The Perfect Fit

Posted on 2022.08.29

This Gentleman is an interesting fellow. He doesn’t live in the city but travels here often.

His routine is exactly the same: he books time with one of us on a Friday evening (always a Friday), takes us shopping for a few new outfits, takes us to dinner, and ends the night relatively early. We never go out with other people, and we are always asked to dress casually when we meet.

I know the people in the stores look at us funny. Not him. Us Companions. Everywhere we go he’s treated as a regular and all the staff all seem to be familiar with his routine. In one boutique, he simply points at the mannequin and asks us if we like the ensemble. If we do, we get the entire thing, except for the shoes.

For the shoes, we always start at one specific store. He loves the shoes we wear in our photos, and will often pick out a new pair of the same style for us to enjoy. Even though we know he wants us to wear the same shoes, he will have us try on a few pairs, “just to be sure”. The staff will bring us glasses of bubbly while we shop and he always declines (he doesn’t drink), but they go through the pretense of offering as they know it would be more rude to not offer him something. He will then ask for water and they’ll bring out an imported sparkling that they know he likes.

How do I know this happens on every date? Because almost every Companion has had the same one. It feels odd, but this Gentleman is always so gracious and polite that none of us want to spoil his fantasy of having this makeover be the first time for each Companion. It kind of feels like Pretty Woman but not, if that makes sense. You can tell how the staff in the store jostle for position because they know the commission will be a good one. I’ve enjoyed my dates with him because I’m never treated as well when I go in on my own.

He has us try on the outfits – with the shoes of course – and studies us as we model for him.

He asks about fit, and fabric, and whether or not we feel comfortable in the ensemble. I used to model and it almost feels like I’m at a fitting for a shoot or a show. He’s an engineer and the way he goes about analyzing the outfits makes me think that this is how he’d examine a bridge.

One time, I tugged on the hem of a really short dress and he vetoed the entire outfit, explaining that he wanted us to be as comfortable as possible. Once we agree on some outfits, he leaves it up to us to decide which one we will wear out for the evening. The rest – including the casual clothes and shoes we arrived at the store wearing – are carefully wrapped up and placed in bags. Everything is then carried out to the town car and we head to dinner and to enjoy the rest of our night.

The other part of all this that is kind of odd? All of this is within 90 minutes. From shoes to clothes to accessories to paying (and tipping!) the staff. Never late for the reservation. Perfect precision. It’s not often he repeats a date with a Companion, but I’ve been lucky enough to go out with him three times in the past year. I don’t even mean lucky because the dates begin with a wardrobe upgrade. It’s actually how he manages to make me feel during our time together. Like I said, I used to model and when you’re a model, you are often treated like, well, a piece of meat. If the clothing doesn’t fall just right, they say it’s because you got too fat, or too skinny, or you’re just the wrong shape. You’re studied like a specimen. Not with this Gentleman.

He studies to see if you like the outfit, and that you enjoy being in it. He never dresses us up like paper dolls, randomly throwing on pieces. We are adorned and he takes pride in how we look. The last time I saw him I asked why he didn’t ever purchase something for himself in any of these stores. He laughed and said that it’s more fun for him to watch us experience it than it is for him to shop. But, he admitted that he does visit his personal shopper on the Saturday to pick up a few items before he leaves town. Turns out that he doesn’t come into the city on Fridays, but that he’s actually been there the whole week, working. He then spends the weekend treating himself: time with a Companion to make “a beautiful woman even more beautiful”, then time for himself on the Saturday, a trip to the spa for a massage and haircut, and then back home on a Sunday night redeye.

He enjoys the structure and the routine and I suspect that he also enjoys having some control.

But again, he goes about it so respectfully that you come away from the encounter feeling good about yourself and him. If his fantasy is to engineer a perfect evening (and they always are), while being a perfect Gentleman, I’m happy to play the role as assigned. Wardrobe and all.


Photo by Unsplash

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