Unexpectedly Enlightening: Life Skills Learned from My Sugar Baby

I have always been—according to my family, at least—the worst gift-giver in existence. We’re talking socks for my (ex) mother-in-law for Christmas. Gas station air fresheners for my dad’s birthday. A card that I didn’t realize was actually supposed to be for bereavement for my niece’s graduation (I mean, does it really matter what the card says as long as it’s filled with cash?)

Eventually, I just gave up. If someone actually wanted something from me, I told them, they could ask for my credit card number. But, I was not going to transform into some expert gift giver just because my family was tired of getting what they called thoughtless gifts for every special occasion.

And, to be fair, I made that clear in my sugar relationships, too. I was simply not going to be the kind of daddy who gave good surprise gifts. If my partner wanted to go shopping, I would happily tag along and catch up on work calls while she tried on every outfit in the store. If my partner wanted a specific designer bag, I would get her name on the waitlist and put a reminder in my calendar to go pick it up for her. But beyond that, I just didn’t understand the necessity for surprising a partner with a gift. There was just too much pressure, and it always felt like a test that I was bound to fail.

But, as you’ve probably guessed from the title of this, my experience changed when I met Kat. Kat has always been an excellent gift giver. As she explained it, gift-giving is her “love language," another thing that I knew nothing about before I met her. Apparently, that means that it brings her joy to give gifts. She even showed up to our first date with a gift: a bag of specialty coffee from her favorite place, because I had mentioned one time that I liked making my own coffee in the morning. We’re talking about that level of care and thoughtfulness.

Even so, I gave Kat my whole speech about not giving surprise gifts as part of my sugar arrangement. She could ask me specifically for what she wanted, and I would even have it wrapped real nice and delivered to her front door. But I was never going to be the kind of guy to pick something out that made me think of her and give it to her as a nice surprise.

Kat was kind of smiling secretively as I said all of this. She said that she didn’t need me to be a great gift-giver, but she would still want to give me gifts because it was something that she enjoyed. And as long as I was fine with that, she was happy to not receive anything that wasn’t explicitly included in our negotiation.

Over the next few months, things went about as smoothly as they tend to go in the beginning. There were a lot of getting-to-know-you questions and a little bit of awkwardness and a good amount of simply enjoying being together. One day, as we were walking through one of her favorite neighborhoods in the city, she stopped in front of a thrift store. I, personally, hate thrift stores. I think they smell like mold and despair. But I didn’t want to be away from Kat even for a few minutes, so I followed her inside.

She said that she wouldn’t take long, but that her sister had a birthday coming up, and she wanted to see if anything caught her eye. I asked her how she went about finding something in piles of junk like this and making it not feel like a gift that she pulled out of the trash (okay, my family has also said that I don’t have the best delivery when I’m sharing my opinions, either.)

Kat wasn’t offended. She said, “Okay, I’ll let you in on my process. When I’m looking to buy something for someone special, I’m looking for connections. I’m looking for things that either remind me of that person, or things that I know they would like, or something that loops back to a conversation we had or an inside joke.”

She stopped at a shelf filled with jewelry boxes.

“For example, my sister said to me the last time that I was at her house, that she keeps showing up to places late because she can’t find her matching earrings. So, a practical gift could be a jewelry box that has little compartments for her to separate her earrings.”

“Okay,” I said. “I get that. But then, how do you know which jewelry box she would like?” She took a moment to look over the different boxes, opening each one up and taking a look at the state of the inner lining, whether it had working hinges, etc. Once she had eliminated the majority that had too much wear & tear, she placed two boxes in front of me.

One was flowery and pink and played a song when it opened. It looked, to me, very feminine. The other one was more rustic, made of hand-carved wood and with an inner dark red velvet lining. I immediately pointed to the first option, thinking that any woman would probably prefer the more girly one.

“Hold on a minute, partner,” she said playfully. “I haven’t told you the most important information yet. My sister is not a girly girl. Everything in her apartment is dark wood and wool rugs and neutral colors.”

She placed the pink box back in its original position on the shelf and carried the wood box to the counter.

I was at once amazed and a little overwhelmed by the amount of care that went into Kat’s gift-giving process. I asked her if she ever got tired of it.

“No,” she said. “And the next time I see you, I’ll show you why.”

Our next date was after Kat’s sister’s birthday, and she showed me a video of her sister’s reaction to getting the gift. It was, I have to admit, pretty heart-warming to see how much her sister appreciated the jewelry box and understood the care that had gone into finding it.

And, I also have to admit, that it made me want to get that same reaction from Kat. I wanted to be the reason why she felt cared for and considered. And so, I started my new phase as an amateur gift-giver.

To be sure, my first few attempts were not great. I gave Kat a dog sweater for a dog that I didn’t realize wasn’t actually hers, but one that she had been pet-sitting. I gave her a coffee maker that she already had. I gave her a box of gourmet pears because she said that she ate a lot of fruits, only to find out that the one fruit she was allergic to was pears.

But one thing that I realized very early on was that, actually, the gift didn’t matter. Of course, yes, it did matter, and I was hell-bent on landing on a gift that she would love. But I realized that it really was the surprise and thrill of getting a gift that was the most fun.

Over time, as I learned more about Kat and her sense of taste and style, the gifts themselves got better. I was able to give her items that she truly wanted and didn’t feel compelled to pretend to like. She stopped saying that awful phrase, “it’s the thought that counts.”

And my family noticed the change in me, too. Christmases became a little more thoughtful. I rarely missed a birthday. When my niece graduated from her master’s program, I was able to give not only a graduation-appropriate card but also a physical gift (an espresso machine) that made her absolutely light up.

I never thought that I would become the gift guy, but here we are, and I couldn’t be happier.