The Valentines Day Lesson

Some lessons can only be learned the hard way...

In preparing for this past Valentines day, I set up the plans for an evening out and for taking care of the kids. And I had a novel idea... I told my DW that I would take her out for a nice dinner - if I could dress her. I was planning a relaxed romantic Valentines evening of drinks and dinner at a traditionally favorite spot. I was thinking of her being in something sexier and more daring than usual. Something she wouldn't wear to work. Something she wasn't likely to wear out with just friends. Special. Nothing outrageous, but definitely something more form fitting and showy than the bulky comfy stuff she normally wears. And maybe even more sexy than her "little black dress".

The first lesson was discovering that there are just way too many women's clothing stores. And styles of clothes. And this quickly made the challenge of dressing DW daunting. Where a guy might have different colors of 3 or 4 different kinds of underwear, women have different colors of a myriad of shapes, fabrics, and styles of all sorts of underwear. And shirts, and skirts, and pants, and many things I still can't remember the names of... I would boldly enter the stores, and often emerge feeling like I had just had some mind-boggling other-world experience. But I persisted and learned...

They use strange words. They were very friendly and tried to be helpful. I would be looking at some items on a rack and would be asked if I needed help. "What would a woman normally wear with this" I might ask. "Oh, a schnoopleskirt or a nuffablouse" would come the answer. Occasionally I did recognize some words, like camisole. "But isn't that lingerie?".... "Oh, there are different types". Go figure...

When I saw things on a hanger or mannequin, it was hard to visualize them on DW who was not there. So I looked around the stores and malls. And I watched for women wearing similar stuff. Honestly, I wasn't oggling the women, I was trying to figure out how some of those nuffablouses would look on DW. By this time a dress was out of the question...

Things don't turn out the way they look on models or mannequins. More on this later...

So, after visiting ~30 clothing stores, and getting closer to the day, I bought a collection of garments. I got undergarments in her size. The bra and panties were from a lingerie shop. Not your normal bra and something you would not wear under a see through top. But it was shown as being for lower cut tops or dresses where the bra needs to be out of the way but still do its job. Then I got a very nice woven silk top. Very soft and pleasing to the touch and stretchy. A good opening in the front, but not too far. Still being a colder time of year I decided to get another layer that was soft, warm, and form fitting. I got a cashmere wrap-around to go with the top. And I got a skirt in her size. A soft pressed wool that went down to about the knee. For shoes and other stuff I relied on her current collection.

OK, so the evening came. The bra was the right size, but didn't fit quite as expected. But it wasn't bad either... The silk top was very nice and the wrap looked very good with it. The top was a bit looser than I expected, but was a decent fit. The cashmere wrap-around was a bit awkward at the overlap. The skirt was too big and got set aside for a nice pair of slacks... Oh well.

All things considered, I thought DW looked stunning. Tastefully sexy! Everything went together well, and although she was showing almost as much cleavage as she did in her wedding dress, and although you could see some of the bra if you looked down the middle of her top, it was tastefully sexy.

But during the evening it became evident that she was somewhat uncomfortable with it when she kept trying to adjust the wrap and any compliment was questioned. It becomes incredibly hard to compliment someone when they question the compliment or don't take it as such...

We did have a drink, a relaxed evening and then a very nice Valentines dinner.

A day later ... I heard all about how uncomfortable she felt in the outfit. How she felt on display, cheap, humiliated... Questioning my motives ... my intelligence... And so we learn...

Next time...
It is much better to fit someone for something sexy when they are there. And as a bonus, they can interpret the lingo for you.
It is hard for someone to feel sexy if they don't feel comfortable with what they're wearing (fit, style, or exposure). Surprises aren't the best way of doing this...

While the adventure of dressing DW still seems a good one, using never-before-worn garments got me in trouble...