, and you can listen.

But at the end of the day, her sense of comfort, her confidence, has nothing to do with her body and everything to do with the way she looks at it.