A Modest Proposal, Part 3: The Dark Ages

In our last episode, Jill had just left my apartment to catch her train back to DC, and after she was gone, I decided that it was time to stop waiting for chance to bring her back to NYC. I wanted to see her regularly, really begin dating, and so I plotted how to make that happen.

I started by looking up flower stores in DC, and that afternoon I ordered flowers delivered to her office for Tuesday, along with a note thanking her for coming to the dinner party and saying how much I'd enjoyed seeing her. Can't go wrong sending flowers, I figured.

Two things happened on Tuesday.. First, I got an email from Jill thanking me for the flowers and telling me how surprised she'd been to receive them, how pretty they looked, and how much inquisitive attention they were generating from her co-workers. The second thing that happened is that I came home to find that a package had come from Crate & Barrel. When I opened it, I saw that it was from Jill, and that she had sent me... [an egg separator]. Until that moment, I'd completely forgotten our little exchange about egg separating, probably owing to the fact that I had been at least 40-50 sheets to the wind at the time it took place, but the moment I saw the egg separator, it suddenly all came back. (See part 2 for a recap). It came with an impish note from Jill, and I laughed and laughed.

In that moment, I remember thinking: "If we have just one more date, I think we'll end up married to each other." Since Jill had thus far done all the traveling, I decided to offer to come down to DC, with a secret agenda of asking to see Jill on a more regular basis. And to test that theory, about one more date.

And that's when the Dark Ages began.

In retrospect, I think they actually began before the dinner party; Jill had a certain... distance to her that night and the next day that I hadn't felt before. But we'd still had a great time together and so I'd overlooked that. But when followed over the next almost-a-month was a strange dance of trying to find a time to connect via the phone, having a hard time doing that, agreeing on a time only to have it fall through at the last minute, etc. It was hard not to come to the conclusion that what was happening was the soft landing, the no-without-saying-no to a question (are you really interested in me?) that I hadn't even had the chance to ask yet. But I had never felt so strongly so early for a woman before, and I didn't want to just let it fizzle, so I hung in there and we did eventually speak.

In that conversation, Jill told me that she'd been offered the job in Mayor Bloomberg's office, but that she'd turned it down. She said she had too much going on at her current job to leave it now, and also that it didn't work in her personal life to make that kind of life change at this moment. Although privately disappointed, I expressed support for her decision and then made my pitch to come and see Jill in DC.

After some negotiation, Jill said she could do it in early December, on a weekend when it also happened that her best friend Chris was going to be in town, so as long as I didn't mind that Chris would be there too, I was welcome to come. Now, that seemed pretty suspiciously like the weekend one would pick if one wanted a buffer there, but under the half-a-loaf-is-better-than-no-loaf philosophy, I accepted.

Thus, a few weeks later I found myself on a plane to DC. I figured we would go out that night with Chris and some other friends, but that eventually I would have at least a few minutes alone, so I'd rehearsed a little speech in my head and was ready to go.

We had dinner that night with Chris, and then went out for drinks later with Jill's friend [Alison]. We had a very nice time- I enjoyed getting to know Chris better and I also enjoyed meeting Alison. Finally, we returned home and all went to bed, and at last I was alone with Jill. And so, I mustered up all my courage, and started The Conversation.

Gus: "So, I just wanted to say that I've really enjoyed the time we've spent together in New York, and I wanted to come down here to tell you that, and to say that I'd really like to see more of you, and I'm wondering how you feel about that."

(pause)

Jill: "Thanks."

(pause)

During that pause, which lasted probably a second in real time, but approximately 3 years in subjective time, the following images all crashed into my head at once (not making this up- I've always remembered this moment *very* vividly):

... the bases are loaded in sold-out Busch stadium. The fans are on their feet... it's the bottom of the 9th, down by a run, the bases are loaded, and Gus is at the plate with a full count. There is an announcer:

Announcer: "Here's the pitch... SWING, and a MISS! That's the ballgame!"

silence in the stands as Gus stands dejectedly at the plate...

... World War II... a B-22 bomber has just taken a hit and is streaming smoke and flame as it begins to plunge toward an anonymous death in the middle of the Pacific. Through the window of the cockpit we can see pilot Gus as he engages in a futile attempt to pull up...

... that scene from Pearl Harbor where the Arizona is slowly sinking, and those sailors are all trapped inside, and you can see their fingers sticking out of the grating as the water starts pouring in and the ship slips below the surface...


Then the pause ended, and Jill went on to explain that she was going to be extremely busy at work until her big event she had to plan (4 months away), and she tended to disappear on people, and that she sometimes used work to keep distance from people, and that "It's not you, it's me."

At that point, I almost laughed- I remember thinking "Oh my god, I'm in dating cliche hell: too busy at work, you know, for like, *ever*, it's-not-you-it's-me, oh god, please let this stop."

Finally, we just settled into an awkward silence, and I think she eventually fell asleep. As for me, I just lay there. All I could do was lay there thinking: I am so stupid. I mean, colossally, stupefyingly stupid. How could I have thought this would end any other way? The signs were all there. But no, I just had to come down here and humiliate myself, like a moth that gets really close to the flame, all the while thinking, "Gee, it sure is getting awfully hot. That can't be a good sign. But whatever, I just have to touch that light... I just have to... I just ha-" (death)

I did not sleep a wink the entire night. It seemed like the longest night of my life. When the sun finally started coming up and there was enough light in the room to read, that's what I did. Eventually, Jill woke up and said we ought to get out of bed and join Chris, and as she moved to do so, I reached out and touched her arm very lightly.

There are 2 things I'll always remember about that moment: first, the almost electric feeling of that tough, and second, the look that Jill gave me when I did it. It was a look with a lot of layers to it- I read in it that it had been as physically electric for her as it had been for me, that it had touched her emotionally, and that it scared her. Now, that's a lot to read into one brief moment, and by no means was I feeling particularly confident at that point about my ability to read Jill, but as I write this, I've had the benefit of some months for Jill and I to relive all those old moments, and tell each other what we each were thinking at the time. And it turns out I had that look mostly right.

But at the time I didn't know that, and the moment passed, so we went out to join Chris. I was just running out the clock, waiting until 10 for the cab to come and get me and take me back to NYC. I put on the happy face as much as I could until it was finally time to go. Jill walked me out, and I remember her standing there on the street watching me go as the cab pulled away. She looked as beautiful and inscrutable as ever.

As for me, I slumped down in my seat and began the odious process of Updating People. I had shared with a few people my grand intentions in going down there, and of course they all wanted to know how it had gone. I tried, not particularly successfully I'd imagine, not to let show how humiliated I felt, but I got through it and got home.

For the next few weeks, I listlessly went through my lessons and tried to focus on putting it all behind me. Around Christmastime, I went on a date and took her for a walk around the southern tip of Manhattan. It was a beautiful night, and New York City is at its most romantic (in my opinion) around Christmastime. But what I discovered as we went on this very romantic walk was that I could think only of Jill, and how much I'd like to take her on this walk.

When I got home, I decided that since I still couldn't get her out of my mind, I'd try to see if I could get a conversation going again with her. I was still confused about what had actually happened, especially given that she'd never actually said something like "I'm not interested in you," or "I only think of you as a friend" etc, etc. So I bought her a pair of wine glasses (since she'd complained once about having to drink wine out of paper cups at her apartment) under the guise of its being the holidays, and mailed them to her with a letter.

The letter worked, in the sense that we did end up having a conversation about it. We had a long phone call one night in early January, and in it, Jill for the first time shared some things about her past, and why it was hard for her to respond to what I was trying to offer her. The upshot of the conversation was: "It's not that I'm not interested, but I'm not in a place in my life where I can accept what you're offering me."

Me being me, I chose to focus a lot more on the "It's not that I'm not interested" part, and a lot less on the "I'm not in a place in my life where I can accept what you're offering me" part.

Though I hoped that that conversation would be the first of many conversations about what was going on in our lives, and how we might move closer together, it turned out to be the first of exactly one conversation. We slipped back into only the occasional email, and then in mid January I was offered the position of Director in the company, with the chance to move back to California and have the Bay Area territory. It was a tremendous opportunity, but I said I needed a little time to think about it.

Now, I knew that Jill loved California, and would more than likely be open to moving back there at some point, and so before I made a final decision, I thought I would try one more time to see if there was any chance that Jill and I might date.

Shortly thereafter, a chance to do that presented itself when Jonathan invited me down to DC for a concert. I contacted Jill and told her I would be in town, and asked if she wanted to get together for coffee or something. She met me at the metro station by her house, and we went for a long walk with her dog Jukebox, and then went back to her apartment. We talked for a long time, but I couldn't seem to steer the conversation to anything significant. Jill was a professional lobbyist on Capitol Hill, so I suppose I was overmatched in terms of trying to control a conversation, but I could tell she was keeping me at arm's length, and deliberately preventing the conversation from getting too close to anything like what we'd discussed on the phone, or even when I'd come down the last time.

In the end, I left without having talked about any of the things I'd hoped to. I had been searching for any reason to hope we might get together, and Jill was careful not to give me any. If she had, I would have gone back to NYC and said that I couldn't accept the Directorship for another 1-2 years; I was willing to do the bulk of the travel to DC to see Jill, and I was even willing to eventually transition to working half the time out of the DC office, until such a time as Jill was ready to move to CA. No one else was interested in either SF or San Diego, so I figured there would still be opportunities for a directorship in CA.

I never mentioned any of that stuff to Jill at the time; these are among the things that we have revealed to each other only as we have dated over the last 8 months. In any case, I went back to NYC and accepted the directorship in SF, and began making plans to move that summer.

Back in NYC, again moping my way through my lessons, I eventually decided to have a dinner party, and summon some of my close friends to tell them the story, and see what they had to say about it. So, over President's Day weekend, my sister, Dan, Shara, Joel, Ed, Jonathan, Jeffrey, and a few others gathered for a working dinner. I told the whole story, and then posed the question: "What do I do? Do I just write her off completely? Or do I continue to try and pursue her in some fashion, and if so, how?" Then I went in the kitchen and cooked for a while, while the group discussed the situation.

Even though I was in a different room, I could tell that the discussion was quite a spirited one. When I put dinner on the table, and we started eating, we went around the table and each person gave their recommendation. Interestingly, the entire range of possibilities was represented; there wasn't anything even close to a consensus. But it was great fun to listen to all the different perspectives, and by the time we were done, and had moved on to board games (which eventually saw my sister punching Ed in a fit of competitive frustration, which I think turned him on), I had made up my mind. I opted for a course different from any I'd heard, but which nevertheless was inspired by the discussion overall.

Over the next 10 weeks, I commenced a campaign based on the premise that the primary thing that was holding Jill and I back from dating each other was actually not a fundamental lack of feeling for me, but rather that she was scared of taking the chance on the relationship, only to have it not work out and end up getting hurt. Now, while I'd been pretty clear that I was interested, I had not really communicated the full extent of my interest in Jill. I'd kept that part somewhat close to the vest, wanting first to see how she would respond. But now, I thought, it's time for the Hail Mary pass. Desperate times call for desperate measures, and all that.

I knew that in 11 weeks I would see Jill at Chris's wedding, where she was to be Maid of Honor. So, I wrote a series of 5 letters in which I told the story of meeting her and going on the dates that we'd gone on, and how emotionally significant it all was to me. But, figuring that it would be hard to read that directly, I wrote the letters as a fairy tale in 5 parts, about a knight and a lady. I also made 5 mix CD's that functioned as a soundtrack to the 5 letters. I alternated between them, sending 1 letter or CD each week, which took us until the week before Chris's wedding.

I hoped that the letters would spark more dialogue between us, but I didn't hear from Jill until after I'd sent the last CD. She sent a letter, which arrived just a couple days before I left for LA for the wedding. It was, in many ways, a beautiful letter, which spoke back to me in the kind of language that I had used in my letters to her. But, it didn't say any of the things that I'd hoped it would. It prompted me to write [a letter back in response], but because I'd promised in my 5th letter that I would stop already with the letters and CDs, etc., and that I would stop pursuing her unless she gave me a clear signal to do otherwise, I instead FedEx'd it to myself, and put it away, thinking that if we ever did get together, I would surprise her with it as a gift.

So I went to Chris's wedding expecting that it would probably be the last time I ever saw her, and trying to take some comfort in the idea that I'd really tried, really given it my very best shot.

The wedding, it turns out, was a very dramatic affair. It was great to see Chris and John married, and the service was great. But Jill was not in a good place, and at one point just before the service, she walked up to me and said:

"I hate weddings. Promise me that when you get married, you won't ask me to be in your wedding."

And then she looked at me expectantly.

I thought about it for a second, and then I said:

"I'm sorry Jill, but I can't promise you that."

That turns out to have been one of my more prescient moments in life.

At the reception, Jill delivered her maid-of-honor speech, which is outside the scope of this blog, but which is legendary in its own right. It was a pretty spectacular public self-immolation, and the echoes of it still ring down through the ages. Afterward, Jill largely disappeared (insofar as I could tell), and I took refuge on the dance floor, where I could forget about all that had transpired. I didn't see her again until almost the end of the last song. I'd hoped to get one dance with her, but it seemed it was not meant to be.

And then, the DJ put on one more song, to play while he packed up. It was: Don't Stop Believin.

There's so much we don't understand about how the universe works, and I've often marveled at how *that* particular song was the one the DJ chose to play. We danced together, essentially alone, since everyone else was filing out of the reception hall, and we sang along to the song. It was... fun. And I wanted to say that if she would just say the word, it could be like that all the time, but I'd promised to give her space that night, and so I kept quiet.

There was a long after party that night, and I had a good time. Jill and I didn't really speak to each other, but I did look over her way a lot, and it sure seemed like she was looking over at me a lot. But eventually the party wound down, and with a perfunctory hug goodbye, I went back to my room, fully expecting never to see or possibly even hear from her again.

The next morning, I laid in my bed in the hotel room and tossed and turned. Finally, in an effort to get everything that was in my head out of my head, I wrote [another letter to Jill], which I also ended up FedEx-ing to myself, rather than actually sending to her. When I got back to NYC, I threw it in the closet with the other one.

In the meantime, I drove up to JOC's house that day, and he and I had a long conversation about all that had happened. I was on my way to the Bay Area to scout places to live, and a place to put the office. Since JOC's house was halfway to the Bay Area, I spent the night there. He was very supportive, and since he'd known Jill pretty well for several years, he was able to help me make some sense out of everything.

That night, around 3am, my phone went off. I'd gotten a text. I rolled over and picked it up, expecting it to be Kiddo or one of my other students. Instead, it was from Jill. Although the text was itself innocuous, I had the sense that it was a trial balloon kind of text, as if to see if I would respond at all. And I laid there for a couple of minutes trying to figure out if I wanted to respond, given all that had happened.

In the end, I figured that Jill needed more people in her life who would support her. And I thought that if I couldn't date her, well, at least I could provide her steady friendship and support. The truth was, I still loved her enough that that was better than nothing. So I did respond. She was in the airport in Atlanta on her way back to DC.

When I finally arrived in the Bay Area the next day, I did a lot of looking at office spaces, and even interviewed with the guy at Google who controls all their real estate and office space (thanks to L, who set that up). By the middle of the afternoon, I was sure I'd put a stake down in Palo Alto, and so I turned my thoughts to where I'd want to live.

Since I'd spent the last couple years living literally across 2nd avenue from the office, my first thought was that I'd do something similar, and try to find an apartment as close as possible to the office. But then I remembered Half Moon Bay, which I'd driven through in college with Joel and Z-man, and so I decided to take a drive to the beach.

When I got there, HMB was showing her very best self. It was sunny and 72 degrees, and I went for a walk down on the sand. I sat down, and texted Jill that I was sitting on the beach in HMB. She responded with something "omg, that's my mom's favorite place in the whole world! What are you doing THERE?"

At that point, I'd been on the fence about whether I should live close to the office, or maybe look for a place near the beach. But when I got Jill's text, it tipped me. I decided that when I moved out to CA, I'd look and see if I could find a place in HMB. So, in a very real way I ended up in HMB because of Jill, and so it's only fitting that we are getting married there next year.

The next day, I went back to NYC. I was very sad, but I knew it was time to put it all behind me and move on. And that's what I did. A couple months later I met Keiko, fell in love again, and over time, healed. Along the way, Jill and I would email perhaps once a month, and let each other know what was going on in our lives, so we stayed in touch. I watched as she moved away from DC, which was a toxic environment for her, got control of her life, and moved on in her own way. 2 years passed like that.

Then Keiko and I broke up. It was a very hard breakup, and I was miserable for about 4 months. Somewhere in that time, Jill invited me to go meet her and Alison in Belize over New Year's. Needing to do something fun, and figuring enough time had passed that we could see each other in a healthy way, I agreed.

And then everything changed.