On Dating : This Time I Gave The Gift

On Dating : This Time I Gave The Gift

Sometime in January, 2019. 10:14PM Couch, San Diego

I’m generally monogamous. Once I sleep with a new person I usually stop talking to anyone else. There’s an assumption of exclusivity. You are sharing something deeply personal and trusting each other. Until that point, I am open to running multiple courses simultaneously to see what I like best.

I woke up with a text from Maddy. It was snowing in NYC and she sent a video. There was a loud truck blowing through the frame but it didn’t matter because she sent me something. 

I opened Instagram and saw that Erica was back from Paris. I messaged her, “Welcome back.”

Then Erica and I FaceTimed three times for ten minutes each between all of my meetings this morning. It was a bit of a joke by the end. She said it was good for us to take short breaks and it didn’t matter that we didn’t really have enough time to talk about anything.

I texted a bit with Maddy. I let her in on some of my day and how I was partnering with this commercial real estate guy for a project. She asked if I was excited and I said I was a little bit. And also that lately I have been thinking about crawling under the covers and not responding to the day because it feels like too much effort. It doesn’t feel like new year, new me but instead it feels more like 2019-2 and I’m tired. 

“For whatever it’s worth, I admire your tenacity and I’m sure you’ll be able to retire soon,” she texted. 

She admires my tenacity. She sees my tenacity. 

Maybe because I’ve nudged her to see what I want her to see by choosing certain conversations. 

In the morning, Erica and I talked about little things. She gave me a tour of her nice apartment in Brooklyn and even put on a jacket to take me to the roof deck. That’s always a selling point for New York people even though they probably use it four times in the course of a lease. 

I messaged Audrey back and told her she was funny and had me laughing. I elaborated on her message about whether or not bathroom graffiti artists carry markers around them with the intention of tagging something or if they spontaneously realize they have a marker when they’re on the toilet and feel struck by an inspiring idea that needs to be shared. 

She is a nurse and she looks just like Kate Beckinsale with the same smirk. 

My meetings came and went. FaceTiming with Erica came and went. Texting with Maddy came and went. She is my favorite still. I sent her a photo of my Birks and socks.

“Oh my god that just reminded me that I had a sex dream with you in it last night,” she responded.

“Was I wearing the Birks?”

“No, but that would’ve been an incredible psychic moment for you. All I remember is that we were in your bed and, needless to say, there was a lot of passion.” 

“I love a sex dream. Because you can feel it. Can you feel it in your body right now?”

“Oh, I feel it. And since it’s like we basically already did it I think I’m pretty much on board,” she said.

“I want to be in that bed with you right now,” I concluded with a lot of heat pressing into my skin.

Erica and I really only talk about superficial things. We make jokes about being rich and having a beach house. She likes my dimples and says my eyes are really blue. I ask her if maybe she’s only into the idea of me. It’s really hard to get to know her. And yet, we’re smiling the whole time.

LA Guy also FaceTimed Ashley this evening when we were all together. I nearly slapped the phone out of her hand when she thought about answering it. He has been less than consistent towards her and I don’t recommend making it easy for guys who are used to getting everything they want.

“You guys, what do I do?!?!?”

Michaela said to answer it and I shouted so loud no one else could be listened to.

“Put the goddamn phone down and just wait it out.”

Finally, she put the phone down.

Maddy’s package was arriving today. She lost her Airpods. She was very angry about it. I was going to buy her a new pair and realized that was incredibly aggressive so I found a pair of wired headphones from my last iPhone purchase and packed them in an envelope with a note.

I checked the 35 fucking digit tracking number and saw that it was delivered at 11:58AM. She was going to get it when she got home. When was she going to be home? 

The text came in after 6PM my time.




All caps. The millennial love call. She was touched. And she said as much. 

“Hi. Yes. Please don’t kill me,” I said. She was incredibly resistant to people doing nice things for her, like they couldn’t have possibly done them on purpose.

“I’m not going to kill you. I’m floored and want to die a little inside but the good kind.”

“Oh, okay. Great then. It’s also okay if you lose them. As the note states, no money was invested in this process,” I responded.

“I’m deeply touched and will try as hard as I can to treasure them but I’m also me and can’t rule out losing them immediately.”

She continued, “Oh and that’s a lie because you paid for shipping.”

“I put it on the business card.”

We felt the swirl. The punch of love that can only be given by another person when they think about you and do something nice and you think you’re no longer alone. 

I walked with Ashley later through our neighborhood.

We talked about Maddy. I was already starting to withdraw by then.

“I made a serious move,” I told her. “This could actually become a thing now.”

I live for that feeling. The crushing on each other. I gave her that on purpose. I knew what I was doing. That she was ready for an investment. Now I am worrying about how she might respond. If she opens up too much too quickly. If she says something vulnerable that asks too much of me. I’m fighting these thoughts. I want to be close. It’s okay to be close. I can open my heart that only knows extremes and try, for a second, to accept everything in between.

When I got home I went I through old drawers and found three letters from my ex-wife. She said I gave her hope and inspiration. She told me I was an enigma and the way I work so hard to provide for her and Woody and to be a better person was the most beautiful thing she’d ever been a part of.

That was also in the beginning. I had two tears. I didn’t end up being that person for her.

I texted her.

“You used to think I was so great. And then I became much less great. And I’m so sorry for that.” 

“It’s okay. I played a part in that less great stuff too.”

“I can’t emphasize this enough – you were an amazing partner and I was lucky to be with you.”

“Thank you for saying that. I hope you’re not beating yourself up today.”

There I was, with three different women in my orbit, texting my ex-wife and having her tell me not to beat myself up because I was feeling regret.

All of it was real and all of it was true. 

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