Annie and I had been broken up for months before she invited me over to her new place. It felt a little ill-timed at first. Things had fizzled with a rebound. I thought at first that Annie wanted to go for a breakup victory lap. Gloat a little. But when she led me up the stairs to her new place, I noticed that she had worn the Agent Provocateur leggings and garter belts I had bought her for our first anniversary.

I was young. Didn’t know quite how to read this. Was it coincidence? Coincidence that this girl—whom I had seen dress each day with meticulous precision—had chosen to wear these leggings today? Was she meeting up with a new boyfriend later on? Were they for my benefit? I felt that curious turn-on between jealousy and anger.

But either way it was a vindication, I thought. But then I found myself wondering if she’d also worn the matching bra and panties. I found myself wondering that very, very much.

 

2006

“I want you to know right now that I think this is a bad idea.” My best friend Ben is standing next to me outside of Agent Provocateur. In my right hand, I have successfully—at 22—bought tasteful lingerie for an anniversary. But across the street I spied: A Chess Supply Shop. And they had the chess clock I was looking for.

“You’re looking at it the wrong way.”

“No I get it. When you guys have your all night ‘discussions’ you want to make sure you have equal time. Fine. Don’t get it as an anniversary gift. You’ll undermine everything we just went through.”
“That?” I said, turning back to the Agent Provocateur. Oh, that was nothing.

Was I being cocky? Meh. Mostly I was just being 22. I had experience with this.

 

1998

Michelle was in my older brother’s grade. When she came home from Dartmouth that Christmas, malls were booming. The underpants industry had exploded from the long-fetishized underground to Victoria’s Secret. What I liked most about this was, of course, the readily available catalog. Also, this meant that the lingerie section was no longer the most awkward entrance to walk into a department store with your mother.

Michelle’s neighbor came along with me. She had also done the recon of getting Michelle’s sister to tell us her bra size. In exchange for a pasta lunch and a ride to the mall, the neighbor entered Victoria’s Secret with me for the first time.

As I entered the door and smelled the perfume, I immediately recalled a terrified male friend whose last words to me were, “Aren’t you worried you’ll get a hard-on?”

Upon entering the store I had another worry: I feared I would never get another one again. Lingerie—that had entertained me every Sunday in the newspaper ads for Bradlees—now looked so lifeless on the bins. In school we’d heard tales of horny Japanese businessmen who bought girls’ panties in vending machines. I would probably get more turned on if they also sold Snickers.

That night, over IM, I discussed the matter with female acquaintances from youth group. I couldn’t believe women would wear these uncomfortable-looking things. In the end I got her a simple shelf-camisole (to wit: she was a size “M,” and now her younger sister, whom I would have to see in school each day, knew what a filthy pervert I was).

To make it worse, I forgot about the pink VS bag. Which my mother then found. She then broke character and said, “Dad and I are dying to know what you got Michelle at Victoria’s Secret.”

I think it disappointed her most of all.

That Christmas, Michelle called me up to see if I wanted to go with her family to see You’ve Got Mail. I rode in the minivan with the family. Still not certain how it went.

But on the way home she told her dad to park the car at their house. She would drive me home herself.

 

2002

Although it was unfashionable to declare so in college, Amanda declared herself an “underwear princess.” She would go on a camping trip with matching top and bottom, if need be. The devil be damned. I found this odd because she was small breasted, never wore makeup and dressed, as we all did in college, like someone whose clothing was chosen for them by the Red Cross.

When Amanda went abroad, I decided to give Victoria’s Secret another go. This time I knew her proportions. But when I walked in, it never occurred me that I would feel even worse as an adult buying underwear. In the middle of the store I discovered that Amanda was both of the smallest sizes they carried. As the words, “32aa and an extra-small bottom” came out of my mouth, I felt weird all over. The last time I bought underwear, I was sixteen. This time, I felt like a grown man getting something for a sixteen year old.

It was years before I could shake that off.

 

2006

Annie has just opened her anniversary presents and is crying in the living room. Text messaging exists. Ben is still begging me not to give her the chess clock. He says put it away. Pretend you found one and say, Wouldn’t it be cute if we…

That’s when Annie walks into the room in the complete Agent Provocateur. The stockings hang limp from her, like Hamlet’s when Ophelia realized he’d lost it. “I wanted to wear this for our anniversary night. But…but…I can’t get the leggings on?”

Perfect sizing on the bra and panties. I took a leap of faith to pick out her garter-belt size. But in the end, I was entirely out of my depth when it came to the leggings and went too small. (“Do you think I’m fat??”)

It should be obvious, but I had no idea you couldn’t return bottoms. Luckily, because I had gone with the garter belts, they were still exchangable and didn’t hang in the closet like an albatross.

 

2007

Annie has moved out and has taken the chess clock (which she adores) with her. I’m telling this story to my new girlfriend. Who is a lingerie designer. She laughs at younger Brendan. “Wait. But how come you never bought me knickers? I’d love to see what you picked out. It might help me with designs.”

Here’s what I learned: it really is the thought that counts. However, you have no control over what that thought is. Like most things in relationships, giving lingerie requires listening and caring.

I knew one thing, though: I didn’t want to give money to Nikki’s competitors so close to launch.

So the next day I tried one more time. I went to Target and got her a four-pack of some nice, but reasonably priced, silky blue underpants. I tell her, “When you come over to my house, I want you to feel at home. We can keep these at my place.”

“Are these from Target?” Nikki says. And then a single tear comes down here cheek. Nikki had interned at Target in college. They made her feel at home and homesick at the same time. Instead of trying to fix it, or return it, or upgrade, I just sat there with her while we had our little moment. It was the first time that I understood that giving lingerie is everything that lingerie should be: A bit daring, a bit sexy and quite a bit of fun.

Nikki’s lingerie line launched that Valentine’s Day. There was to be lots more lingerie in our future together.

But that four-pack kept us together through it all.